THEORETICAL MODELLI NG OF CHIRAL MODIFIER/SUBSTRATE INTERACTION FOR ENANTIOSELECTIVE HYDROGENATION OF p- ISOBUTYLACETOPHENONE

RECUPERO, FRANCISCO; CASELLA, MÓNICA LAURA; RUGGERA, JOSÉ FERNANDO

Anales de la Asociación Química Argentina

Asociación Química Argentina

Lugar: Buenos Aires; Año: 2018 vol. 105 p. 24 - 32

2545-8655

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.