Concepts and Applications
Buch, Englisch, 320 Seiten, Format (B × H): 157 mm x 235 mm, Gewicht: 612 g
ISBN: 978-1-119-08589-8
Verlag: Wiley
Aromaticity 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 properties. It also provides: - A thorough historical overview of aromaticity, as well as simple electronic and structural models
- Comprehensive explorations of organic and inorganic aromatic compounds, concepts of stability and reactivity, and geometric, energetic, magnetic, and electronic criteria of descriptors of aromaticity
- Practical discussions of heteroaromaticity, as well as Möbius aromaticity and excited state aromaticity
- In-depth examinations of sigma, pi, delta, and phi aromaticity
Perfect for graduate students, researchers, and academics interested in aromaticity, organometallic chemistry, and computational chemistry, Aromaticity and Antiaromaticity: Concepts and Applications will also earn a place in the libraries of professionals and researchers working in organic, inorganic, and physical chemistry.
Autoren/Hrsg.
Fachgebiete
Weitere Infos & Material
Foreword xi
Preface xiii
List of Abbreviations xvii
1 Historical Overview 1
References 7
2 Simple Electron Counting Rules 11
2.1 Introduction 11
2.2 Hückel’s 4n +2 Rule 12
2.3 Baird’s 4n p-Electron Rule for the Lowest-Lying Triplet Excited State 13
2.4 Soncini and Fowler’s Rule 16
2.5 Möbius’ 4n p-Electron Rule 16
2.6 The Linking Number Rule 18
2.7 Platt’s Ring Perimeter Model 19
2.8 Clar’s p-Sextet Rule 20
2.8.1 Glidewell and Lloyd’s Rule 23
2.8.2 The Y-Rule 23
2.9 Hirsch’s 2(n +1)2 Rule 24
2.10 The 2n2 +2n+ 1 (S = n+ 1/2) Rule 26
2.11 Wade–Mingos’ 2n+ 2 Rule 26
2.11.1 Jemmis’ mno Rule 27
2.11.2 Equivalence between Hückel’s andWade–Mingos’ Rules 28
2.12 Other Rules 29
References 30
3 Aromaticity from Organic to Inorganic Compounds 35
3.1 Introduction 35
3.2 p-Aromatic Inorganic Species 36
3.3 Aromaticity in Main Group Metal Compounds 42
3.4 Aromaticity in Transition Metal Compounds 44
3.5 Conclusions 49
References 49
4 Stability and Reactivity in Aromatic Compounds 55
4.1 Introduction 55
4.2 Aromaticity and Thermodynamic Stability 56
4.3 Aromaticity and Kinetic Stability 61
4.3.1 Acenes 61
4.3.2 Pericyclic Reactions 64
4.3.2.1 Diels–Alder Cycloadditions 65
4.3.2.2 [2+2+2] Cycloadditions 67
4.3.2.3 [1,7]-Sigmatropic Migrations 68
4.3.2.4 Fullerene Additions 68
References 72
5 Descriptors of Aromaticity: Geometric Criteria 77
5.1 Introduction 77
5.2 Geometry-Based Estimation of the Molecular Energy 78
5.3 Bond Length Alternation as a Basis for Defining Aromaticity Indices 80
5.3.1 The Julg Aromaticity Index AJ 81
5.3.2 The Harmonic Oscillator Model of Aromaticity,
