Minimalistic amino amides as models to study N–H⋯π interactions and their implication in the side chain folding of pseudopeptidic molecules†,10.1039/C3RA41843J

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Minimalistic amino amides as models to study N–H⋯π interactions and their implication in the side chain folding of pseudopeptidic molecules†

Enrico Faggi,Santiago V. Luis,Ignacio Alfonso

RSC Advances Pub Date : 05/01/2013 00:00:00 , DOI:10.1039/C3RA41843J

Abstract

The structural study of simple amino amides derived from natural amino acids showed a unique conformational pattern for the aromatic residues, being clearly different from that for the aliphatic derivatives. The results from a detailed NMR analysis, supported by DFT calculations, indicate that the aromatic side chain tends to fold over the amino amide moiety, involving a stabilizing polar N–H⋯π interaction. The implications of this folding in the establishing of non-covalent interactions is also discussed.