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Issue 8, 1977
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Hydrogen bonding abilities and self-association of some potentially bifunctional catalysts. Part 2. Mercaptoazole derivatives

Emilie Gentric,  Jacques Lauransan,  Christian Roussel  and  Jacques Metzger 

Abstract

Hydrogen bonding abilities of 2-mercaptoazoles (1)–(3) towards dimethyl sulphoxide (KA) or 4-chlorophenol (KB) have been studied quantitatively in CCl4 by i.r. spectroscopy at 25 °C. The N–H proton of mercaptoazoles exhibits a high tendency to hydrogen bonding (40 < KA < 3 000 l mol–1) which is correlated with the basicity of the 2-alkylazole analogues. The C[double bond, length half m-dash]S sulphur atom shows good hydrogen bonding ability (20 < KB < 250 l mol–1) which roughly parallels its nucleophilic reactivity towards methyl iodide. Knowledge of the KA and KB constants allows a better understanding of the factors which affect the self-association constants of mercaptoazoles (100 < KD < 4 700 l mol–1).

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Article type: Paper
DOI: 10.1039/P29770001015
Citation: J. Chem. Soc., Perkin Trans. 2, 1977,0, 1015-1019
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    Hydrogen bonding abilities and self-association of some potentially bifunctional catalysts. Part 2. Mercaptoazole derivatives

    E. Gentric, J. Lauransan, C. Roussel and J. Metzger, J. Chem. Soc., Perkin Trans. 2, 1977, 0, 1015
    DOI: 10.1039/P29770001015

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