Premium
Solvent effect on the stability of mannobiose conformers
Author(s) -
Tvaroska I.,
Perez S.,
Noble O.,
Taravel F.
Publication year - 1987
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360260905
Subject(s) - conformational isomerism , chemistry , solvation , computational chemistry , solvent effects , dipole , dispersion (optics) , crystallography , solvent , molecule , organic chemistry , physics , optics
The conformational equilibria of seven methyl β‐ D ‐mannobioside conformers have been studied theoretically in five solvents. The structure of each individual conformer has been refined by the PCILO quantum‐chemical method from the seven distinct low‐energy regions determined from (Φ, Ψ) maps calculated by a potential function method. The stability of the conformers in dilute solution has been evaluated by using a method that consists of electrostatic, dispersion, and cavity terms. The calculated abundance of conformers depends on the solvent and results indicate that the preponderant conformer in the solution may not be the one adopted by mannobiose in the crystalline form. Based on the determined abundance of conformers, thermodynamically averaged nmr parameters, dipole moment, and linkage rotation have been calculated. The solvation behavior of methyl β‐ D ‐mannobioside is compared to those previously estimated for cellobiose and maltose.