Theoretical studies on the conformation of saccharides. XIV. Structure and conformational properties of the glycosylamines.
The 2-methylaminotetrahydropyran was used as a model to study conformational properties of the N-glycosidic linkage in glycosylamines. Relaxed two-dimensional conformational (phi, psi) maps in 20 solvents were calculated by a method in which the total energy is divided into the energy of the isolated molecule and the solvation energy. Molecular geometry optimization has been carried out for each conformer using the quantum chemical method PCILO. The calculated variations of the geometry are consistent with the results obtained by the statistical analysis of available experimental data retrieved from the Cambridge Structural Database. The calculated abundances of conformers show that the polarity of the solvent has little effect on the anomeric ratio, and the form having the methylamino group equatorial is favored in all considered solvents.
Kozár
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T
Institute of Experimental Physics, Slovak Academy of Sciences, Kosice, Czechoslovakia.
Tvaroska
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I
D002236:Carbohydrate Conformation; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D011714:Pyrans
D011714:Pyrans; C065468:2-methylaminotetrahydropyran