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A Qualitative Valence Bond Model for Organic Reactions

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New Theoretical Concepts for Understanding Organic Reactions

Part of the book series: NATO ASI Series ((ASIC,volume 267))

Abstract

This chapter develops a qualitative methodology for constructing states from their valence bond (VB) building blocks. The essence of the method is a mixing-diagram of the type used in qualitative molecular orbital (MO) theory. The method is used initially to describe states for representative species; a covalent bond, species which possess an average of one electron per site (e.g., allyl radical, etc.,) and mixed-valence species (i.e., molecular ions). Then the method is applied to piece up potential energy profiles for two prototypical reactions (the exchange reactions of H and H−). Finally, the conclusions are generalized to treat complex organic reactions, such as spin-transfer reactions (e.g., radical additions) electrophile-nucleophile combinations, cycloadditions and so on. The origins and variations of barriers and the importance of the quantum mechanical resonance energy of the transition state are discussed.

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Author information

Authors and Affiliations

  1. Department of Chemistry, Ben-Gurion University, Beer Sheva, 84105, Israel

    Sason S. Shaik

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  1. Sason S. Shaik
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Editors and Affiliations

  1. Department of Chemistry, Universitat AutĂ²noma de Barcelona, Spain

    J. BeltrĂ¡n

  2. Department of Chemistry, University of Toronto, Canada

    I. G. Csizmadia

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© 1989 Kluwer Academic Publishers

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Shaik, S.S. (1989). A Qualitative Valence Bond Model for Organic Reactions. In: BeltrĂ¡n, J., Csizmadia, I.G. (eds) New Theoretical Concepts for Understanding Organic Reactions. NATO ASI Series, vol 267. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2313-3_7

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  • DOI: https://doi.org/10.1007/978-94-009-2313-3_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-7539-8

  • Online ISBN: 978-94-009-2313-3

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