Issue 6, 1990

Marked effect of the shape of solvent molecules on molecular recognition in the oxidation of associating thiols

Abstract

Oxidation of a pair of associating thiols (1 and 2), each having a binding site [–C(O)NHC(O)NH–] and a recognition site (R1 or R2), is examined in binary solvent mixtures of a propanol with water and organic co-solvents. The selectivity (r)—a measure of the degree of recognition of (1) by (2)[or of (2) by (1)]—in the oxidation is represented by the logarithmic ratio of the yield of an unsymmetrical disulphide to twice that of a symmetrical one. It is found that (i) higher selectivity is achieved when the non-polar group of a propanol in a mixed solvent resembles a given non-polar group of one of the reacting molecules in three-dimensional shape and (ii) the above ‘solvent shape effect’ on the selectivity is produced more markedly in aqueous propanols than in the corresponding non-aqueous ones. Correlation of the observed selectivity with physico-chemical properties of (aqueous) propanols, reactivity difference between thiols, and so on is discussed together with a possible explanation of the solvent shape effect on the degree of recognition of non-polar groups.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1990, 1029-1033

Marked effect of the shape of solvent molecules on molecular recognition in the oxidation of associating thiols

T. Endo, H. Takei, T. Isago, K. Guro, Y. Nakajima, J. Kato and M. M. Ito, J. Chem. Soc., Perkin Trans. 2, 1990, 1029 DOI: 10.1039/P29900001029

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