Computational chemical studies of chiral stationary phase models : Complexes of methyl N-(2-naphthyl)alaninate with N-(3,5-dinitrobenzoyl)leucine n-propylamide

✍ Scribed by Sid Topiol; Michael Sabio

• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 559 KB
• Volume: 461
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(00)94282-1

✦ Synopsis

Recent computational chemical studies on @)-methyl N-(2-naphthyl)alaninate with (S)-and (R)-N-(3,5dinitrobenzoyl)leucine n-propylamide were further refined by using semi-empirical quantum-chemical methods for determining structural and energetic parameters. These results confirm the earlier prediction that the same three primary interactions ("contact points") that others have proposed for the SS complex can also be achieved by the less stable SR complex without significant additional energy. Thus, a classical three-point mechanism for chiral recognition is not expected to be operative in this interaction model. We have verified earlier predictions that the computationally determined repulsive nature of the x interaction could become attractive through the use of more refined calculations, while still maintaining the equality between the SS and SR complexes.