Density functional theory gas- and solution-phase study of nucleophilic substitution at di- and trisulfides

Autor:	Justin L. Mynar, Joseph Hayes, Trang Dao, Steven M. Bachrach
Rok vydání:	2002
Předmět:	Substitution reaction chemistry.chemical_compound SNi chemistry Computational chemistry Nucleophilic substitution SN2 reaction chemistry.chemical_element Density functional theory Hydrogen atom Physical and Theoretical Chemistry Sulfur Methyl group
Zdroj:	Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta). 107:266-271
ISSN:	1432-2234 1432-881X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::127c211f5a0b9c80f6fe62b58b2e9530 https://doi.org/10.1007/s00214-002-0323-4 Zobrazit plný text záznamu Full text from SpringerLink