Effects of Solvation for (R,R) Tartaric-Acid Amides

Abstract

A review of the most recent applications of the semi-empirical solvation method (SM) as well as results of calculations for (R,R) tartaric-acid amides are presented. Solvation models (SMx) have shown to be efficient in predicting solvation effects for various organic molecules. Effects of solvation, as calculated with the use of SM5.4, alter conformational preferences of isolated molecules of (R,R) tartaric-acid amides, so that in water solution the lowest-energy conformer of the primary amide with respect to the main carbon chain is the trans (T) conformer while for the tertiary amide it is the gauche minus (G−) conformer. The lowest-energy structures of isolated molecules for these amides are gauche plus (G+), stabilized by intramolecular hydrogen bonds. The calculated results are in agreement with the experimental data, which indicate that both in crystal structure and in polar solution the T- and G- conformers are observed for the primary and tertiary amides, respectively. In addition, in non-polar chloroform solvent the G+ structure of the tertiary amide can be observed.KeywordsFree EnergySolvation EffectTartaric AcidNicotinamide Adenine DinucleotideSolvation MethodThese keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.