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 has been professor emeritus since 2005 and in 2011 was appointed senior professor of chemistry at the University of Heidelberg. He studied chemistry and completed his doctoral thesis under the supervision of F. Effenberger in Stuttgart in 1964. From 1965 – 1968 he carried out postdoctoral work in the USA, one year with P. v. R. Schleyer at Princeton and two years with Roald Hoffmann at Cornell. He qualified for university teaching (Habilitation) in the laboratory of E. Heilbronner in Basel in 1972 and moved one year later as a full professor to the TU Darmstadt. From 1979 – 2005 he was professor at the University of Heidelberg. His main areas of research have been intra– and intermolecular bonding properties which were studied by synthesizing model systems and through investigations of their interactions by physical measurements supported by quantum chemical calculations. This work resulted in the synthesis of novel cyclophanes, cyclic oligoacetylenes, strained hydrocarbons and vicinal polyketones, and has led to various awards and honorary degrees.

Gebhard Haberhauer is Professor for Organic Chemistry at the University of Duisburg–Essen. He studied chemistry at the Universities of Vienna and Heidelberg and received his Ph.D. from the University of Heidelberg under the supervision of R. Gleiter. From 1999 – 2000 he was a postdoctoral fellow in the laboratory of J. Rebek, Jr. at The Scripps Research Institute in La Jolla. After working one year at BASF in Ludwigshafen, he returned to the University of Heidelberg, where he qualified for university teaching (Habilitation) from 2001 to 2005 under the mentorship of R. Gleiter. In 2005, he was appointed Professor for Organic Chemistry at the University of Duisburg–Essen. His current research interests include chirality induction with azole–containing cyclopeptides and the synthesis of molecular switches and motors.
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