Conformational analysis of perezone and dihydroperezone using vibrational circular dichroism

Eleuterio Burgueño-Tapia, Carlos M. Cerda-García-Rojas, Pedro Joseph-Nathan

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

24 Citas (Scopus)

Resumen

The vibrational circular dichroism (VCD) spectra of perezone and dihydroperezone measured from CDCl 3 solutions were quite similar, suggesting analogous conformations for both molecules. Their absolute configurations were confirmed by comparison of the experimental VCD spectrum of each compound with curves generated from theoretical calculations using density functional theory (DFT) at the B3LYP/DGDZVP level of theory taking into account their conformational mobility. Conformational analysis of the 8-(R) enantiomer showed 19 low energy conformers in a 2.4 kcal/mol energy range, while for 8-(R), with the saturated side alkyl chain, 34 conformers were considered in the first 2 kcal/mol. Initial analyses were carried out using a Monte Carlo searching with the MMFF94 molecular mechanics force field, all MMFF94 conformers were geometrically optimized using DFT at the B3LYP/6-31G(d) level of theory, followed by reoptimization and calculations of their vibrational frequencies at the B3LYP/DGDZVP level. Good agreement between the theoretical 8-(R) enantiomers and experimental VCD curves were observed for both.

Idioma originalInglés
Páginas (desde-hasta)190-195
Número de páginas6
PublicaciónPhytochemistry
Volumen74
DOI
EstadoPublicada - feb. 2012

Huella

Profundice en los temas de investigación de 'Conformational analysis of perezone and dihydroperezone using vibrational circular dichroism'. En conjunto forman una huella única.

Citar esto