Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/56499
Type: Artigo
Title: Conformational analysis and intramolecular interactions of l-proline methyl ester and its N-acetylated derivative through spectroscopic and theoretical studies
Author: Braga, Carolyne B.
Ducati, Lucas C.
Tormena, Claudio F.
Rittner, Roberto
Abstract: This work reports a detailed study regarding the conformational preferences of L-proline methyl ester (ProOMe) and its N-acetylated derivative (AcProOMe) to elucidate the effects that rule their behaviors, through nuclear magnetic resonance (NMR) and infrared (IR) spectroscopies combined with 00113 theoretical calculations. These compounds do not present a zwitterionic form in solution, simulating properly amino acid residues in biological media, in a way closer than amino acids in the gas phase. Experimental (3)J(HH) coupling constants and infrared data showed excellent agreement with theoretical calculations, indicating no variations in conformer populations on changing solvents. Natural bond orbital (NBO) results showed that hyperconjugative interactions are responsible for the higher stability of the most populated conformer of ProOMe, whereas for AcProOMe both hyperconjugative and steric effects rule its conformational equilibrium.
This work reports a detailed study regarding the conformational preferences of l-proline methyl ester (ProOMe) and its N-acetylated derivative (AcProOMe) to elucidate the effects that rule their behaviors, through nuclear magnetic resonance (NMR) and infr
Subject: Análise conformacional
Aminoácidos
Espectroscopia de ressonância magnética nuclear
Espectroscopia de infravermelho
Cálculos teóricos
Country: Estados Unidos
Editor: American Chemical Society
Citation: Journal Of Physical Chemistry A. Amer Chemical Soc, v. 118, n. 9, n. 1748, n. 1758, 2014.
Rights: fechado
Identifier DOI: 10.1021/jp5007632
Address: https://pubs.acs.org/doi/full/10.1021/jp5007632
Date Issue: 2014
Appears in Collections:IQ - Artigos e Outros Documentos

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