Premium
Mechanism of 4‐methyl‐1,2,4‐triazol‐3‐thiole reaction with formaldehyde. A DFT study
Author(s) -
Wujec Monika,
Paneth Piotr
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1250
Subject(s) - chemistry , formaldehyde , solvent , reaction mechanism , nucleophilic substitution , computational chemistry , gibbs free energy , sulfur , transition state , activation energy , molecule , nucleophile , solvent effects , atom (system on chip) , medicinal chemistry , organic chemistry , catalysis , thermodynamics , physics , computer science , embedded system
Contrary to the typical nucleophilic substitution, occurring on the sulfur atom of 4‐methyl‐1,2,4‐ triazol‐3‐thiole, the reaction with formaldehyde leads to the formation of the NC bond rather than the SC bond. The mechanism of this reaction has been characterized theoretically. Calculations indicate that the reaction proceeds via a cyclic transition state involving one solvent molecule with the Gibbs free activation energy of only 2 kcal/mol. The alternative pathway that leads to the SC bond formation is about 5 kcal/mol more energetically demanding. Copyright © 2007 John Wiley & Sons, Ltd.