Bachrach, S.M., Hayes, Joseph, Dao, T. and Mynar, J.L. (2002) Density functional theory gas- and solution-phase study of nucleophilic substitution at di- and trisulfides. Theoretical Chemistry Accounts, 107 (5). pp. 266-271. ISSN 1432881X
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Official URL: http://dx.doi.org/10.1007/s00214-002-0323-4
Density functional calculations indicate that nucleophilic substitution in the thiolate-disulfide and thiolate-trisulfide exchange reactions proceeds by an addition-elimination pathway. Solution calculations were performed using B3LYP/6-31 + G* and the polarized continuum method. These solution-phase calculations indicate that for the reactions where the sulfur under attack bears a hydrogen atom, the substitution proceeds via an addition-elimination mechanism; however, when a methyl group is attached to the sulfur under attack, the SN2 mechanism is predicted.
|Uncontrolled Keywords (separate with ;):||Nucleophilic substitution; Disulfide; Trisulfide; DFT;Solvent effects|
|Subjects:||Physical sciences > Chemistry|
|Schools:||Faculty of Science and Technology > School of Forensic and Applied Sciences|
|Deposited By:||Joseph Hayes|
|Deposited On:||07 Aug 2013 09:49|
|Last Modified:||17 May 2016 12:44|
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