Aromaticity and Other Conjugation Effects

  • ID: 2180093
  • Book
  • 466 Pages
  • John Wiley and Sons Ltd
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The authors provide an excellent overview of conjugation effects in organic chemistry within and between Pi systems. Besides various

aspects of aromaticity one finds detailed discussions of homo–, spiroand hyperconjugation as well as effects of through–space and throughbond interactions. These effects are presented on the basis of experimental results and are analyzed by the use of qualitative arguments of perturbation theory and from a comparison with results from high level ab initio calculations.

This book is a must–have for bachelor students from the second year on, master and PhD students of chemistry. Also students in science

such as physics, biology and medicine will benefit from the concepts described in the book. Furthermore, chemists in research and development will be grateful to find here an overview of conjugation effects allowing to understand the structures, the dynamics and the reactivity of molecules.

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CONJUGATED pi–SYSTEMS

Linear Conjugated Polyenes

Conjugated Oligoalkynes

Conjugated Planar Monocyclic Systems

Aromaticity Criteria

Structures of Monocyclic (4n)pi and (4n+2)pi Annulenes

Conjugated Polycyclic Planar pi Electron Systems

Substituent Effects

Conjugation in Two and Three Dimensions

THROUGH–SPACE INTERACTION BETWEEN pi SYSTEMS

Homoconjugation

Transannular Effects

Homoaromatic Systems

Spiroconjugation

DONOR–ACCEPTOR INTERACTIONS BETWEEN PLANAR ARENES

Donor–Acceptor Complexes

Structures of Benzene and Related Aromatics in the Solid State

Interactions Between Molecules of Opposite Electric Quadrupole Moments

Model Studies to Measure the Strength of Non–Covalent Interactions Between pi Systems in Organic Solvents

Model Calculations on pi–pi Interactions

Applications and Consequences of pi–pi Interactions of Arenes in Chemistry

THROUGH–BOND INTERACTION BETWEEN pi SYSTEMS AND NON–BONDING ELECTRON PAIRS OF HETEROATOMS

Theoretical Models

Dehydroaromatics

Through–Bond Interaction Between Non–Conjugated pi Systems

Rationalization of Intramolecular Reactivity by Through–Bond Coupling

HYPERCONJUGATIVE INTERACTIONS

Concept of the Two–Electron/Two–Orbital Interactions

Definition and Manifestation on Ground State Properties

Positive Hyperconjugation (sigma–p, sigma–pi∗ and sigma–sigma∗ Interactions)

Negative Hyperconjugation (n–sigma∗ and pi–sigma∗ Interactions)

THEORETICAL METHODS

Quantum Chemical Calculation Methods –

An Overview

Orbital Interactions

Spectroscopic Methods for Detecting Conjugation Effects

APPENDIX

Character Tables for Selected Symmetry Groups

Basic Equations for Nuclear Magnetic Shielding in Molecules

Energy Conversion Table and Abbreviations

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Rolf Gleiter
G. Haberhauer
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