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• W2000736517 abstract "We report here the results on conformational free energies of N-acetyl-N′-methylprolineamide (Ac-Pro-NHMe) and its 5-methylated derivatives calculated using the ab initio and density functional methods with the self-consistent reaction field theory at the HF, MP2, and B3LYP levels of theory with the 6-31+G(d) basis set to investigate the influence of the 5-methylation on the structure, cis–trans equilibrium, and rotational barrier. The steric interactions imposed by the 5-methylation have resulted in the changes in the backbone structure and puckering of proline amides. The shorter distance between the acetyl methyl group and the 5-methyl group for the trans conformer than the cis conformer for each methylated proline amide appears to be crucial in destabilizing the trans conformer. The calculated cis populations and trans-to-cis rotational barriers in chloroform and water are consistent with observed results for Ac-5-MePro-NHMe and Ac-5-t-BuPro-NHMe. By analyzing the contributions to rotational barriers, the isomerization has proved to be entirely enthalpy-driven in the gas phase, chloroform, and water, to which the electronic energies have considerably contributed. The lower rotational barrier for the syn-5-MePro amide than the anti-5-MePro amide is ascribed to the large difference in the electronic energies of TS structures. The sp3 hybridization of the prolyl nitrogen for the TS structures confirmed by analyzing geometrical parameters as well as the pertinent distance between the prolyl nitrogen and the N–H amide group to form a hydrogen bond might indicate that this intramolecular hydrogen bond could contribute in stabilizing the TS structures of proline amide and its 5-methylated amides and play a role in prolyl isomerization." @default.
• W2000736517 created "2016-06-24" @default.
• W2000736517 creator A5083737664 @default.
• W2000736517 date "2002-05-01" @default.
• W2000736517 modified "2023-09-24" @default.
• W2000736517 title "cis – trans Isomerization of N -acetyl- N ′-methylamides of 5-methylproline and 5,5-dimethylproline" @default.
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• W2000736517 doi "https://doi.org/10.1016/s0166-1280(02)00054-4" @default.
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