Acidity functions in strongly basic meida. Part III. The ionisation of pentamethylphenol in methanolic sodium methoxide solutions and the inference of steric inhibition of solvation from acidity function data

Journal of the Chemical Society B: Physical Organic Pub Date: DOI: 10.1039/J29660000121

Abstract

The ionisation of pentamethylphenol in concentrated methanolic sodium methoxide solutions parallels an H– acidity function which deviates less from ideality than the corresponding function deduced from the ionisation of t-butyl phenols. The results are consistent with the possibility that steric inhibition of solvation of the phenol anions by bulky ortho substituents is reflected not only in the acid ionisation constants of the phenols but also in the variation of acidity functions with sodium methoxide concentration.

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