Publicación: Addition reaction of azoles to acetone-d 6: NMR and computational studies
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2024-05-22
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info:eu-repo/semantics/openAccess
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Wiley
Resumen
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 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 Ke vs. 1/T can be used to determine ΔH and ΔS. 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.
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Categorías UNESCO
Palabras clave
Imidazole, pyrazole, triazoles, tetrazole, annular tautomerism, DNMR, acetone addition, DFT calculations
Citación
Rosa M. Claramunt, Dionisia Sanz, Ibon Alkorta, José Elguero, (2024) Addition reaction of azoles to acetone‐d6: NMR and computational studies, Journal of Physical Organic Chemistry. Volume 37, Issue 8, 2024, e4612, ISSN 0894-3230, https://doi.org/10.1002/poc.4612
Centro
Facultades y escuelas::Facultad de Ciencias
Departamento
Química Orgánica y Bio-Orgánica