Addition reaction of azoles to acetone‐ d 6 : NMR and computational studies

The reactivity of imidazole, pyrazole, 1,2,4‐triazole, 1,2,3‐triazole, and tetrazole with acetone (propan‐2‐one) has been studied by 1 H and 13 C NMR using acetone‐ d 6 as solvent at temperatures ranging from 173 to 300 K at 10 K intervals. Simultaneously, the reaction has been theoretically calcula...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2024-08, Vol.37 (8)
Main Authors: Claramunt, Rosa M., Sanz, Dionisia, Alkorta, Ibon, Elguero, José
Format: Article
Language:English
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Summary:The reactivity of imidazole, pyrazole, 1,2,4‐triazole, 1,2,3‐triazole, and tetrazole with acetone (propan‐2‐one) has been studied by 1 H and 13 C NMR using acetone‐ d 6 as solvent at temperatures ranging from 173 to 300 K at 10 K intervals. Simultaneously, the reaction has been theoretically calculated at the B3LYP/6‐311++G(d,p) level, and experimental and theoretical results have been compared. The equilibrium constants between azoles and adducts α,α‐dimethyl‐azole‐methanol were analyzed, assuming that the straight part of the plots –R ln K e vs. 1/T can be used to determine Δ H and Δ S . Calculated and experimental data are related, but the theoretical values are proportionally higher. The tautomerism of triazoles and tetrazole has been considered in order to discuss the reactions.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.4612