Organic chemistry Books

Book SynopsisThe current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume.

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Book SynopsisIntroduction to Soft Matter, Revised Edition: Synthetic and Biological Self-Assembling Materials provides an introduction to this exciting subject with chapters covering natural and synthetic polymers, colloids, surfactants, and liquid crystals highlighting the many and varied applications of these materials.Trade Review"It is quite amazing how well Hamley actually presents and explains the large number of examples." (CHOICE, April 2008)Table of ContentsPreface to the Revised Edition. Preface to the First Edition. 1. Introduction. 1.1Introduction. 1.2 Intermolecular Interactions. 1.3 Structural Organization. 1.4 Dynamics. 1.5 Phase Transitions. 1.6 Order Parameters. 1.7 Scaling Laws. 1.8 Polydispersity. 1.9 Experimental Techniques for Investigating Soft Matter. 1.10 Computer Simulation. Further Reading. 2. Polymers. 2.1 Introduction. 2.2 Synthesis. 2.3 Polymer Chain Conformation. 2.4 Characterization. 2.5 Polymer Solutions. 2.6 Amorphous Polymers. 2.7 Crystalline Polymers. 2.8 Plastics. 2.9 Rubber. 2.10 Fibres. 2.11 Polymer Blends and Block Copolymers. 2.12 Dendrimers and Hyperbranched Polymers. 2.13 Polyelectrolytes. 2.14 Electronic and Opto-Electronic Polymers. Further Reading. Questions. 3. Colloids. 3.1 Introduction. 3.2 Types of Colloids. 3.3 Forces between Colloidal Particles. 3.4 Characterization of Colloids. 3.5 Charge Stabilization. 3.6 Steric Stabilization. 3.7 Effect of Polymers on Colloid Stability. 3.8 Kinetic Properties. 3.9 Sols. 3.10 Gels. 3.11 Clays. 3.12 Foams. 3.13 Emulsions. 3.14 Food Colloids. 3.15 Concentrated Colloidal Dispersions. Further Reading. Questions. 4. Amphiphiles. 4.1 Introduction. 4.2 Types of Amphiphile. 4.3 Surface Activity. 4.4 Surfactant Monolayers and Langmuir-Blodgett Films. 4.5 Adsorption at Solid Interfaces. 4.6 Micellization and the Critical Micelle Concentration. 4.7 Detergency. 4.8 Solubilization in Micelles. 4.9 Interfacial Curvature and Its Relationship to Molecular Structure. 4.10 Liquid Crystal Phases at High Concentrations. 4.11 Membranes. 4.12 Templated Structures. Further Reading. Questions. 5. Liquid Crystals. 5.1 Introduction. 5.2 Types of Liquid Crystals. 5.3 Characteristics of Liquid Crystal Phases. 5.4 Identification of Liquid Crystal Phases. 5.5 Orientational Order. 5.6 Elastic Properties. 5.7 Phase Transitions in Liquid Crystals. Further Reading. Questions. 6. Biological Soft Matter Science. 6.1 Introduction. 6.2 Lipid Membranes. 6.3 DNA. 6.4 Proteins. 6.5 Polysaccharides and Glycoproteins. 6.6 Macromolecular Assemblies. Further Reading. Questions. Numerical Solutions to Questions. Index.

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Book SynopsisThis book provides an introduction to this exciting and relatively new subject with chapters covering natural and synthetic polymers, colloids, surfactants and liquid crystals highlighting the many and varied applications of these materials. Written by an expert in the field, this book will be an essential reference for people working in both industry and academia and will aid in understanding of this increasingly popular topic. Contains a new chapter on biological soft matter Newly edited and updated chapters including updated coverage of recent aspects of polymer science. Contain problems at the end of each chapter to facilitate understanding Trade Review"...Introduction to Soft Matter is an extremely valuable textbook for undergraduate classes, and represents an excellent introductory reading for the researchers who venture on this field." (Macromol. Chem. Phys. 2008, 209, 1073)Table of ContentsPreface to the revised Edition. Preface to the First Edition. 1. Introduction. 1.1 Introduction. 1.2 Intermolecular Interactions. 1.3 Structural Organization. 1.4 Dynamics. 1.5 Phase Transitions. 1.6 Order Parameters. 1.7 Scaling Laws. 1.8 Polydispersity. 1.9 Experimental Techniques for Investigating Soft Matter. 1.10 Computer Simulation. Further Reading. 2. Polymers. 2.1 Introduction. 2.2 Synthesis. 2.3 Polymer Chain Conformation. 2.4 Characterization. 2.5 Polymer Solutions. 2.6 Amorphous Polymers. 2.7 Crystalline Polymers. 2.8 Plastics. 2.9 Rubber. 2.10 Fibres. 2.11 Polymer Blends and Block Copolymers. 2.12 Dendrimers and Hyperbranched Polymers. 2.13 Polyelectrolytes. 2.14 Electronic and Opto-electronic Polymers. Further Reading. Questions. 3. Colloids. 3.1 Introduction. 3.2 Types of Colloids. 3.3 Forces Between Colloidal Particles. 3.4 Characterization of Colloids. 3.5 Charge Stabilization. 3.6 Steric Stabilization. 3.7 Effect of Polymers on Colloid Stability. 3.8 Kinetic Properties. 3.9 Sols. 3.10 Gels. 3.11 Clays. 3.12 Foams. 3.13 Emulsions. 3.14 Food Colloids. 3.15 Concentrated Colloidal Dispersions. Further Reading. Questions. 4. Amphiphiles. 4.1 Introduction. 4.2 Types of Amphiphile. 4.3 Surface Activity. 4.4 Surfactant Monolayers and Langmuir-Blodgett Films. 4.5 Adsorption at Solid Interfaces. 4.6 Micellization and the Critical Micelle Concentration. 4.7 Detergency. 4.8 Solubilization in Micelles. 4.9 Interfacial Curvature and Its Relationship to Molecular Structure. 4.10 Liquid Crystal Phases at High Concentrations. 4.11 Membranes. 4.12 Templated Structures. Further Reading. Questions. 5. Liquid Crystals. 5.1 Introduction. 5.2 Types of Liquid Crystals. 5.3 Characteristics of Liquid Crystal Phases. 5.4 Identification of Liquid Crystal Phases. 5.5 Orientational Order. 5.6 Elastic Properties. 5.7 Phase Transitions in Liquid Crystals. 5.8 Applications of Liquid Crystals. Further Reading. Questions. 6. Biological Soft Matter. 6.1 Introduction. 6.2 Lipid Membranes. 6.3 DNA. 6.4 Proteins. 6.5 Polysaccharides and Glycoproteins. 6.6 Macromolecular Assemblies. Further Reading. Questions. Numerical Solutions to Questions. Index.

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Book SynopsisThe ultimate reference guide to the synthesis of radiopharmaceuticals The Radiochemical Syntheses series provides scientists and professionals with a comprehensive reference to proven synthetic methods for radiochemical reactions, along with step-by-step guidance on how to replicate these syntheses in the laboratory. Volume 1 in the series focuses on the synthesis and purification of radiopharmaceuticals in clinical use today. It brings together in one complete, self-contained volume a collection of monographs containing a wealth of practical information from across the literature, demonstrating in meticulous detail how to prepare radiopharmaceuticals for positron emission tomography (PET) imaging, especially in tumor studies, cardiology, and neuroscience. Readers have key experimental details culled from the literature at their fingertips, greatly simplifying the process of qualifying a site for the clinical production of new radiopharmaceuticals.Table of ContentsContributors ix Foreword xvii Preface xix Abbreviations xxi Part I Fluorine-18 Labeled Radiopharmaceuticals 1 1. Synthesis of [18F]-Fluorodeoxyglucose ([18F]FDG) 3Michelle L. Richards and Peter J. H. Scott 2. Synthesis of Sodium [18F]Fluoride (Na[18F]F) 15Brian G. Hockley and Peter J. H. Scott 3. Radiosynthesis of 3_-Deoxy-3_-[18F]Fluorothymidine ([18F]FLT) 21Hartmuth C. Kolb, Henry C. Padgett, Steve Zigler, Jim Patanella, Fanrong Mu, Umesh B. Gangadharmath, Vani P. Mocharla, Peter J. H. Scott, and Joseph C. Walsh 4. Synthesis of [18F]Fluoroazomycin Arabinoside ([18F]FAZA) 31Brian G. Hockley and Peter J. H. Scott 5. Synthesis of [18F]Fluoromisonidazole (1-(2-Hydroxy-3-[18F]Fluoropropyl)-2-Nitroimidazole, [18F]FMISO) 41Patrick J. Riss, Valentina Ferrari, Robert Bielik, Roberto Canales-Candela, Rob Smith, and Franklin I. Aigbirhio 6. Synthesis of [18F]FPPRGD2 51Shuanglong Liu, Frederick T. Chin, Zhen Cheng, and Xiaoyuan Chen 7. Synthesis of [18F]Fluorocholine ([18F]FCH) 61David Kryza 8. Clinical Manufacturing of [18F]-16-α-Fluoroestradiol ([18F]FES) 69Piyush Kumar and John R. Mercer 9. Synthesis of N-Succinimidyl 4-[18F]Fluorobenzoate ([18F]SFB) 81Xia Shao 10. Synthesis of 4-(2_-Methoxyphenyl)-1-[2_-(N-2__Pyridinyl)-p-[18F]Fluorobenzamido]Ethylpiperazine [18F]MPPF 87Marion Alvarez and Didier Le Bars 11. Synthesis of [18F]-Fallypride 95Laurent Brichard, Valentina Ferrari, Rob Smith, and Franklin I. Aigbirhio 12. Synthesis of [18F]Fluoroethyltyrosine (18F-FET) 103Yi Zhao, Amar Alfteimi, and Maaz Zuhayra 13. Synthesis of [18F]Flumazenil ([18F]FZ) 111Ralf Schirrmacher, Alexey Kostikov, Gassan Massaweh, Miriam Kovacevic, Carmen Wängler, and Alexander Thiel 14. Synthesis of 6-[18F]Fluorodopamine (6-[18F]FDA) 125Michael A. Channing, John L. Musachio, and Jozef J. Kusmierz 15. Synthesis of 2-([18F]Fluoro)-3-[(2S)-2-Azetidinylmethoxy]Pyridine ([18F]2FA) 139Hayden T. Ravert, Daniel P. Holt, and Robert F. Dannals 16. Synthesis of [18F]-Substance-P Antagonist-Receptor Quantifier ([18F]SPA-RQ) 155Sofie Celen, Kim Serdons, Tjibbe de Groot, Terence G. Hamill, and Guy Bormans Part II Carbon-11 Labeled Radiopharmaceuticals 167 17. Synthesis of [11C]Choline Chloride ([11C]CHL) 169Brian G. Hockley, Bradford Henderson, and Xia Shao 18. Synthesis of 2-(4-N-[11C]Methylaminophenyl)-6-Hydroxybenzothiazole ([11C]6-OH-BTA-1; [11C]PIB) 177Cécile Philippe, Markus Mitterhauser, and Wolfgang Wadsak 19. Synthesis of [11C]-meta-Hydroxyephedrine ([11C]MHED) 191Filippo Lodi, Assunta Carpinelli, Claudio Malizia, and Stefano Boschi 20. Synthesis of l-[methyl-11C]Methionine ([11C]MET) 199Amy L. Vāvere and Scott E. Snyder 21. Synthesis of (+)-α-[11C]Dihydrotetrabenazine ([11C]DTBZ) 213Michael R. Kilbourn 22. Synthesis of [11C]Flumazenil([11C]FMZ) 221Roberto Canales-Candela, Patrick J. Riss, and Franklin I. Aigbirhio 23. Synthesis of [11C]Hexadecanoic Acid ([11C]Palmitic Acid) 233Adam C. Runkle, Xia Shao, and Peter J. H. Scott 24. Synthesis of O-methyl-11C]Metomidate ([11C]-MTO) 245István Boros and Franklin I. Aigbirhio 25. Synthesis of [11C]Carfentanil ([11C]CFN) 257Louis Tluczek and Xia Shao 26. Synthesis of [carbonyl-11C]Way-100635 265Jan D. Andersson, Sangram Nag, Raisa N. Krasikova, Victor W. Pike, and Christer Halldin 27. Synthesis of [11C]Raclopride 275Xia Shao 28. Synthesis of 3-Amino-4-[2-(N-Methyl-N-[11C]Methyl-Amino-Methyl)Phenylsulfanyl]-Benzonitrile ([11C]Dasb) 285Daniela Haeusler, Markus Mitterhauser, and Wolfgang Wadsak 29. Synthesis of [11C] Acetate 297Filippo Lodi, Claudio Malizia, and Stefano Boschi 30. Synthesis of N-(2-[11C]Methoxybenzyl)-N-(4-Phenoxypyridin-3-yl)Acetamide ([11C]PBR28) 305Qi-Huang Zheng, Min Wang, and Bruce H. Mock Part III Other Radiopharmaceuticals 313 31. Synthesis of [13N]Ammonia ([13N]NH3) 315Peter J. H. Scott 32. Synthesis of [68GA]Gallium Dota-(TYR3)-Octreotide Acetate ([68GA]-Dotatoc) 321Harald Eidherr, Friedrich Girschele, Markus Mitterhauser, and Wolfgang Wadsak Appendix 1 Supplier Information 335 Index 339

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Book SynopsisFirst published over 40 years ago, this was the first text on the identification of organic compounds using spectroscopy. This text presents a unified approach to the structure determination of organic compounds based largely on mass spectrometry, infrared (IR) spectroscopy, as well as multinuclear and multidimensional nuclear magnetic resonance (NMR) spectroscopy. The key strength of this text is the extensive set of practice and real-data problems (in Chapters 7 and 8). Even professional chemists use these spectra as reference data. Spectrometric Identification of Organic Compounds is written by and for organic chemists, and emphasizes the synergistic effect resulting from the interplay of spectra. This text is characterized by its problem-solving approach with numerous practice problems and extensive reference charts and tables.Table of ContentsCHAPTER 1 MASS SPECTROMETRY 1 1.1 Introduction 1 1.2 Instrumentation 2 1.3 Ionization Methods 3 1.4 Mass Analyzers 8 1.5 Interpretation of EI Mass Spectra 12 1.6 Mass Spectra of Some Chemical Classes 18 References 37 Student Exercises 37 Appendices 46 A Formula Masses (FM) for Various Combinations of Carbon, Hydrogen, Nitrogen, and Oxygen 46 B Common Fragment Ions 67 C Common Fragments Lost 69 CHAPTER 2 INFRARED SPECTROSCOPY 71 2.1 Introduction 71 2.2 Theory 71 2.3 Instrumentation 76 2.4 Sample Handling 77 2.5 Interpretation of Spectra 78 2.6 Characteristic Group Absorptions of Organic Molecules 81 References 108 Student Exercises 108 Appendices 118 A Transparent Regions of Solvents and Mulling Oils 118 B Characteristic Group Absorptions 119 C Absorptions for Alkenes 124 D Absorptions for Phosphorus Compounds 125 E Absorptions for Heteroaromatics 125 CHAPTER 3 PROTON (1H) MAGNETIC RESONANCE SPECTROSCOPY 126 3.1 Introduction 126 3.2 Theory 126 3.3 Instrumentation and Sample Handling 129 3.4 Chemical Shift 132 3.5 Spin-Spin Coupling, Multiplets, and Spin Systems 137 3.6 Protons on Oxygen, Nitrogen, and Sulfur Atoms:Exchangeable Protons 144 3.7 Coupling of Protons to Other Important Nuclei (19F, D (2H), 31P, 29Si, and 13C) 149 3.8 Chemical Equivalence 150 3.9 Magnetic Equivalence 154 3.10 AMX, ABX, and ABC Rigid Systems with Three Coupling Constants 155 3.11 Weakly and Strongly Coupled Systems: Virtual Coupling 156 3.12 Chirality 158 3.13 Magnitude of Vicinal and Geminal Coupling Constants 160 3.14 Long-Range Coupling 162 3.15 Selective Spin Decoupling: Double Resonance 162 3.16 Nuclear Overhauser Effect 162 3.17 Conclusion 163 References 164 Student Exercises 164 Appendices 175 A Chart A.1: Chemical Shifts of Protons on a Carbon Atom Adjacent (𝛼 Position) to a Functional Group in Aliphatic Compounds (M–Y) 175 Chart A.2: Chemical Shifts of Protons on a Carbon Atom Once Removed (𝛽 Position) from a Functional Group in Aliphatic Compounds (M–C–Y) 177 B Effect on Chemical Shifts by Two or Three Directly Attached Functional Groups 178 C Chemical Shifts in Alicyclic and Heterocyclic Rings 180 D Chemical Shifts in Unsaturated and Aromatic Systems 181 Chart D.1: Chemical Shifts of Protons on Monosubstituted Benzene Rings 183 E Protons Subject to Hydrogen-Bonding Effects (Protons on Heteroatoms) 184 F Proton Spin-Spin Coupling Constants 185 G Chemical Shifts and Multiplicities of Residual Protons in Commercially Available Deuterated Solvents 187 H Chemical Shifts of Common Laboratory Solvents as Trace Impurities 188 I Proton NMR Chemical Shifts of Amino Acids in D2O 190 CHAPTER 4 CARBON-13 NMR SPECTROSCOPY 191 4.1 Introduction 191 4.2 Theory 191 4.3 Interpretation of a Simple 13C NMR Spectrum: Diethyl Phthalate 198 4.4 Quantitative 13C Analysis 198 4.5 Chemical Equivalence 200 4.6 DEPT 200 4.7 Chemical Classes and Chemical Shifts 203 4.7.1 Alkanes 204 4.7.1.1 Linear and Branched Alkanes 204 4.7.1.2 Effect of Substituents on Alkanes 205 4.7.1.3 Cycloalkanes and Saturated Heterocyclics 205 4.7.2 Alkenes 206 4.7.3 Alkynes 208 4.7.4 Aromatic Compounds 208 4.7.5 Heteroaromatic Compounds 209 4.7.6 Alcohols 209 4.7.7 Ethers, Acetals, and Epoxides 209 4.7.8 Halides 211 4.7.9 Amines 211 4.7.10 Thiols, Sulfides, and Disulfides 211 4.7.11 Functional Groups Containing Carbon 211 4.7.11.1 Ketones and Aldehydes 212 4.7.11.2 Carboxylic Acids, Esters, Chlorides, Anhydrides, Amides, and Nitriles 214 4.7.11.3 Oximes 214 References 214 Student Exercises 214 Appendices 225 A The 13C Chemical Shifts, Coupling Constants, and Peak Multiplicities of Common Deuterated NMR Solvents 225 B 13C Chemical Shifts of Common Laboratory Solvents as Trace Impurities in Selected Deuterated NMR Solvents 226 C 13C Chemical Shift Ranges for Chemical Classes 227 D 13C Chemical Shifts (ppm) for Several Natural Products 229 CHAPTER 5 TWO-DIMENSIONAL NMR SPECTROSCOPY 230 5.1 Introduction 230 5.2 Theory 231 5.3 Correlation Spectroscopy 233 5.3.1 1H-1H Correlation: COSY 235 5.4 Ipsenol: 1H-1H COSY 235 5.4.1 Ipsenol: Double Quantum Filtered 1H-1H COSY 238 5.4.2 Carbon Detected 13C-1H COSY: HETCOR 238 5.4.3 Proton Detected 1H-13C COSY: HMQC 239 5.4.4 Ipsenol: HETCOR and HMQC 239 5.4.5 Ipsenol: Proton-Detected, Long-Range 1H-13C Heteronuclear Correlation: HMBC 241 5.5 Caryophyllene Oxide 243 5.5.1 Caryophyllene Oxide: DQF-COSY 243 5.5.2 Caryophyllene Oxide: HMQC 243 5.5.3 Caryophyllene Oxide: HMBC 247 5.6 13C-13C Correlations: INADEQUATE 249 5.6.1 INADEQUATE: Caryophyllene Oxide 251 5.7 Lactose 251 5.7.1 DQF-COSY: Lactose 251 5.7.2 HMQC: Lactose 254 5.7.3 HMBC: Lactose 254 5.8 Relayed Coherence Transfer: TOCSY 254 5.8.1 2D TOCSY: Lactose 254 5.8.2 1D TOCSY: Lactose 257 5.9 HMQC-TOCSY 259 5.9.1 HMQC-TOCSY: Lactose 259 5.10 ROESY 259 5.10.1 ROESY: Lactose 259 5.11 VGSE 262 5.11.1 COSY: VGSE 262 5.11.2 TOCSY: VGSE 262 5.11.3 HMQC: VGSE 262 5.11.4 HMBC: VGSE 264 5.11.5 ROESY: VGSE 265 5.12 Pulsed Field Gradient NMR 265 References 268 Student Exercises 268 CHAPTER 6 MULTINUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 298 6.1 Introduction and General Considerations 298 6.2 15N Nuclear Magnetic Resonance 299 6.3 19F Nuclear Magnetic Resonance 306 6.4 29Si Nuclear Magnetic Resonance 309 6.5 31P Nuclear Magnetic Resonance 312 6.6 Conclusions 315 References 315 Student Exercises 315 Appendix 320 A Properties of Magnetically Active Nuclei 320 CHAPTER 7 SOLVED PROBLEMS 325 7.1 Introduction 325 Problem 7.1 Discussion 329 Problem 7.2 Discussion 333 Problem 7.3 Discussion 337 Problem 7.4 Discussion 344 Problem 7.5 Discussion 350 Problem 7.6 Discussion 356 Student Exercises 357 CHAPTER 8 ASSIGNED PROBLEMS 364 8.1 Introduction 364 INDEX 453

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Book SynopsisThis book focuses on the drug discovery and development applications of transition metal catalyzed processes, which can efficiently create preclinical and clinical drug candidates as well as marketed drugs. The authors pay particular attention to the challenges of transitioning academically-developed reactions into scalable industrial processes. Additionally, the book lays the groundwork for how continued development of transition metal catalyzed processes can deliver new drug candidates. This work provides a unique perspective on the applications of transition metal catalysis in drug discovery and development it is a guide, a historical prospective, a practical compendium, and a source of future direction for the field.Trade Review“The book will be particularly appreciated by young scientists, especially those aspiring to a future in the pharmaceutical industry, because it shows what kind of problems they will be asked to solve once they start their industrial career.” (ChemMedChem, 1 March 2013) “All chapters are well-written and comprehensive with lots of examples from OPR and D. The book is highly recommended to all process chemists.” (Organic Process Research & Development Journal, 1 November 2012)Table of ContentsPreface vii Contributors ix About the Authors xi 1 Transition Metal Catalysis in the Pharmaceutical Industry 1Carl A. Busacca, Daniel R. Fandrick, Jinhua J. Song, and Chris H. Senanayake (Boehringer Ingelheim Pharmaceuticals) 2 Selected Applications of Transition Metal-Catalyzed Carbon–Carbon Cross-Coupling Reactions in the Pharmaceutical Industry 25Hong C. Shen (Roche) 3 Selected Applications of Pd- and Cu-Catalyzed Carbon–Heteroatom Cross-Coupling Reactions in the Pharmaceutical Industry 97Jingjun Yin (Merck) 4 Asymmetric Cross-Coupling Reactions 165Vince Yeh (Novartis) and William A. Szabo (Consultant in Drug Development) 5 Metathesis Reactions 215Oliver R. Thiel (Amgen) 6 Transition Metal-Catalyzed Synthesis of Five- and Six-Membered Heterocycles 257Cheol K. Chung (Merck) and Matthew L. Crawley (Main Line Health) 7 Oxidative Catalysis 277Lamont Terrell (GlaxoSmithKline) 8 Industrial Asymmetric Hydrogenation 315Hans-Ulrich Blaser (Solvias) Index 243

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Book SynopsisOne approach to organic synthesis is retrosynthetic analysis. With this approach chemists start with the structures of their target molecules and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials.Trade Review"The book provides an excellent and pragmatic panorama of the various aspects of disconnective strategies, whilst keeping in mind the importance of protective strategies." (Reviews, December 2010) Table of ContentsPreface vii General References ix 1. The Disconnection Approach 1 2. Basic Principles: Synthons and Reagents: Synthesis of Aromatic Compounds 5 3. Strategy I: The Order of Events 11 4. One-Group C–X Disconnections 15 5. Strategy II: Chemoselectivity 21 6. Two-Group C–X Disconnections 29 7. Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategy 35 8. Amine Synthesis 41 9. Strategy IV: Protecting Groups 49 10. One-Group C–C Disconnections I: Alcohols 55 11. General Strategy A: Choosing a Disconnection 61 12. Strategy V: Stereoselectivity A 67 13. One-Group C–C Disconnections II: Carbonyl Compounds 75 14. Strategy VI: Regioselectivity 81 15. Alkene Synthesis 87 16. Strategy VII: Use of Acetylenes (Alkynes) 93 17. Two-Group C–C Disconnections I: Diels-Alder Reactions 99 18. Strategy VIII: Introduction to Carbonyl Condensations 105 19. Two-Group C–C Disconnections II: 1,3-Difunctionalised Compounds 111 20. Strategy IX: Control in Carbonyl Condensations 115 21. Two-Group C–C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation 123 22. Strategy X: Aliphatic Nitro Compounds in Synthesis 129 23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds 133 24. Strategy XI: Radical Reactions in Synthesis 139 25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds 147 26. Strategy XII: Reconnection 153 27. Two-Group C–C Disconnections VI: 1,6-diCarbonyl Compounds 159 28. General Strategy B: Strategy of Carbonyl Disconnections 165 29. Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocycles 173 30. Three-Membered Rings 181 31. Strategy XIV: Rearrangements in Synthesis 189 32. Four-Membered Rings: Photochemistry in Synthesis 195 33. Strategy XV: The Use of Ketenes in Synthesis 201 34. Five-Membered Rings 207 35. Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings 213 36. Six-Membered Rings 221 37. General Strategy C: Strategy of Ring Synthesis 227 38. Strategy XVII: Stereoselectivity B 235 39. Aromatic Heterocycles 245 40. General Strategy D: Advanced Strategy 255 Index 263

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Book SynopsisOne approach to organic synthesis is retrosynthetic analysis. With this approach a chemist will start with the structure of their target molecule and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials.Trade Review?The authors have succeeded admirably in the updating of a classic in the pedagogy of organic chemistry.? ( Journal of Medicinal Chemistry , August 2009) ?This book is suitable for advanced undergraduate students, researchers and professional chemists. Both the writing and the diagrams are simple and clear.? ( Reviews, May 2009)Table of ContentsPreface ix General References xi 1. The Disconnection Approach 1 2. Basic Principles: Synthons and Reagents Synthesis of Aromatic Compounds 7 3. Strategy I: The Order of Events 17 4. One-Group C–X Disconnections 23 5. Strategy II: Chemoselectivity 29 6. Two-Group C–X Disconnections 35 7. Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategy 45 8. Amine Synthesis 53 9. Strategy IV: Protecting Groups 61 10. One Group C–C Disconnections I: Alcohols 69 11. General Strategy A: Choosing a Disconnection 77 12. Strategy V: Stereoselectivity A 83 13. One Group C–C Disconnections II: Carbonyl Compounds 93 14. Strategy VI: Regioselectivity 101 15. Alkene Synthesis 107 16. Strategy VII: Use of Acetylenes (Alkynes) 115 17. Two-Group C–C Disconnections I: Diels-Alder Reactions 121 18. Strategy VIII: Introduction to Carbonyl Condensations 129 19. Two-Group C–C Disconnections II: 1,3-Difunctionalised Compounds 133 20. Strategy IX: Control in Carbonyl Condensations 139 21. Two-Group C–C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation 151 22. Strategy X: Aliphatic Nitro Compounds in Synthesis 161 23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds 167 24. Strategy XI: Radical Reactions in Synthesis 177 25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds 185 26. Strategy XII: Reconnection 193 27. Two-Group C–C Disconnections VI: 1,6-diCarbonyl Compounds 199 28. General Strategy B: Strategy of Carbonyl Disconnections 207 29. Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocycles 217 30. Three-Membered Rings 229 31. Strategy XIV: Rearrangements in Synthesis 237 32. Four-Membered Rings: Photochemistry in Synthesis 245 33. Strategy XV: The Use of Ketenes in Synthesis 251 34. Five-Membered Rings 255 35. Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings 261 36. Six-Membered Rings 269 37. General Strategy C: Strategy of Ring Synthesis 279 38. Strategy XVII: Stereoselectivity B 289 39. Aromatic Heterocycles 301 40. General Strategy D: Advanced Strategy 313 Index 325

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Book SynopsisWinner of the PROSE Award for Chemistry & Physics 2010 Acknowledging the very best in professional and scholarly publishing, the annual PROSE Awards recognise publishers'' and authors'' commitment to pioneering works of research and for contributing to the conception, production, and design of landmark works in their fields. Judged by peer publishers, librarians, and medical professionals, Wiley are pleased to congratulate Professor Ian Fleming, winner of the PROSE Award in Chemistry and Physics for Molecular Orbitals and Organic Chemical Reactions. Molecular orbital theory is used by chemists to describe the arrangement of electrons in chemical structures. It is also a theory capable of giving some insight into the forces involved in the making and breaking of chemical bondsthe chemical reactions that are often the focus of an organic chemist''s interest. Organic chemists with a serious interest in understanding and explaining their work usually express their Trade Review"Fleming uses nonquantitative molecular orbital theory to explain many common phenomena in organic chemistry. As such, this is a very powerful tool for students of advanced organic chemistry. Much of what is taken simply on faith or with some hand waving in sophomore organic chemistry can be readily explained with molecular orbital theory, which is usually considered too advanced for students at that level. Though this book could be used as theprimary textbook for a course solely on molecular orbitals in organic chemistry, it will more likely be used as a reference source for an advanced organic chemistry course for upper-level undergraduates or graduate students." (CHOICE, August 2010) "The new 'Fleming' is a must for every lecturer and every student of chemistry—a fantastic book. In this new form the textbook will last for another 30 years and remain as fresh as did its predecessor!" (Angewandte Chemie International Edition March 2010)Table of ContentsPreface. 1 Molecular Orbital Theory. 1.1 The Atomic Orbitals of a Hydrogen Atom. 1.2 Molecules made from Hydrogen Atoms. 1.3 C—H and C—C Bonds. 1.4 Conjugation—Hückel Theory. 1.5 Aromaticity. 1.6 Strained σ Bonds—Cyclopropanes and Cyclobutanes. 1.7 Heteronuclear Bonds, C—M, C—X and C=O. 1.8 The Tau Bond Model. 1.9 Spectroscopic Methods. 1.10 Exercises. 2 The Structures of Organic Molecules. 2.1 The Effects of π Conjugation. 2.2 σ Conjugation—Hyperconjugation. 2.3 The Configurations and Conformations of Molecules. 2.4 Other Noncovalent Interactions. 2.5 Exercises. 3 Chemical Reactions—How Far and How Fast. 3.1 Factors Affecting the Position of an Equilibrium. 3.2 The Principle of Hard and Soft Acids and Bases (HSAB). 3.3 Transition Structures. 3.4 The Perturbation Theory of Reactivity. 3.5 The Salem-Klopman Equation. 3.6 Hard and Soft Nucleophiles and Electrophiles. 3.7 Other Factors Affecting Chemical Reactivity. 4 Ionic Reactions—Reactivity. 4.1 Single Electron Transfer (SET) in Ionic Reactions. 4.2 Nucleophilicity. 4.3 Ambident Nucleophiles. 4.4 Electrophilicity. 4.5 Ambident Electrophiles. 4.6 Carbenes. 4.7 Exercises. 5 Ionic Reactions—Stereochemistry. 5.1 The Stereochemistry of the Fundamental Organic Reactions. 5.2 Diastereoselectivity. 5.3 Exercises. 6 Thermal Pericyclic Reactions. 6.1 The Four Classes of Pericyclic Reactions. 6.2 Evidence for the Concertedness of Bond Making and Breaking. 6.3 Symmetry-Allowed and Symmetry-Forbidden Reactions. 6.4 Explanations for the Woodward-Hoffmann Rules. 6.5 Secondary Effects. 6.6 Exercises. 7 Radical Reactions. 7.1 Nucleophilic and Electrophilic Radicals. 7.2 The Abstraction of Hydrogen and Halogen Atoms. 7.3 The Addition of Radicals to π Bonds 7.4 Synthetic Applications of the Chemoselectivity of Radicals. 7.5 Stereochemistry in some Radical Reactions. 7.6 Ambident Radicals. 7.7 Radical Coupling. 7.8 Exercises. 8 Photochemical Reactions. 8.1 Photochemical Reactions in General. 8.2 Photochemical Ionic Reactions. 8.3 Photochemical Pericyclic Reactions and Related Stepwise Reactions. 8.4 Photochemically Induced Radical Reactions. 8.5 Chemiluminescence. 8.6 Exercises. References. Index.

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Book SynopsisThis book will be mainly focussed on the properties and uses of dendrimers and dendrons. The aim of this book is to be the reference book about dendrimers applications. It will not describe all details, but it will give the reader a unique overview of what has currently been done with dendrimers, with numerous references and illustrations. It will be divided in four main parts: Part 1) Generalities, syntheses, characterizations and properties; Part 2) Applications in catalysis; Part 3) Applications for the elaboration or modification of materials; and Part 4) Applications in biology/medicine. The role of the nanometric size and the multiple functions of dendrimers on the properties will be emphasized.Trade Review “The book is of high quality and recommended reading for anyone working with dendrimers or wanting to have a good reference book; rich in information, clearly organized and thoroughly referenced with topical primary publications.” (Angewandte Chemie, 2012) Table of ContentsPreface xv Part 1 Generalities, Syntheses, Characterizations, and Physicochemical Properties 1 1 Syntheses of Dendrimers and Dendrons 3 Anne-Marie Caminade 1.1 Introduction: What Are Dendrimers and Dendrons? 3 1.2 Syntheses of Poly(propyleneimine) Dendrimers (PPI) 5 1.3 Synthesis of Poly(amidoamine) Dendrimers (PAMAM) 5 1.4 Syntheses of Poly(ether) Dendrimers 7 1.5 Syntheses of Poly(ester) Dendrimers 10 1.6 Synthesis of Poly(lysine) Dendrimers 14 1.7 Syntheses of Silicon-Containing Dendrimers 15 1.8 Syntheses of Phosphorus-Containing Dendrimers 16 1.9 Syntheses of Carbon-Based Dendrimers 17 1.10 Syntheses of Dendrimers Constituted of Nitrogen Heterocycles 19 1.11 Syntheses by Self-Assembly 21 1.12 Accelerated Syntheses 26 1.13 Conclusion 30 References 30 2 Methods of Characterization of Dendrimers 35 Anne-Marie Caminade 2.1 Introduction 35 2.2 Spectroscopy and Spectrometry 36 2.2.1 Nuclear Magnetic Resonance (NMR) 36 2.2.2 Mass Spectrometry 40 2.2.3 X-ray Diffraction 41 2.2.4 Infrared (IR) and Raman Spectroscopy 42 2.2.5 Ultraviolet–Visible (UV–vis) Spectroscopy 43 2.2.6 Fluorescence 44 2.2.7 Chirality, Optical Rotation, and Circular Dichroism (CD) 45 2.2.8 Electron Paramagnetic Resonance (EPR) 45 2.2.9 Electrochemistry 46 2.2.10 Magnetometry 46 2.2.11 Mössbauer Spectroscopy 46 2.2.12 X-ray Spectroscopies 47 2.3 Scattering Techniques 47 2.3.1 Laser Light Scattering (LLS) 47 2.3.2 Small-Angle Neutron Scattering (SANS) 47 2.3.3 Small-Angle X-ray Scattering (SAXS) and Wide-Angle X-ray Scattering (WAXS) 48 2.4 Microscopy 48 2.4.1 Transmission Electron Microscopy (TEM) 49 2.4.2 Atomic Force Microscopy (AFM) 49 2.4.3 Polarizing Optical Microscopy (POM) 50 2.5 Rheology and Physical Characterizations 50 2.5.1 Intrinsic Viscosity 50 2.5.2 Differential Scanning Calorimetry (DSC) 50 2.5.3 Dielectric Spectroscopy (DS) 51 2.5.4 Dipole Moments 51 2.6 Separation Techniques 52 2.6.1 Size Exclusion Chromatography 52 2.6.2 Electrophoresis 53 2.7 Conclusion 53 References 54 3 Luminescent Dendrimers 67 Anne-Marie Caminade 3.1 Introduction 67 3.2 Dendrimers with Fluorescent Terminal Groups 68 3.2.1 Fully Substituted Dendrimers 68 3.2.2 Partially Substituted Dendrimers 69 3.3 Luminescent Group at the Core of Dendrimers and Energy/Light-Harvesting Properties 74 3.3.1 Organic Fluorophores as Cores 74 3.3.2 Porphyrins and Phthalocyanines as Cores 77 3.3.3 Metallic Cores 78 3.4 Fluorescent Groups inside the Structure of Dendrimers 79 3.5 Intrinsically Fluorescent Dendrimers 81 3.5.1 Fluorescent Groups throughout the Dendrimeric Structure 81 3.5.2 Fluorescence of Dendrimers without Known Fluorophores 86 3.6 Two-Photon-Excited Fluorescence of Dendrimers 86 3.7 Conclusion 89 References 90 4 Stimuli-Responsive Dendrimers 99 Anne-Marie Caminade 4.1 Introduction 99 4.2 Photoresponsive Dendrimeric Structures 100 4.2.1 Azobenzene-Containing Dendrimers and Dendrons 101 4.2.2 Other Types of Photoresponsive Dendrimers 108 4.3 Thermoresponsive Dendrimeric Structures 110 4.3.1 Thermoresponsive Properties of Dendrimers 110 4.3.2 Thermoresponsive Properties of Dendrons and Dendronized Polymers 112 4.4 Dendrimers Responsive to Solution Media Changes 114 4.4.1 pH-Responsive Dendrimers 114 4.4.2 Dendrimers Disassembly 115 4.5 Conclusion 117 References 118 5 Liquid Crystalline Dendrimers 125 Anne-Marie Caminade 5.1 Introduction 125 5.2 Mesogenic Groups as Terminal Functions of Dendrons 126 5.3 Mesogenic Groups as Terminal Functions of Dendrimers 131 5.4 Mesogenic Groups as Branches of Dendrimers 134 5.5 Conclusion 135 References 136 6 Dendrimers and Nanoparticles 141 Cédric-Olivier Turrin and Anne-Marie Caminade 6.1 Introduction 141 6.2 Dendrimers or Dendrons for Coating Nanoparticles 142 6.2.1 Dendronization of Nanoparticles by Ligand Exchange 142 6.2.2 Direct Synthesis of Dendronized Nanoparticles 147 6.2.3 Dendrimer Coated Nanoparticles 149 6.2.4 Nanocomposites with Interdendrimer Nanoparticles 151 6.3 Dendrimers as Templates for the Synthesis of Dendrimer-Encapsulated Nanoparticles (DENs) 152 6.3.1 Catalysis with Dendrimer-Encapsulated Nanoparticles 153 6.3.2 Other Uses of Dendrimer-Encapsulated Nanoparticles 154 6.4 Conclusion and Perspectives 154 References 155 Part 2 Applications in Catalysis 163 7 Terminal Groups of Dendrimers as Catalysts for Homogeneous Catalysis 165 Armelle Ouali and Anne-Marie Caminade 7.1 General Introduction 165 7.1.1 The “Dendrimer Effect” 165 7.1.2 Recycling the Catalysts 166 7.2 Catalytic Organometallic Sites as Catalysts for Homogeneous Catalysis 167 7.2.1 Formation of C–X Bonds (X = C, N, O) 167 7.2.2 Addition Reactions on a C=X Double Bond (X = C, O) 175 7.2.3 Oxidation Reactions 177 7.3 Organocatalysis with Dendrimers 178 7.4 Conclusion 178 References 179 8 Catalytic Sites inside the Dendrimeric Structure for Homogeneous Catalysis 183 Armelle Ouali and Anne-Marie Caminade 8.1 Introduction 183 8.2 Catalytic Sites as the Core of Dendrimers 184 8.2.1 Dendrimers Bearing a Transition-Metal-Based Complex at the Core 184 8.2.2 Dendrimers Bearing an Organocatalyst at the Core 188 8.3 Catalytic Sites inside the Branches of Dendrimers 191 8.3.1 Formation of C–X Bonds (X = C, N, O) 191 8.3.2 Addition Reactions on a C=C Double Bond: Olefi n Hydrogenation 192 8.4 Conclusion 192 References 193 9 Dendrimers as Homogeneous Enantioselective Catalysts 197 Armelle Ouali and Anne-Marie Caminade 9.1 Introduction 197 9.2 Catalytic Organometallic Sites as Catalysts for Homogeneous Catalysis 198 9.2.1 Formation of C–X Bonds (X = C, N, O) 198 9.2.2 Addition Reactions on a C=X Double Bond (X = C, O) 204 9.3 Organocatalysis with Dendrimers 209 9.3.1 Aldolizations 209 9.3.2 Aza–Morita–Baylis–Hillmann Reactions 209 9.3.3 Transaminations 210 9.4 Conclusion 210 References 210 10 Catalysis with Dendrimers in Particular Media 215 Régis Laurent and Anne-Marie Caminade 10.1 Introduction 215 10.2 Two-Phase (Liquid–Liquid) Media 216 10.3 Catalysis in Ionic Liquids 219 10.4 Catalysis in Supercritical Media 220 10.5 Catalysis in Aqueous Media 221 10.6 Conclusion 234 References 234 11 Heterogeneous Catalysis with Dendrimers 239 Régis Laurent and Anne-Marie Caminade 11.1 Introduction 239 11.2 Catalysis with Dendrons Synthesized from a Solid Material 240 11.2.1 Silica as an Inorganic Support 240 11.2.2 Polymers and Resins as Organic Supports 248 11.3 Catalysis with Dendrons or Dendrimers Grafted on to a Solid Surface 254 11.4 Catalysis with Insoluble Dendrimers 257 11.5 Conclusion 260 References 261 Part 3 Applications for the Elaboration or Modification of Materials 267 12 Dendrimers inside Materials 269 Régis Laurent and Anne-Marie Caminade 12.1 Introduction 269 12.2 Dendrimers for the Elaboration of Gels 270 12.2.1 Dendrimers for the Elaboration of Supramolecular Hygrogels 270 12.2.2 Dendrimers for the Elaboration of Polymer-Type Hygrogels 273 12.2.3 Dendrimers for the Elaboration of Organogels 276 12.3 Dendrimers inside Silica Gels 280 12.4 Dendrimers inside Other Types of Materials 285 12.5 Dendrimers for the Elaboration of OLEDs 288 12.5.1 Fluorescent Dendrimers for the Elaboration of OLEDs 290 12.5.2 Phosphorescent Dendrimers for the Elaboration of OLEDs 295 12.6 Conclusion 298 References 299 13 Self-Assembly of Dendrimers in Layers 313 Béatrice Delavaux-Nicot and Anne-Marie Caminade 13.1 Introduction 313 13.2 Langmuir–Blodgett Films of Dendrons and Dendrimers 314 13.2.1 Poly(benzyl ether) Derivatives 316 13.2.2. Poly(amidoamine) and Poly(propyleneimine) Derivatives 319 13.2.3 Azobenzene Derivatives 320 13.2.4 Poly(carbosilane) Dendrimer Derivatives 321 13.2.5 Fullerene C60 Derivatives 322 13.2.6 Other Examples 325 13.3 Assemblies of Dendrons and Dendrimers on Solid Surfaces 326 13.3.1 Assembly of Dendrons and Dendrimers on Gold Surfaces 327 13.3.2 Assembly of Dendrons and Dendrimers on Silicon Substrates or Related Substrates 330 13.4 Several Routes for the Formation of Dendron or Dendrimer Multilayers 334 13.5 Nanoimprinting with Dendrons and Dendrimers on Solid Surfaces 342 13.5.1 Dendrimer-Based Self-Assembled Monolayers as Resists for Scanning Probe Lithography 342 13.5.2 Microprinting, Transfer Printing, and Dip-Pen Nanolithography with Dendrimers 344 13.6 Conclusion 350 References 351 14 Dendrimers as Chemical Sensors 361 Anne-Marie Caminade 14.1 Introduction 361 14.2 Dendrimers as Chemical Sensors in Solution 362 14.2.1 Porphyrins and Other Macrocyclic Derivatives as the Core or Branches of Dendrimeric Sensors 362 14.2.2 Terminal Groups of Dendrimers as Sensors in Solution 363 14.3 Dendrimers as Electrochemical Sensors 365 14.4 Dendrimers on Modifi ed Surfaces as Chemical Sensors 367 14.4.1 Dendrimers on Surfaces at the Interface with a Solution 367 14.4.2 Dendrimers on Surfaces at the Interface with a Vapor 368 14.5 Conclusion 370 References 370 15 Dendrimers as Biological Sensors 375 Anne-Marie Caminade 15.1 Introduction 375 15.2 Dendrimers as Sensors in Solutions of Biological Media 375 15.3 Detection by Electrochemical Methods 378 15.4 Dendrimers or Dendrons for DNA Microarrays 380 15.5 Dendrimers for Other Types of Biomicroarrays 383 15.6 Dendrimers on Other Types of Support 384 15.7 Dendrimers as Multiply Labeled Entities Connected to the Target 385 15.8 Conclusion 386 References 387 Part 4 Applications in Biology/Medicine 393 16 Dendrimers for Imaging 395 Cédric-Olivier Turrin and Anne-Marie Caminade 16.1 Introduction 395 16.2 Magnetic Resonance Imaging with Dendrimers 395 16.2.1 Paramagnetic Dendrimer-Based Contrast Agents 398 16.2.2 PARACEST Dendrimer-Based Contrast Agents 402 16.2.3 Superparamagnetic Dendrimer-Based Contrast Agents 402 16.2.4 Dendrimer-Based 129Xe HYPER-CEST MRI Contrast Agents 403 16.2.5 19F Dendrimer-Based MRI Contrast Agents 403 16.3 Other Types of Imaging with Dendrimers 403 16.3.1 Dendrimers for Optical Imaging 403 16.3.2 Dendrimers for Nuclear Medicine (NM) Imaging and Computed Tomography X-Ray Imaging (CT) 405 16.4 Conclusion and Perspectives 407 References 407 17 Dendrimers as Transfection Agents 413 Cédric-Olivier Turrin and Anne-Marie Caminade 17.1 Introduction 413 17.2 Gene Transfection with PAMAM Dendrimers 415 17.2.1 Pioneering Results 415 17.2.2 Gene Transfection with Surface-Modifi ed PAMAM 416 17.2.3 Gene Transfection with Core-Modifi ed PAMAM 418 17.2.4 Gene Transfection with PAMAM-Functionalized Nanoparticles 419 17.2.5 Gene Transfection with PAMAM-Like Hyperbranched Polymers 420 17.3 Gene Transfection with Other Dendrimers 421 17.3.1 Gene Transfection with PPI Dendrimers 421 17.3.2 Gene Transfection with Peptide-Based Dendrimers 422 17.3.3 Gene Transfection with Phosphorus-Based Dendrimers 423 17.3.4 Gene Transfection with Silane-Based Dendrimers 424 17.4 Conclusion and Perspective 426 References 426 18 Dendrimer Conjugates for Drug Delivery 437 Cédric-Olivier Turrin and Anne-Marie Caminade 18.1 Introduction 437 18.2 Improving Bioavailability with Dendrimers 438 18.3 Passive Targeting in Tumors with Dendrimer–Drug Conjugates 440 18.3.1 Dendrimer–Drug Bioconjugates and the EPR Effect 440 18.3.2 PEGylated Dendrimeric Scaffolds 442 18.4 Active Targeting with Site-Specifi c Dendrimer–Drug Conjugates 446 18.4.1 Addressing with Folic Acid (FA) 446 18.4.2 Addressing with Tumor-Homing Peptides 448 18.4.3 Addressing with Monoclonal Antibodies 449 18.5 Dendrimers for Photodynamic Therapy (PDT) 449 18.6 Dendrimers for Boron Neutron Capture Therapy (BNCT) 451 18.7 Conclusion and Perspectives 452 References 453 19 Encapsulation of Drugs inside Dendrimers 463 Cédric-Olivier Turrin and Anne-Marie Caminade 19.1 Introduction 463 19.2 From Dendritic Boxes to Dendrimer-Based Formulations 464 19.3 Improving Bioavailability with Dendrimers? 464 19.4 Toxicological Issues 465 19.5 Dendrimer-Based Formulations for Drug Delivery 466 19.5.1 Nontargeted Formulations 466 19.5.2 Supramolecular Assemblies Involving Surface Ionic Interactions 473 19.5.3 Targeted Formulations 475 19.6 Conclusion and Perspectives 477 References 477 20 Unexpected Biological Applications of Dendrimers and Specifi c Multivalency Activities 485 Cédric-Olivier Turrin and Anne-Marie Caminade 20.1 Introduction 485 20.2 Dendrimers and Multivalency 486 20.2.1 Multivalent Effects and Dendrimeric Effects 486 20.2.2 Glycodendrimers 487 20.3 Antimicrobial Dendrimers 488 20.3.1 Polycationic Dendrimers 489 20.3.2 Polyanionic Dendrimers 491 20.4 From Immunomodulation to Regenerative Medicine 494 20.4.1 Immunomodulation and Anti-Inflammation 494 20.4.2 Dendrimers and Regenerative Medicine 498 20.5 Conclusion and Perspectives 501 References 502 21 General Conclusions and Perspectives 511 Anne-Marie Caminade Index 515

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Book SynopsisFrom reviews of previous volumes: Essential for chemistry collections at the university and research levels. --New York Public Library .highly recommended.lots of succinct, practical information on recent developments.in a format that is easy to use. The reagents are taken up in alphabetical order (common usage names, not CAS indexing code names), sometimes several to a page, sometimes several pages to a reagent. One can expect to find how to make the reagent (in loose terms), or where it can be bought, what it is good for, and where to seek complete details.As with previous volumes, one can profit from just browsing, even if one does not feel a need to look up any particular subject. It is thus a secondary function of the book to help one keep abreast of the field, and it would be a rare chemist who would not learn something new and useful from a casual perusal of the pages. --Journal of the American Chemical Society Reagents for Organic Synthesis Volume 1 1967 (0-471-25875-X) 1,475 p

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Book SynopsisPart 1 of a projected sub-series on isoxazoles. It is devoted to mono-nuclear isoxazoles and to their dihydro- and tetrahydro-derivatives. Each chapter represents a survey on physical properties, syntheses and reactions of the three classes of compounds.Table of ContentsIsoxazoles. Isoxazolines (Dihydroisoxazoles). Isoxazolidines (Tetrahydroisoxazoles). References. Index.

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Book SynopsisThe Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.Table of ContentsAminothiazoles and Their Derivatives (R. Barone et al.). Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (C. Roussel et al.). Subject Index.

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Book SynopsisUpdated every five years, the series represents the optimal compromise between currency and a sufficient body of material for cohesive and comprehensive treatment in a monograph. Provides a quick yet thorough overview of the synthetic routines that have been used to access specific classes of therapeutic agents. Materials are organized by chemical class, and syntheses are taken back to available starting materials. Discusses disease state, rational for method of drug therapy, biological activities of each compound and preparation. Coverage also includes those generic pharmaceutical compounds not accorded clinical status. A glossary defines biological terms.Table of ContentsMonocyclic and Acyclic Aliphatic Compounds. Derivatives of Benzyl and Benzhydryl Alcohols and Amines. Phenylethyl and Phenylpropylamines. Arylalkanoic Acids and Their Derivatives. Monocyclic Aromatic Compounds. Steroids. Polycyclic Aromatic and Hydro-aromatic Compounds. Five-Membered Heterocycles. Six-Membered Heterocycles. Morphinoids. Five-Membered Heterocycles Fused to One Benzene Ring. Six-Membered Heterocycles Fused to One Benzene Ring. Benzodiazepines. Heterocycles Fused to Two Benzene Rings. beta-Lactam Antibiotics. Miscellaneous Fused Heterocycles. Indexes. Errata for Volume 1 of Organic Chemistry of Drug Synthesis.

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Book SynopsisThe Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.Table of Contents1. Azwdines 1James A. Deymp 2. Azirines 215Vasu Nair 3. Three-Membered Rings Containing Sulfur 333Uri Zoller Author Index 631 Subject Index 673

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Book SynopsisUpdated every five years, the series represents the optimal compromise between currency and a sufficient body of material for cohesive and comprehensive treatment in a monograph. Provides a quick yet thorough overview of the synthetic routines that have been used to access specific classes of therapeutic agents. Materials are organized by chemical class, and syntheses are taken back to available starting materials. Discusses disease state, rational for method of drug therapy, biological activities of each compound and preparation. Coverage also includes those generic pharmaceutical compounds not accorded clinical status. A glossary defines biological terms.Table of ContentsAlicyclic and Cyclic Compounds. Phenethyl and Phenoxypropanolamines. Arylaliphatic Compounds. Monocyclic Aromatic Agents. Polycyclic Aromatic Compounds. Steroids. Compounds Related to Morphine. Five-Membered Heterocycles. Six-Membered Heterocycles. Five-Membered Heterocycles Fused to Benzene. Benzofused Six-Membered Heterocycles. Beta Lactams. Miscellaneous Fused Heterocycles. Indexes.

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Book SynopsisThis annual series continues the cooperative effort to abstract and publish in formula order all the ultraviolet-visible spectra of organic compounds presented in the journal literature. Over 50 chemists have searched 100 plus titles during the course of this project to assemble over 350,000 spectra throughout these volumes.

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Book SynopsisThis is a detailed description of the general principles and strategies used to solve problems concerning the chemical synthesis of complex organic molecules.Table of ContentsGENERAL APPROACHES TO THE ANALYSIS OF COMPLEX SYNTHETIC PROBLEMS. The Basis for Retrosynthetic Analysis. Transform-Based Strategies. Structure-Based and Topological Strategies. Stereochemical Strategies. Functional Group-Based and Other Strategies. Concurrent Use of Several Strategies. SPECIFIC PATHWAYS FOR THE SYNTHESIS OF COMPLEX MOLECULES. Macrocyclic Structures. Heterocyclic Structures. Sesquiterpenoids. Polycyclic Isoprenoids. Prostanoids. Leukotrienes and Other Bioactive Polyenes. GUIDE TO THE ORIGINAL LITERATURE OF MULTISTEP SYNTHESIS. Index.

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Book SynopsisDiscover the exciting, promising field of molecular level artificial photosynthesis This special volume of Progress in Inorganic Chemistry presents the theory and practice of molecular artificial photosynthesis-a field holding tremendous promise now that molecular solar energy materials are fast becoming competitive with their solid-state counterparts. The only book on the market to address this important area of inorganic research, Molecular Level Artificial Photosynthetic Materials shows us, in effect, how to imitate the complex natural processes of photosynthesis-featuring state-of-the-art strategies and techniques for creating artificial photosynthetic devices at the molecular level. It takes a multidisciplinary approach, drawing on materials science techniques used in the design of solar energy devices, examining the molecular nature of the chemistry involved, and applying existing knowledge in inorganic photochemistry and photophysics to the growing pool of moleTable of ContentsA Supramolecular Approach to Light Harvesting and Sensitization of Wide-Bandgap Semiconductors: Antenna Effects and Charge Separation (C. Bignozzi, et al.). Langmuir-Blodgett Films of Transition Metal Complexes (M DeArmond & G. Fried). Layered Metal Phosphonates as Potential Materials for the Design and Construction of Molecular Photosynthetic Systems (L. Vermeulen). Light-Induced Processes in Molecular Gel Materials (F. Castellano & G. Meyer). Charge-Transfer Processes in Zeolites: Toward Better Artificial Photosynthetic Models (P. Dutta & M. Ledney). Native and Surface Modified Semiconductor Nanoclusters (P. Kamat). Molecular and Supramolecular Surface Modification of Nanocrystalline TiO_2 Films: Charge-Seperating and Charge-Injecting Devices (T. Gerfin, et al.). Indexes.

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Book SynopsisThe volumes in this continuing series provide a compilation of current techniques and ideas in inorganic synthetic chemistry. Includes inorganic polymer syntheses and preperation of important inorganic solidsd, sutheses used in the development of pharamacologically active inorganic compounds, small-molecule coordination complexes, and related compounds. Also contains calcuable information on transition organometallic compunds, including species with meta-metal cluster molecules. All syntheses presented here have been tested.Table of ContentsChapter One MAIN GROUP COMPOUNDS. 1. Volatile-² Diketonate Complexes of Calcium(II), Strontium(II), and Barium(II). 2. Bis(1,1,1,3,3,3-hexamethyldisilazanato) bis(tetrahydrofuran)-barium. 3. Ammonium and Barium Salts of the Tris- [1,2-benzenediolate(2-)-O,O']titanium(IV) Dianion. 4. N-Donor Adducts of Dimethylzinc. 5. Arene Chalcogenolato Complexes of Zinc and Cadmium. 6. Arene Thiolato, Selenolato, and Tellurolato Complexes of Mercury. 7. Electronic Grade Alkyls of Group 12 and 13 Elements. 8. Trimethylindium and Trimethylgallium. 9. (N,N-dimethylethanamine) trihydridoafuminum. 10. Tertiary Amine and Phosphine Adducts of Gallium Trihydride. 11. trans-1,1-Di-tert-butyl-2,3-dimethylsilane and 2,2-Di-tert-butyl 1,1,1-triethyldisilane. 12. Tin(II) Sulfide and Tin(II) Selenide. 13. Tin(IV) Fluoride (Tetrafluorostannane). 14. N,N,N'-Tris(trimethylsilyl) Amidines. 15. Homoleptic Bismuth Amides. 16. Cyclo-tetrasulfur(2+) Bis[hexafluoroarsenate(1-)], Cyclo-tetrasulfur(2+)Bis[undecafluorodiantimonate(1-)], Cyclo-tetraselenium(2+)Bis[hexafluroarsenate(1-)] and Cyclo-tetraselenium(2+) Bis[undecafluorodiantimonate(1-)]. 17. Fe2(S2)(CO)6, and Fe3Te2(CO)9,10. Chapter Two LIGANDS AND REAGENTS. 18. 5,10,15,20-Tetrakis (2,6-dihydroxyphenyl) -21H,23H-porphine. 19. Tribenzocycline (TBC) and Tetrabenzocyclyne (QBC). 20. (Chloromethylene)bis[trimethylsilane] [Bis(trimethylsilyl)chloromethane]. 21. S,S-Chiraphos [(S,S)-(-)-(1,2-Dimethyl-1,2-ethandiyl) bis-(diphenylphosphine)]. 22. ²-Ketophosphines: Ligands of Catalytic Relevance. 23. N,N-Diisobutyl-2-(octylphenylphosphinyl) acetamide (CMPO). 24. Aresenic(III) Chloride. 25. Tris(trimethylsilyl)arsine and Lithium Bis(trimethylsilyl)arsenide. 26. Sterically Hindered Arene Chalcogenols. 27. Tris(trimethylsilyl)silyl Lithium Tris(tetrahydrofuran), Lithium Tris(trimethylsilyl)silyltellurolate Bis(tetrahydrofuran), and Tris(trimethylsilyl)silyltellurol. 28. Metal Complexes of the Lacunary Heteropolytungstates [B-±-PW9O34]9- and [±-P2W15O56]12-. 29. Polyoxoanion-Supported, Atomically Dispersed Iridium(I) and Rhodium(I). Chapter Three ORGANOMETALLIC COMPOUNDS. 30. One-Pot Synthesis of Dicarbonyltris(phosphine)iron(0) Complexes from Pentacarbonyliron. 31. Tricarbonylbis(phosphine)iron(0) Complexes. 32. (·5-Pentamethylcyclopentadienyl) (·5-cyclopentadienyl)iron [1,2,3,4,5-pentamethylferrocene]. 33. Pyrazolate-Bridged Ruthenium(I) Carbonyl Complexes. 34. Main Group-Transition Metal Carbonyl Complexes. 35. MnII4(1/44-O)[(CO)9Co3(1/43-CCO2)]6, M = Co, Zn. 36. 1,2,3,4-Tetramethyl-5-(trifluoromethyl)cyclopentadiene (Cp+ H) and Di-1/4-Chlorodichlorobis [·5-tetramethyl- (Trifluoromethyl)Cyclopentadienyl] Dirhodium(III). 37. Acetonitrile-Substituted Derivatives of Rh6(CO)16: Rh6(CO)16-x(NCMe)x(x = 1, 2). 38. Tetraphenylarsonium Carbonyltrichloroplatinate(II). Chapter Four TRANSITION METAL, LANTHANIDE, AND ACTINIDE COMPLEXES. 39. Dichlordioxobis(dimethyl sulphoxide)molybdenum(VI). 40. Metal-Catalyzed Synthesis of cis-[Re(CO)4,LI] [L = P(OMe)3, PMe2Ph, PPh3]. 41. Tris(l,2-bis(dimethylphosphino) ethane)rhenium(1) Trifluoromethanesulfonate, [Re(DMPE)3[CF3SO3]. 42. Tetrahalo Oxorhenate Anions. 43. A Rhenium(I) Dinitrogen Complex Containing a Tertiary Phosphine. 44. Bis(2,4-pentanedionato)iron(II) [Iron(II)Bis(acetylacetonate)]. 45. Synthesis of trans-Tetraammined.ichlorocobalt(III)Chloride. 46. [[3,3'-(1,3-Propanediyldiimino) bis[3-methy-2-butanone]- dioximatel(1-)-N,N',N'',N''']nickel(II), Nioyl. 47. Platinum Complexes Suitable as Precursors for Synthesis in Nonaqueous Solvents. 48. Tetrakis(propanenitrile)platinum(II)Trifluoromethanesulfonate as a Suitable Intermediate in Synthetic Pt(II) Chemistry. 49. [(1,2,5,6-·)-1,5-Cyclooctadiene]dimethylplatinum(II). 50. Bis(2,2,6,6-tetramethyl-3,5 -heptanedionato)copper. 51. Lewis Base Adducts of 1,1,1,5,5,5 -Hexafluoro-2,4-pentadionato -Copper(I) Compounds. 52. Copper(II) Alkoxides. 53. Pyrazolato Copper(I) Complexes. 54. Tris(2,2,6,6-tetramethyl -3,5-heptanedionato) Yttrium. 55. Lewis Base Adducts of Uranium Triiodide and Tris[bis(trimethylsilyl)amido] uranium. Contributor Index. Subject Index. Formula Index. Chemical Abstracts Service Registry Number Index.

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Book SynopsisVolume 75 of the Organic Synthesis series contains 29 carefully checked and edited experimental procedures describing leading-edge synthetic methods, important reagents, and useful building blocks.Table of ContentsPartial table of contents: Catalytic Asymmetric Allylation Reactions:(S)-1-Phenylmethoxy)-4-Penten-2-OL (G. Keck & D.Krishnamurthy). Ethyl (R)-2-Azidopropionate (A. Thompson, et al.). (4R,5S)-4,5-Diphenyl-3-Vinyl-2-Oxazolidinone (T. Akiba, etal.). 3-Chloro-2-(Chloromethyl)-1-Propene (K. Lynch & W.Dailey) [1.1.1]Propellane (K. Lynch & W. Dailey). N-Benzyl-2,3-Azetidinedione (C. Behrens & L. Paquette). Preparation of Cyanoalkynes: 3-Phenyl-2-Propynenitrile (F.-T. Luo,et al.). 2-Trimethylsilylethane-Sulfonyl Chloride (SES-Cl) (S. Weinreb, etal.). 4-Dimethylamino-N-Triphenyl-Methylpyridinium Chloride (A. Bhatia,et al.). 6,7-Dihydrocyclopenta-1,3-Dioxin-5(4H)-One (K. Chen, et al.). 3-Cyclopentene-1-Carboxylic Acid (J.-P. Depres & A.Greene). Unchecked Procedures. Indexes.

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Book SynopsisThis volume provides a non-mathematical introduction to electronic excitation in organic molecules and their spectroscopy, photophysics, and photochemistry. Simple qualitative models, such as the perimeter model, are used to describe the nature of electronic states, and this book reveals how these states are probed by spectroscopy with ordinary and polarized light, including natural and magnetic circular dichroism. The concept of potential energy surfaces is emphasized in discussing the photophysical processes and photochemical reactions that follow excitation. Particular attention is paid to the behavior of molecules at biradicaloid geometries and spin-orbit coupling in biradicals. Simple intuitive models for electronic structure and reactivity are emphasized, and practical application of theory is illustrated through numerous worked examples.Table of ContentsFrom the Contents: Spectroscopy in the Visible and UV Region/ Absorption Spectra of Organic Molecules/ Optical Activity/ Principles of the Quantum Chemical Description of Photophysical and Photochemical Processes/ Photophysical Processes/ Photochemical Reaction Models/ Organic Photochemistry

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Book SynopsisMost books on organic conformational deal with sterochemistry, while neglecting the spatial structure of organic molecules, especially the unusual ones. This ambitious monograph presents a global view of organic structure and conformational analysis in a very readable style. The author''s fascination with the beauty and variety of shapes of organic molecules comes through in her description of the importance of molecular organization in organic chemical and biological systems, the quantum foundations of molecular spatial structure, molecular symmetry, chiralty and physical methods for studying molecular geometry. She provides ample bases for the new trends in organic conformational chemistry, including the application of Computer Assisted Molecular Design (CAMD) to organic synthesis.Table of ContentsMolecular Symmetry. Chirality and its Importance in Nature: Cahn, Ingold, and Prelog Classification of Chirality and its Modification. Quantum Chemistry and Molecular Mechanics: Theoretical Foundation of Molecule Spatial Structure. Physical Methods as a Source of Information on the Values of Bond Lengths and Angles in Organic Molecules. Nonstandard Systems, the Purposes of Studying Them, Mutual Interaction Between Theory and Synthetic Chemistry. Molecular Modeling: Computer Assisted Molecular Design (CAMD). Index.

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Book SynopsisIntroduction to Theoretical Organic Chemistry provides an introduction for chemists with a limited mathematical background, yet need a working understanding of quantum chemistry as applied to problems in organic chemistry. This book is unique in that it is written at the level of the advanced undergraduate or beginning graduate student in organic chemistry, whose exposure to theoretical chemistry is relatively recent. It fills a niche in that most books on theoretical organic chemistry are written by theoretical or computational chemists, whereas this book is written by an organic chemist. The book covers molecular modeling computer software, and offers a useful guide to the scope and limitations of each program, along with specific examples of input and output for several of the most popular software. Numerous examples and exercises are provided.Table of ContentsThe Hydrogen Atom and the Hydrogen Molecule. Hückel Molecular Orbital Theory. The PMO Method. Aromaticity, Antiaromaticity and Resonance. Chemical Reactivity via Hückel Theory. Pericyclic Reactions, Orbital Symmetry, PMO and Frontier MO Theories. Improvements on the Hückel Theory. Molecular Modelling-Molecular Mechanics. Molecular Modeling-Semiemprirical Methods. Molecular Modelling-AB initio Methods and Density Functional Theory. Molecular Modelling-NMR Spectroscopy and Moelcular Structure.

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Book SynopsisThis second volume of the series ''Reviews in Computational Chemistry'' explores new applications, new methodologies, and new perspectives. The topics covered include conformational analysis, protein folding, force field parameterizations, hydrogen bonding, charge distributions, electrostatic potentials, electronic spectroscopy, molecular property correlations, and the computational chemistry literature. Methodologies described include conformational search strategies, distance geometry, molecular mechanics, molecular dynamics, ab initio and semiempirical molecular orbital calculations, and quantitative structure-activity relationships (QSAR) using topological and electronic descriptors. A compendium of molecular modeling software will help users select the computational tools they need. Each chapter in ''Reviews in Computational Chemistry'' serves as a brief tutorial for organic, physical, pharmaceutical, and biological chemists new to the field. Practitioners will be intereTable of ContentsA Survey of Methods for Searching thr Conformational Space of Small and Medium-Sized Molecules (A. Leach). Simplified Models for Understanding and Predicting Protein Structure (J. Troyer and F. Cohen). Moleculaar Mechanics: The Art and Science of Parameterization (J. Bowen and N. Allinger). New Approaches to Empirical Force Fields (U. Dinur and A. Hagler). Calculating the Properties of Hydrogen Bonds by ab Initio Methods (S. Scheiner). Net Atomic Charge and Multiple Models for the ab Initio Molecular Electric Potential (D. Williams). Molecular Electrostatic Potentials and Chemical Reactivity (P. Politzer and J. Murray). Semiempirical Molecular Orbital Methods (M. Zerner). The Molecular Connectivity Chi Indexes and Kappa Shape Indexes in Structure-Property Modeling (L. Hall and L. Kier). The Electron-Topological Approach to the QSAR Problem (I. Bersuker and A. Dimoglo). The Computational Chemistry Literature (D. Boyd). Appendix: Compendium of Software for Molecular Modeling (D. Boyd). Author Index. Subject Index.

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Book SynopsisThis work offers a comprehensive, up-to-date account of 30 years of thermochemical investigations and findings from around the world.Table of ContentsFrom the Contents: Bomb Calorimeters/ Temperature Measurements in Calorimetry/ Calorimetric Part of Thermochemical Experiments/ Chemical Part of Thermochemical Experiment/ Calorimetry of Combustion 1/m Dissolution/ Calculations for Thermochemical Experiments/ Purification and Determination of Studied Substance Purity/ Experimental Data on Evaporation Enthalpy and Organic Substance Vapour Pressures/ Geometry, Classification and Enumeration of Isomers/ Relation Between Structures and Properties of Organic Compounds/ Statistical Regularities in Thermodynamic Properties of Isomers and Their Equilibrium Relations/ Complex Chemical Equilibria and Calculation of Equilibrium Compostition of Multicomponent Isomeric Mixtures

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Book SynopsisThis volume provides the sole comprehensive, current reference on the synthetic chemistry of oxazoles. Applications to the syntheses of natural products and other chiral compounds are described.Trade Review"The text is well written and understandable...should be a valuable reference for organic chemists." (Journal of the American Chemical Society, Nov 17, 2004)Table of ContentsContents - Part A. Abbreviations. 5. 2(3H)-Oxazolones and 2(5H)-Oxazolones (T. Kunieda and H. Matsunaga). 6. 4(5H)-Oxazolones (D.C. Palmer). 7. 5(2H)-Oxazolones and 5(4H)-Oxazolones (C. Cativiela and M.D. Diaz-De-Villegas). 8. 2-Oxazolines (G.S.K. Wong and W. Wu). 9. Chiral Bis(oxazolines) (A. Ghosh, G. Bilcer, and S. Fidanze). Author Index. Subject Index.

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Book SynopsisThe well respected and ever popular Fieser and Fieser series on reagents for organic synthesis provides concise descriptions, good structural formulas and selected examples of applications. Provides references to new reagents as well as to reagents included in previous volumes Thousands of entries abstract the most important information on commonly used and new reagents, including preparation, uses, sources of supply, critical comments, references and more Reagents are considered in alphabetical order by common usage names. Table of ContentsIntroduction. Reagents (A to Z). Suppliers. Index of Apparatus. Index of Reagents According to Types. Author Index. Subject Index.

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Book SynopsisDeals with the fundamental chemistry of fully saturated and unsaturated 4-, 5- and 6- membered heterocycles. This title introduces a selection of important heterocyclic compounds and the vital role that they play in life, medicine and industry.Trade Review"Although primarily an undergraduate text, the main principles that govern heterocyclic chemistry as a whole are addressed in this book, providing a sure foundation for those wishing to widen their interest in heterocyclic chemistry in later years." (The Chemist, Summer 2003) "...this is a useful and straightforward little text that could be recommended to students who seriously want to get to grips with the basics of heterocyclic chemistry." (Biochemistry and Molecular Education, Jan/Feb 2002)Table of ContentsIntroduction to Heterocyclic Chemistry. Pyridine. Benzopyridines. Pyrylium Salts, Pyrans and Pyrones. Benzopyrylium Salts, Coumarins, Chromones, Flavonoids and Related Compounds. Five-membered Heterocycles containing One Heteroatom: Pyrrole, Furan and Thiophene. Benzo[b]pyrrole, Benzo[b]furan and Benzo[b]thiophene. Four-membered Heterocycles containing a Single Nitrogen, Oxygen or Sulfur Atom. Answers to Problems. Subject Index.

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Book SynopsisPolycyclic aromatic hydrocarbons (PAHs) were one of the first chemicals discovered to cause cancer in humans. This work covers polycyclic aromatic hydrocarbons with larger than seven rings. It has chapters devoted to sample handling and preparation and methodology.Trade Review"...explains methods for analyzing chemical compounds with aromatic cores..." (SciTech Book News, March 2001)Table of ContentsThe Large PAHs. Ultraviolet/Visible Absorption Spectroscopy. Fluorescence Spectroscopy. Infrared Spectroscopy of LPAHs. Mass Spectrometry. Astrophysical Spectroscopy. Chromatography. LPAH Occurrence. Analytical Techniques for Structure Elucidation. Sample Preparation. Comparison of Methodologies. Appendix. Index.

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Book SynopsisThe Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.Table of ContentsPart One I. Part A. Properties and Resctions of Pyridmes 1R. A. Abramovitch and G. M. Singer Part B. Partially Reduced Pyridines 137Robert E. Lyle II. Synthetic and Natural Sources of the Pyridine Ring 183N. Sboodman, J. O. Hawthorne, P. X. Masciantonio, and A. W. Simon III. Quaternary pyridinium Compounds 309Oscar R. Rodig Index 431

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Book SynopsisHeterogeneous catalytic hydrogenation is the process of conducting a chemical reaction with hydrogen utilizing a catalyst that exists in a different physical phase than the reactants. Catalytic hydrogenation reactions are employed in synthetic organic laboratories and industries as a means for reducing or transforming organic compounds.Trade Review"Chemists will find this a useful guide and it should be in all organic chemistry libraries." (Organic Process Research & Development Journal) "...this book is easy to use to find information quickly...it adds to a useful armoury for dealing with most queries...it is therefore good value..." (Platinum Metals Review, Vol. 46, No. 2, April 2002) "this book is easy to use to find information quickly" (Platinum Metals Review, April 2002) "...a welcome and valuable day-to-day manual..." (Synthesis, No.9, 2002)Table of ContentsPreface. Hydrogenation Catalysts. Reactors and Reaction Conditions. Hydrogenation of Alkenes. Hydrogenation of Alkynes. Hydrogenation of Aldehydes and Ketones. Preparation of Amines by Reductive Alkylation. Hydrogenation of Nitriles. Hydrogenation of Imines, Oximes, and Related Compounds. Hydrogenation of Nitro, Nitroso, and Related Compounds. Hydrogenation of Carboxylic Acids, Esters, and Related Compounds. Hydrogenation of Aromatic Compounds. Hydrogenation of Heterocyclic Aromatic Compounds. Hydrogenolysis. General Bibliography. Author Index. Subject Index.

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Book SynopsisTHIS VOLUME, LIKE THOSE PRIOR TO IT, FEATURES CHAPTERS BY EXPERTS IN VARIOUS FIELDS OF COMPUTATIONAL CHEMISTRY. TOPICS COVERED IN VOLUME 20 INCLUDE VALENCE THEORY, ITS HISTORY, FUNDAMENTALS, AND APPLICATIONS; MODELING OF SPIN-FORBIDDEN REACTIONS; CALCULATION OF THE ELECTRONIC SPECTRA OF LARGE MOLECULES; SIMULATING CHEMICAL WAVES AND PATTERNS; FUZZY SOFT-COMPUTING METHODS AND THEIR APPLICATIONS IN CHEMISTRY; AND DEVELOPMENT OF COMPUTATIONAL MODELS FOR ENZYMES, TRANSPORTERS, CHANNELS, AND RECEPTORS RELEVANT TO ADME/TOX. FROM REVIEWS OF THE SERIES Reviews in Computational Chemistry remains the most valuable reference to methods and techniques in computational chemistry. -JOURNAL OF MOLECULAR GRAPHICS AND MODELING One cannot generally do better than to try to find an appropriate article in the highly successful Reviews in Computational Chemistry. The basic philosophy of the editors seems to be to help the authors produce chapters that are complete, accurate, clear, Trade Review“The editors have done an excellent job and the book is a must on every book shelf of computational chemistry literature.” (ChemPhysChem, 2005; Vol. 6; 7) "…this volume continues the traditions and standards of this series as a prime resource for anyone with an interest in theoretical and computational chemistry…a welcome addition to any library collection." (Journal of the American Chemical Society, March 9, 2005)Table of Contents1. Valence Bond Theory, Its History, Fundamentals, and Applications: A Primer (Sason Shaik and Philippe C. Hiberty). Introduction. A Story of Valence Bond Theory, Its Rivalry with Molecular Orbital Theory, Its Demise, and Eventual Resurgence. Roots of VB Theory. Origins of MO Theory and the Roots of VB–MO Rivalry. The ‘‘Dance’’ of Two Theories: One Is Up, the Other Is Down. Are the Failures of VB Theory Real Ones? Modern VB Theory: VB Theory Is Coming of Age. Basic VB Theory. Writing and Representing VB Wave Functions. The Relationship between MO and VB Wave Functions. Formalism Using the Exact Hamiltonian. Qualitative VB Theory. Some Simple Formulas for Elementary Interactions. Insights of Qualitative VB Theory. Are the ‘‘Failures’’ of VB Theory Real? Can VB Theory Bring New Insight into Chemical Bonding? VB Diagrams for Chemical Reactivity. VBSCD: A General Model for Electronic Delocalization and Its Comparison with the Pseudo-Jahn–Teller Model. What Is the Driving Force, s or p, Responsible for the D6h Geometry of Benzene? VBSCD: The Twin-State Concept and Its Link to Photochemical Reactivity. The Spin Hamiltonian VB Theory. Theory. Applications. Ab Initio VB Methods. Orbital-Optimized Single-Configuration Methods. Orbital-Optimized Multiconfiguration VB Methods. Prospective. Appendix. A.1 Expansion of MO Determinants in Terms of AO Determinants. A.2 Guidelines for VB Mixing. A.3 Computing Mono-Determinantal VB Wave Functions with Standard Ab Initio Programs. Acknowledgments. References. 2. Modeling of Spin-Forbidden Reactions (Nikita Matsunaga and Shiro Koseki). Overview of Reactions Requiring Two States. Spin-Forbidden Reaction, Intersystem Crossing. Spin–Orbit Coupling as a Mechanism for Spin-Forbidden Reaction. General Considerations. Atomic Spin–Orbit Coupling. Molecular Spin–Orbit Coupling. Crossing Probability. Fermi Golden Rule. Landau–Zener Semiclassical Approximation. Methodologies for Obtaining Spin–Orbit Matrix Elements. Electron Spin in Nonrelativistic Quantum Mechanics. Klein–Gordon Equation. Dirac Equation. Foldy–Wouthuysen Transformation. Breit–Pauli Hamiltonian. Zeff Method. Effective Core Potential-Based Method. Model Core Potential-Based Method. Douglas–Kroll Transformation. Potential Energy Surfaces. Minimum Energy Crossing-Point Location. Available Programs for Modeling Spin-Forbidden Reactions. Applications to Spin-Forbidden Reactions. Diatomic Molecules. Polyatomic Molecules. Phenyl Cation. Norborene. Conjugated Polymers. CH(2II) + N2 -- HCN + N(4S). Molecular Properties. Dynamical Aspects. Other Reactions. Biological Chemistry. Concluding Remarks. Acknowledgments. References. 3. Calculation of the Electronic Spectra of Large Molecules (Stefan Grimme). Introduction. Types of Electronic Spectra. Types of Excited States. Theory. Excitation Energies. Transition Moments. Vibrational Structure. Quantum Chemical Methods. Case Studies. Vertical Absorption Spectra. Circular Dichroism. Vibrational Structure. Summary and Outlook. Acknowledgments. References. 4. Simulating Chemical Waves and Patterns (Raymond Kapral). Introduction. Reaction–Diffusion Systems. Cellular Automata. Coupled Map Lattices. Mesoscopic Models. Summary. References. 5. Fuzzy Soft-Computing Methods and Their Applicationsin Chemistry (Costel Saˆrbu and Horia F. Pop). Introduction. Methods for Exploratory Data Analysis. Visualization of High-Dimensional Data. Clustering Methods. Projection Methods. Linear Projection Methods. Nonlinear Projection Methods. Artificial Neural Networks. Perceptron. Multilayer Nets: Backpropagation. Associative Memories: Hopfield Net. Self-Organizing Map. Properties. Mathematical Characterization. Relation between SOM and MDS. Multiple Views of the SOM. Other Architectures. Evolutionary Algorithms. Genetic Algorithms. Canonical GA. Evolution Strategies. Evolutionary Programming. Fuzzy Sets and Fuzzy Logic. Fuzzy Sets. Fuzzy Logic. Fuzzy Clustering. Fuzzy Regression. Fuzzy Principal Component Analysis (FPCA). Fuzzy PCA (Optimizing the First Component). Fuzzy PCA (Nonorthogonal Procedure). Fuzzy PCA (Orthogonal). Fuzzy Expert Systems (Fuzzy Controllers). Hybrid Systems. Combinations of Fuzzy Systems and Neutral Networks. Fuzzy Genetic Algorithms. Neuro-Genetic Systems. Fuzzy Characterization and Classification of the Chemical Elements and Their Properties. Hierarchical Fuzzy Classification of Chemical Elements Based on Ten Physical Properties. Hierarchical Fuzzy Classification of Chemical Elements Based on Ten Physical, Chemical, and Structural Properties. Fuzzy Hierarchical Cross-Classification of Chemical Elements Based on Ten Physical Properties. Fuzzy Hierarchical Characteristics Clustering. Fuzzy Horizontal Characteristics Clustering. Characterization and Classification of Lanthanides and Their Properties by PCA and FPCA. Properties of Lanthanides Considered in This Study. Classical PCA. Fuzzy PCA. Miscellaneous Applications of FPCA. Fuzzy Modeling of Environmental, SAR and QSAR Data. Spectral Library Search and Spectra Interpretation. Fuzzy Calibration of Analytical Methods and Fuzzy Robust Estimation of Location and Spread. Application of Fuzzy Neural Networks Systems in Chemistry. Applications of Fuzzy Sets Theory and Fuzzy Logic in Theoretical Chemistry. Conclusions and Remarks. References. 6. Development of Computational Models for Enzymes, Transporters, Channels, and Receptors Relevant to ADME/Tox (Sean Ekins and Peter W. Swaan). Introduction. ADME/Tox Modeling: An Expansive Vision. The Concerted Actions of Transport and Metabolism. Metabolism. Transporters. Approaches to Modeling Enzymes, Transporters, Channels, and Receptors. Classical QSAR. Pharmacophore Models. Homology Modeling. Transporter Modeling. Applications of Transporters. The Human Small Peptide Transporter, hPEPT1. The Apical Sodium-Dependent Bile Acid Transporter. P-Glycoprotein. Vitamin Transporters. Organic Cation Transporter. Organic AnionTransporters. Nucleoside Transporter. Breast Cancer Resistance Protein. Sodium Taurocholate Transporting Polypeptide. Enzymes. Cytochrome P450. Epoxide Hydrolase. Monoamine Oxidase. Flavin-Containing Monooxygenase. Sulfotransferases. Glucuronosyltransferases. Glutathione S-transferases. Channels. Human Ether-a-gogo Related Gene. Receptors. Pregnane X-Receptor. Constitutive Androstane Receptor. Future Developments. Acknowledgments. Abbreviations. References. Author Index. Subject Index.

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Book SynopsisUpdated every five years, the series represents the optimal compromise between currency and a sufficient body of material for cohesive and comprehensive treatment in a monograph. Provides a quick yet thorough overview of the synthetic routines that have been used to access specific classes of therapeutic agents. Materials are organized by chemical class, and syntheses are taken back to available starting materials. Discusses disease state, rational for method of drug therapy, biological activities of each compound and preparation. Coverage also includes those generic pharmaceutical compounds not accorded clinical status. A glossary defines biological terms.Table of ContentsA Case Study in Molecular Manipulation: The LocalAnesthetics. Monocyclic Alicyclic Compounds. Benzyl and Benzhydryl Derivatives. Penethyl and Phenylpropylamines. Arylacetic and Arylpropionic Acids. Arylethylenes and Their Reduction Products. Monocyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Steroids. Tetracyclines. Acyclic Compounds. Five-Membered Heterocycles. Six-Membered Heterocycles. Derivatives of Morphine, Morphinan, and Benzomorphan; 4-Phenylpiperidines. Five-Membered Heterocycles Fused to One Benzene Ring. Six-Membered Heterocycles Fused to One Benzene Ring. Benzodiazepines. Phenothiazines. Additional Heterocycles Fused to Two Benzene Rings. beta-Lactam Antibiotics. Miscellaneous Fused Heterocycles. Cross Index of Drugs. Glossary. Index.

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Book SynopsisThe Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.Table of ContentsVinylthiophenes and Thienylacetylenes (S. Gronowitz &A.-B. Hornfeldt). Organometallic Derivatives of Thiophenes (T. Frejd). Syntheses, Reactions, and Physical Properties of Bithienyls andPolythienyls and Closely Related Compounds (R. H?kansson). Index.

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Book SynopsisA riveting look at the science, technology and people involved in overcoming early impracticalities of the fledgling chemical vapor deposition (CVD) synthesis method and its development in today''s state of commercial readiness. Provides insights into numerous vapor phase techniques. Surveys the synthesis, structure, properties and applications of diamondlike carbon. Details current and rapidly emerging applications, manufacturing and markets.Table of ContentsPartial table of contents: The Vision of Diamond as an Engineered Material (M. Yoder). Summary of Research on Diamond Growth from the Gas Phase in Russia(D. Fedoseev). Development and Status of Diamondlike Carbon (A. Grill & B.Meyerson). Vapor Phase Diagnostics in Diamond CVD (H. Thorsheim & J.Butler). Physical, Chemical, and Microstructural Characterization andProperties of Diamond (W. van Enckevort). Optical Properties and Optoelectronic Applications of Diamond (J.Pankove & C.-H. Qiu). Industrial Applications of Single-Crystal Diamond (M. Seal). A Comparative Assessment of CVD Diamond Manufacturing Technologyand Economics (J. Busch & J. Dismukes). Index.

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Book SynopsisA reference text focusing on basic organic chemistry and reactions of naturally occurring organic substances in soils. Covers pools of organic matter in soils, transformations, methods of extraction and fractionation. Section two deals primarily with the chemistry of known classes of organic compounds in soils including saccharides, lipids and constituents containing nitrogen, phosphorus and sulfur. Section three is concerned with basic organic chemistry of humic substances, followed by the importance of organic matter associations and interactions. Contains new chapters on NMR spectroscopy, analytical pyrolysis and on chemical structures.Table of ContentsPartial table of contents: Organic Matter in Soils: Pools, Distribution, Transformations, andFunction. Extraction, Fractionation, and General Chemical Composition of SoilOrganic Matter. Organic Forms of Soil Nitrogen. Native Fixed Ammonium and Chemical Reactions of Organic Matter withAmmonia and Nitrite. Organic Phosphorus and Sulfur Compounds. Soil Carbohydrates. Soil Lipids. Biochemistry of the Formation of Humic Substances. Reactive Functional Groups. Structural Components of Humic and Fulvic Acids as Revealed byDegradation Methods. Characterization of Soil Organic Matter by NMR Spectroscopy andAnalytical Pyrolysis. Structural Basis of Humic Substances. Spectroscopic Approaches. Colloidal Properties of Humic Substances. Electrochemical and Ion-Exchange Properties of HumicSubstances. Organic Matter Reactions Involving Pesticides in Soil. Index.

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Book SynopsisProvides synthetic chemists with a method for rapid retrieval of information from the literature, listing material by reaction type rather than by author name or publication date. Each updated volume presents the latest synthetic methods for preparation of monofunctional and difunctional compounds. The organization is logical and easy to follow; sections are arranged according to the possible interconversions between the major functional groups. Enables synthetic chemists to keep abreast of recent developments and retrieve a specific piece of information quickly and easily.Table of ContentsPreparation of Alkynes. Preparation of Acid Derivatives and Anhydrides. Preparation of Alcohols. Preparation of Aldehydes. Preparation of Alkyls, Methylenes and Aryls. Preparation of Amides. Preparation of Amines. Preparation of Esters. Preparation of Ethers, Epoxides and Thioethers. Preparation of Halides and Sulfonates. Preparation of Hydrides. Preparation of Ketones. Preparation of Nitriles. Preparation of Alkenes. Preparation of Oxides. Preparation of Difunctional Compounds. Author Index.

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Book SynopsisReagents for Organic Synthesis This widely respected reference has been brought up to date with the publication of Volume 13. Thousands of entries abstract the most important information on commonly used reagents from 1966 through mid-1986. Every reagent discussed includes the preparation, uses, sources of supply, critical comments, references, and more. Volume 1, 1967, 1,475 pp.Volume 2, 1969, 538 pp.Volume 3, 1972, 401 pp.Volume 4, 1974, 660 pp.Volume 5, 1975, 864 pp.Volume 6, 1977, 765 pp.Volume 7, 1979, 487 pp.Volume 8, 1980, 602 pp.Volume 9, 1981, 596 pp.Volume 10, 1982, 528 pp.Volume 11, 1984, 669 pp.Volume 12, 1986, 643 pp.Table of ContentsReagent Index; Author Index; Type-of-Compound Index; Synthesis Index; Type-of-Reaction Index; Synthetic Targets Index; Thumb Index; Author Index; Other Indexes.

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