Nucleophilic Substitution Reactions of Cyclic Thiosulfinates Are Accelerated by Hyperconjugative Interactions

25 April 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Strain energy has been shown to promote the nucleophilic substitution reactions of cyclic disulfides, the reactivities of cyclic thiosulfinate nucleophilic substitution is unexplored. We used density functional theory calculations [M06-2X/6-311++G(d,p)] to determine the activation and reaction free energies for the reactions of 3—10-membered cyclic thiosulfinates and cyclic disulfides with methyl thiolate.

Keywords

DFT
strain
ring-opening
hyperconjugation

Supplementary materials

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