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Issue 10, 1986
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Molecular mechanics and molecular shape. Part 4. Size, shape, and steric parameters

Amatzya Y. Meyer 

Abstract

To deal with steric effects of substituents on reaction rates, two types of descriptor are proposed. Shape is characterised by the ratio (G) of the substituent's surface area to its volume. Bulk is characterised by the volume (Va) of the portion of the substituent that is within 0.3 nm of the reaction centre. For alkyl substituents, rate constants for several series of reactions (including the classical series, acid hydrolysis of the esters RCO2Et) correlate fairly well with Va and G. Taft's steric parameters (Es) correlate less well. Values of Es for hetero-substituents are found to be contaminated by non-steric factors. It is possible to construe whether the contaminant acts to hinder or to enhance reaction.

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Article type: Paper
DOI: 10.1039/P29860001567
Citation: J. Chem. Soc., Perkin Trans. 2, 1986,0, 1567-1572
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    Molecular mechanics and molecular shape. Part 4. Size, shape, and steric parameters

    A. Y. Meyer, J. Chem. Soc., Perkin Trans. 2, 1986, 0, 1567
    DOI: 10.1039/P29860001567

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