Mechanism of 4‐methyl‐1,2,4‐triazol‐3‐thiole reaction with formaldehyde. A DFT study |
| |
| Authors: | Monika Wujec Piotr Paneth |
| |
| Affiliation: | 1. Department of Organic Chemistry, Faculty of Pharmacy, Medical University, Staszica 6, 20‐081 Lublin, Poland;2. Institute of Applied Radiation Chemistry, Technical University of Lodz, Zeromskiego 116, 90‐924 Lodz, PolandInstitute of Applied Radiation Chemistry, Technical University of Lodz, Zeromskiego 116, 90‐924 Lodz, Poland.=== |
| |
| Abstract: | 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 N? C bond rather than the S? C 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 S? C bond formation is about 5 kcal/mol more energetically demanding. Copyright © 2007 John Wiley & Sons, Ltd. |
| |
| Keywords: | 1,2,4‐triazole tautomerization DFT theoretical calculations |
|
|
