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Issue 10, 1987
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Volumes of reaction for the formation of some analogues of tetrahedral intermediates

Abstract

Two reactions which comprise equilibrium addition of a protic species to a carbonyl group, the hydroxyketone–hemiacetal interconversion (1a)⇌(1b), and the thiol addition of acetyl cyanide (2a)⇌(2b), have been studied by n.m.r. and their spectra thoroughly analysed. Equilibrium constants have been measured as a function of pressure to obtain volumes of reaction which relate to the formation of the ‘tetrahedral intermediate’ of ester hydrolysis. The intramolecular reaction is shown to have a much less negative volume change than the intermolecular analogue, pointing to the important contribution to ΔV and to ΔV of molecular association prior to bond formation.

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Article type: Paper
DOI: 10.1039/P29870001477
Citation: J. Chem. Soc., Perkin Trans. 2, 1987,0, 1477-1482
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    Volumes of reaction for the formation of some analogues of tetrahedral intermediates

    N. S. Isaacs, H. S. Rzepa, R. N. Sheppard, A. M. Lobo, S. Prabhakar and A. E. Merbach, J. Chem. Soc., Perkin Trans. 2, 1987, 0, 1477
    DOI: 10.1039/P29870001477

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