Adiabatic φ/ψ maps for cellobiose were prepared with B3LYP density functional theory. A mixed basis set was used for minimization, followed with 6-31+G(d) single-point calculations, with and without SMD continuum solvation. Different arrangements of the exocyclic groups (38 starting geometries) were considered for each φ/ψ point. The vacuum calculations agreed with earlier computational and experimental results on the preferred gas phase conformation (anti-φ H, syn-ψ H), and the results from the solvated calculations were consistent with the (syn φ H/ψ H conformations from condensed phases (crystals or solutions). Results from related studies were compared, and there is substantial dependence on the solvation model as well as arrangements of exocyclic groups. New stabilizing interactions were revealed by Atoms-In-Molecules theory.
Bibliographical noteFunding Information:
Monica Concha, senior technician, carried out many of the calculations including the AIM analyses. Martin Frank and Carlos Stortz kindly commented on a draft of this manuscript. Support for A.D.F., G.P.J. and M.C. came from normal USDA-ARS appropriations. Supplementary funding associated with this effort came from Cotton, Incorporated. This work is connected to the scientific program of the ‘Development of quality-oriented and harmonized R + D + I strategy and functional model at BME’ project, supported by the New Hungary Development Plan (Project ID: TA´ MOP-4.2.1/B-09/1/KMR-2010-0002).
- Aqueous solvation
- Conformational analysis