Degenerate intermolecular thiolate-disulfide interchange involving cyclic five-membered disulfides is faster by. apprx. 103 than that involving six-or seven-membered …

R Singh, GM Whitesides

Index: Singh, Rajeeva; Whitesides, George M. Journal of the American Chemical Society, 1990 , vol. 112, # 17 p. 6304 - 6309

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Citation Number: 80

Abstract

Abstract: The rate constants for degenerate intermolecular thiolate-disulfide interchange involving 1, a-dithiolane (S (CH,), S) are higher than those involving 1, fdithiane (S (CH2), S) by a factor of-650 in mixtures of DMSO-d, and D20. The extrapolated rate constant for 1, 2- dithiolane in DMSO-d, is fast (k-IO* M-'s-'). The rate constants for cyclic six-and seven- membered disulfides are similar to those for acyclic disulfides. Rate constants for self- ...