{"product_id":"aromaticity-and-antiaromaticity-9781119085898","title":"Aromaticity and Antiaromaticity","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003eAromaticity and Antiaromaticity A comprehensive review of the science of aromaticity, as well as its evolution, from benzene to atomic clusters In Aromaticity and Antiaromaticity: Concepts and Applications, a team of accomplished chemists delivers a comprehensive exploration of the evolution and critical aspects of aromaticity. The book examines the new global criteria used to evaluate aromaticity, including the Nucleus Independent Chemical Shift (NICS) index and the electronic indices based on electronic properties. Additional discussions of inorganic aromatic compounds developed in this century, which give rise to new concepts like multifold aromaticity, are included. Three-dimensional aromaticity found in fullerenes and nanotubes, Möbius aromaticity present in some annulenes, and excited state aromaticity are explored as well. This volume explores the geometrical, electronic, magnetic, and thermodynamic characteristics of aromatic and antiaromatic compounds and their reactivity prop\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003eForeword xi\u003c\/p\u003e \u003cp\u003ePreface xiii\u003c\/p\u003e \u003cp\u003eList of Abbreviations xvii\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Historical Overview \u003c\/b\u003e\u003cb\u003e1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eReferences 7\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Simple Electron Counting Rules \u003c\/b\u003e\u003cb\u003e11\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction 11\u003c\/p\u003e \u003cp\u003e2.2 Hückel’s 4\u003ci\u003en \u003c\/i\u003e+2 Rule 12\u003c\/p\u003e \u003cp\u003e2.3 Baird’s 4\u003ci\u003en \u003c\/i\u003eπ-Electron Rule for the Lowest-Lying Triplet Excited State 13\u003c\/p\u003e \u003cp\u003e2.4 Soncini and Fowler’s Rule 16\u003c\/p\u003e \u003cp\u003e2.5 Möbius’ 4\u003ci\u003en \u003c\/i\u003eπ-Electron Rule 16\u003c\/p\u003e \u003cp\u003e2.6 The Linking Number Rule 18\u003c\/p\u003e \u003cp\u003e2.7 Platt’s Ring Perimeter Model 19\u003c\/p\u003e \u003cp\u003e2.8 Clar’s π-Sextet Rule 20\u003c\/p\u003e \u003cp\u003e2.8.1 Glidewell and Lloyd’s Rule 23\u003c\/p\u003e \u003cp\u003e2.8.2 The Y-Rule 23\u003c\/p\u003e \u003cp\u003e2.9 Hirsch’s 2(\u003ci\u003en \u003c\/i\u003e+1)2 Rule 24\u003c\/p\u003e \u003cp\u003e2.10 The 2\u003ci\u003en\u003c\/i\u003e2 +2\u003ci\u003en\u003c\/i\u003e+ 1 (S = \u003ci\u003en\u003c\/i\u003e+ 1\/2) Rule 26\u003c\/p\u003e \u003cp\u003e2.11 Wade–Mingos’ 2\u003ci\u003en\u003c\/i\u003e+ 2 Rule 26\u003c\/p\u003e \u003cp\u003e2.11.1 Jemmis’ \u003ci\u003emno \u003c\/i\u003eRule 27\u003c\/p\u003e \u003cp\u003e2.11.2 Equivalence between Hückel’s andWade–Mingos’ Rules 28\u003c\/p\u003e \u003cp\u003e2.12 Other Rules 29\u003c\/p\u003e \u003cp\u003eReferences 30\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Aromaticity from Organic to Inorganic Compounds \u003c\/b\u003e\u003cb\u003e35\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction 35\u003c\/p\u003e \u003cp\u003e3.2 π-Aromatic Inorganic Species 36\u003c\/p\u003e \u003cp\u003e3.3 Aromaticity in Main Group Metal Compounds 42\u003c\/p\u003e \u003cp\u003e3.4 Aromaticity in Transition Metal Compounds 44\u003c\/p\u003e \u003cp\u003e3.5 Conclusions 49\u003c\/p\u003e \u003cp\u003eReferences 49\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Stability and Reactivity in Aromatic Compounds \u003c\/b\u003e\u003cb\u003e55\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction 55\u003c\/p\u003e \u003cp\u003e4.2 Aromaticity and Thermodynamic Stability 56\u003c\/p\u003e \u003cp\u003e4.3 Aromaticity and Kinetic Stability 61\u003c\/p\u003e \u003cp\u003e4.3.1 Acenes 61\u003c\/p\u003e \u003cp\u003e4.3.2 Pericyclic Reactions 64\u003c\/p\u003e \u003cp\u003e4.3.2.1 Diels–Alder Cycloadditions 65\u003c\/p\u003e \u003cp\u003e4.3.2.2 [2+2+2] Cycloadditions 67\u003c\/p\u003e \u003cp\u003e4.3.2.3 [1,7]-Sigmatropic Migrations 68\u003c\/p\u003e \u003cp\u003e4.3.2.4 Fullerene Additions 68\u003c\/p\u003e \u003cp\u003eReferences 72\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Descriptors of Aromaticity: Geometric Criteria \u003c\/b\u003e\u003cb\u003e77\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction 77\u003c\/p\u003e \u003cp\u003e5.2 Geometry-Based Estimation of the Molecular Energy 78\u003c\/p\u003e \u003cp\u003e5.3 Bond Length Alternation as a Basis for Defining Aromaticity Indices 80\u003c\/p\u003e \u003cp\u003e5.3.1 The Julg Aromaticity Index AJ 81\u003c\/p\u003e \u003cp\u003e5.3.2 The Harmonic Oscillator Model of Aromaticity, HOMA (1972 and 1993) 82\u003c\/p\u003e \u003cp\u003e5.4 Separation of HOMA into Two Components EN and GEO (1996) 85\u003c\/p\u003e \u003cp\u003e5.5 Harmonic Oscillator Model of Electron Delocalization, HOMED (2007) 86\u003c\/p\u003e \u003cp\u003e5.6 Harmonic Oscillator Model for Heterocycles with π Electron and\/or \u003ci\u003en\u003c\/i\u003e-Electron Delocalization: The HOMHED Index (2012) 87\u003c\/p\u003e \u003cp\u003e5.7 Applications of the Bond Orders for Estimating Aromaticity 88\u003c\/p\u003e \u003cp\u003e5.8 Bird’s Aromaticity Indices \u003ci\u003eI\u003c\/i\u003e5 and \u003ci\u003eI\u003c\/i\u003e6 (1985) 90\u003c\/p\u003e \u003cp\u003e5.9 Pozharskii Criterion of Aromaticity, Δ\u003ci\u003eN \u003c\/i\u003e(1985) and Bond Alternation Coefficient, BAC (1995) 90\u003c\/p\u003e \u003cp\u003e5.10 Applications 91\u003c\/p\u003e \u003cp\u003e5.11 Impact of the Electric Field on Aromaticity 94\u003c\/p\u003e \u003cp\u003e5.12 Stacking Interactions versus H-Bonding in Nucleobases 95\u003c\/p\u003e \u003cp\u003e5.13 Showing the Interaction Path for Substituent Effects 96\u003c\/p\u003e \u003cp\u003e5.14 Applications in the Field of Quasiaromatic Systems 100\u003c\/p\u003e \u003cp\u003e5.15 Extension of HOMA to Noncyclic and Non-π-electron Systems 101\u003c\/p\u003e \u003cp\u003e5.16 Conclusions 103\u003c\/p\u003e \u003cp\u003eReferences 104\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Descriptors of Aromaticity: Energetic Criteria \u003c\/b\u003e\u003cb\u003e111\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction 111\u003c\/p\u003e \u003cp\u003e6.2 Thermochemical Approaches 114\u003c\/p\u003e \u003cp\u003e6.3 Energetic Approaches Based on Molecular Geometry 115\u003c\/p\u003e \u003cp\u003e6.4 Theoretical Approaches 117\u003c\/p\u003e \u003cp\u003eReferences 126\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Descriptors of Aromaticity: Magnetic Criteria \u003c\/b\u003e\u003cb\u003e131\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction 131\u003c\/p\u003e \u003cp\u003e7.2 NMR Chemical Shifts 134\u003c\/p\u003e \u003cp\u003e7.3 Nucleus Independent Chemical Shifts 135\u003c\/p\u003e \u003cp\u003e7.4 Magnetically Induced Current Densities 138\u003c\/p\u003e \u003cp\u003e7.5 Anisotropy of the Induced Current Density Tensor 140\u003c\/p\u003e \u003cp\u003eReferences 141\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Descriptors of Aromaticity: Electronic Criteria \u003c\/b\u003e\u003cb\u003e145\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction 145\u003c\/p\u003e \u003cp\u003e8.2 Density Functions 146\u003c\/p\u003e \u003cp\u003e8.3 Measures of Electron Delocalization 150\u003c\/p\u003e \u003cp\u003e8.3.1 The Electron Sharing Indices (ESI) 150\u003c\/p\u003e \u003cp\u003e8.3.2 The Electron Localization Function (ELF) 152\u003c\/p\u003e \u003cp\u003e8.4 Electronic Descriptors of Aromaticity 155\u003c\/p\u003e \u003cp\u003eReferences 160\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Heteroaromaticity \u003c\/b\u003e\u003cb\u003e165\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction 165\u003c\/p\u003e \u003cp\u003e9.2 Six-Membered Organic and Inorganic Heterocycles 168\u003c\/p\u003e \u003cp\u003e9.3 Polycyclic Heteroaromatic Hydrocarbons 178\u003c\/p\u003e \u003cp\u003e9.4 Five-Membered Organic Heterocycles 179\u003c\/p\u003e \u003cp\u003e9.5 Aromaticity of Nucleic Bases 183\u003c\/p\u003e \u003cp\u003eReferences 187\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Möbius Aromaticity \u003c\/b\u003e\u003cb\u003e193\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction 193\u003c\/p\u003e \u003cp\u003e10.2 Metallacyclic Möbius Aromatic Species 197\u003c\/p\u003e \u003cp\u003e10.3 Macrocyclic Möbius Aromaticity 199\u003c\/p\u003e \u003cp\u003eReferences 204\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 \u003c\/b\u003e\u003cb\u003e𝛔-, \u003c\/b\u003e\u003cb\u003e𝛑-, \u003c\/b\u003e\u003cb\u003e𝛅-, and \u003c\/b\u003e\u003cb\u003e𝛗-Aromaticity \u003c\/b\u003e\u003cb\u003e207\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction 207\u003c\/p\u003e \u003cp\u003e11.2 σ-Aromatic and σ-Antiaromatic Species 209\u003c\/p\u003e \u003cp\u003e11.2.1 σ-Aromatic Species 209\u003c\/p\u003e \u003cp\u003e11.2.2 σ-Antiaromatic Species 210\u003c\/p\u003e \u003cp\u003e11.3 σ-, π-Doubly Aromatic, and σ-, π-Doubly Antiaromatic Species and Species with σ-, π-Conflicting Aromaticity 211\u003c\/p\u003e \u003cp\u003e11.3.1 σ-, π-Doubly Aromatic Species 211\u003c\/p\u003e \u003cp\u003e11.3.2 σ-, π-Doubly Antiaromatic Species 212\u003c\/p\u003e \u003cp\u003e11.3.3 Species with σ-Antiaromaticity and π-Aromaticity 213\u003c\/p\u003e \u003cp\u003e11.3.4 Species with σ-Aromaticity and π-Antiaromaticity 214\u003c\/p\u003e \u003cp\u003e11.4 δ-Aromaticity 215\u003c\/p\u003e \u003cp\u003e11.5 ϕ-Aromaticity 218\u003c\/p\u003e \u003cp\u003e11.6 Conclusions 219\u003c\/p\u003e \u003cp\u003eReferences 220\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 The Distortivity of \u003c\/b\u003e\u003cb\u003e𝛑-Electrons \u003c\/b\u003e\u003cb\u003e223\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction 223\u003c\/p\u003e \u003cp\u003e12.2 The Kekulean Distortion 224\u003c\/p\u003e \u003cp\u003e12.3 Frequencies of the Kekulé Vibrational Mode in Benzene 225\u003c\/p\u003e \u003cp\u003e12.4 Changes in Aromaticity in the Kekulean Distortion 227\u003c\/p\u003e \u003cp\u003e12.5 The Maximum Hardness and Minimum Polarizability Principles 228\u003c\/p\u003e \u003cp\u003e12.6 The Distortive Nature of π-Electrons 229\u003c\/p\u003e \u003cp\u003e12.7 Conclusions 236\u003c\/p\u003e \u003cp\u003eReferences 236\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 Three-Dimensional Aromaticity \u003c\/b\u003e\u003cb\u003e241\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e13.1 Introduction 241\u003c\/p\u003e \u003cp\u003e13.2 Spherical Aromaticity 242\u003c\/p\u003e \u003cp\u003e13.2.1 Aromaticity on the Surface of the Sphere 242\u003c\/p\u003e \u003cp\u003e13.2.2 Aromaticity Inside the Sphere 247\u003c\/p\u003e \u003cp\u003e13.2.2.1 \u003ci\u003eCloso \u003c\/i\u003eBoranes 248\u003c\/p\u003e \u003cp\u003e13.2.2.2 Jellium Cluster Model 250\u003c\/p\u003e \u003cp\u003e13.3 Octahedral Aromaticity 251\u003c\/p\u003e \u003cp\u003e13.4 Cubic Aromaticity 253\u003c\/p\u003e \u003cp\u003e13.5 Tetrahedral Aromaticity 255\u003c\/p\u003e \u003cp\u003e13.6 Cylindrical Aromaticity 256\u003c\/p\u003e \u003cp\u003eReferences 259\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Excited State Aromaticity \u003c\/b\u003e\u003cb\u003e265\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction 265\u003c\/p\u003e \u003cp\u003e14.2 Theoretical and Experimental Studies of Excited State Aromaticity 266\u003c\/p\u003e \u003cp\u003e14.2.1 Theoretical and Computational Studies 267\u003c\/p\u003e \u003cp\u003e14.2.2 Experimental Studies 269\u003c\/p\u003e \u003cp\u003e14.3 Influence of Aromaticity in the Excited State Properties 271\u003c\/p\u003e \u003cp\u003e14.3.1 Molecular Dipole Moments 271\u003c\/p\u003e \u003cp\u003e14.3.2 Singlet-Triplet Energy Gaps 272\u003c\/p\u003e \u003cp\u003e14.3.3 Photoacidity 273\u003c\/p\u003e \u003cp\u003e14.4 Influence of Aromaticity in the Excited State Reactivity 274\u003c\/p\u003e \u003cp\u003e14.4.1 Photoisomerizations 275\u003c\/p\u003e \u003cp\u003e14.4.2 Excited State Intramolecular Proton Transfer 276\u003c\/p\u003e \u003cp\u003e14.4.3 Photochemical Formation of \u003ci\u003eOrtho\u003c\/i\u003e-Xylylenes 278\u003c\/p\u003e \u003cp\u003e14.4.4 Photochemical Pericyclic Reactions 279\u003c\/p\u003e \u003cp\u003eReferences 281\u003c\/p\u003e \u003cp\u003eIndex 285\u003c\/p\u003e","brand":"John Wiley \u0026 Sons Inc","offers":[{"title":"Default Title","offer_id":49406981865815,"sku":"9781119085898","price":112.5,"currency_code":"GBP","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0817\/1739\/5799\/files\/9781119085898.jpg?v=1730497779","url":"https:\/\/bookcurl.com\/products\/aromaticity-and-antiaromaticity-9781119085898","provider":"Book Curl","version":"1.0","type":"link"}