CINDECA   05422
CENTRO DE INVESTIGACION Y DESARROLLO EN CIENCIAS APLICADAS "DR. JORGE J. RONCO"
Unidad Ejecutora - UE
artículos
Título:
THEORETICAL MODELLI NG OF CHIRAL MODIFIER/SUBSTRATE INTERACTION FOR ENANTIOSELECTIVE HYDROGENATION OF p- ISOBUTYLACETOPHENONE
Autor/es:
RECUPERO, FRANCISCO; CASELLA, MÓNICA LAURA; RUGGERA, JOSÉ FERNANDO
Revista:
Anales de la Asociación Química Argentina
Editorial:
Asociación Química Argentina
Referencias:
Lugar: Buenos Aires; Año: 2018 vol. 105 p. 24 - 24
ISSN:
2545-8655
Resumen:
DFT level calculations were carried out to study the interaction between chiral modifier and substrate for Orito type enantioselective hydrogenation. Molecular modelling on a DFT level was developed to study the interaction between (R)-(-)-1-aminoindane and (S)-(+)-1-aminoindane as chiral modifiers and p-isobutylacetophenone (intermediary the synthesis of Ibuprofen). Judging from theoretical calculations and implementing a non-covalent interaction analysis, it was shown that the interaction responsible for the formation of a complex between chiral modifier and substrate is a hydrogen bond. Taking into account the free energies of formation for each complex, a theoretical calculation was performed for the enantiomeric excess obtained from either chiral modifier, finding an excess of about 30% of the R enantiomer product when using (R)-(-)-1-aminoindane, while the excess would be of 30% for the S enantiomer product if the modifier is (S)-(+)-1-aminoindane.
rds']