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 |
Files in This Item:
File | Size | Format | |
---|---|---|---|
000332756100022.pdf | 2.97 MB | Adobe PDF | View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.