| Full text | |
| Author(s): |
Total Authors: 4
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| Affiliation: | [1] Univ Estadual Campinas, Inst Chem, Phys Organ Chem Lab, BR-13083970 Campinas, SP - Brazil
[2] Univ Sao Paulo, Inst Chem, BR-05513970 Sao Paulo - Brazil
Total Affiliations: 2
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| Document type: | Journal article |
| Source: | Journal of Physical Chemistry A; v. 118, n. 9, p. 1748-1758, MAR 6 2014. |
| Web of Science Citations: | 15 |
| 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. (AU) | |
| FAPESP's process: | 12/18567-4 - Conformational investigation of amino acid derivatives and corresponding intramolecular interactions through NMR and IR spectroscopies and theoretical calculations |
| Grantee: | Carolyne Brustolin Braga |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 12/03933-5 - Conformational equilibria and intramolecular interactions for a series of amino-acids: theoretical and experimental approaches |
| Grantee: | Roberto Rittner Neto |
| Support Opportunities: | Regular Research Grants |