info:eu-repo/semantics/article
Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
Registro en:
Cerda García Rojas, Carlos M.; Catalan, Cesar Atilio Nazareno; Muro, Ana Carolina; Joseph Nathan, Pedro; Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia; American Chemical Society; Journal of Natural Products; 71; 6; 6-2008; 967-971
0163-3864
CONICET Digital
CONICET
Autor
Cerda García Rojas, Carlos M.
Catalan, Cesar Atilio Nazareno
Muro, Ana Carolina
Joseph Nathan, Pedro
Resumen
The agreement between theoretical and experimental vibrational circular dichroism curves of (4R,9R,10R)-(+)-african-l(5)-ene-2,6-dione (1) and (4R,9S,10R)-lippifoli-l(6)-en-5-one (2), isolated from the widely used plant Lippia integrifolia, allowed the determination of the conformation and absolute configuration of 1 and confirmed both structural features for 2. Molecular modeling of 1 and 2 was carried out by means of a systematic and a Monte Carlo search protocol followed by geometry optimization employing density functional theory calculations with the B3LYP/6-31G(d), B3LYP/ DGDZVP, and/or B3PW91/DGDZVP2 functionals/basis sets. Validation of the minimum energy conformations for both tricyclic substances was achieved by comparison of the experimental and theoretical vicinal 1H-1H NMR coupling constants obtained by DFT-GIAO calculations. Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Muro, Ana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Joseph Nathan, Pedro. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México