Probing Furanose Ring Conformation by Gas-Phase Computational Methods: Energy Profile and Structural Parameters in Methyl β-d-Arabinofuranoside as a Function of Ring Conformation

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Abstract
The potential energy surface of methyl β-d-arabinofuranoside (3) has been studied by ab initio molecular orbital (HF/6-31G*) and density functional theory (B3LYP/6-31G*) calculations via minimization of the 10 possible envelope conformers. The partial potential energy surface identified that the global minimum and lowest energy northern conformer was E2. In the HF calculations, 2E was the most stable southern conformer, while the density functional theory methods identified 4E as the local minimum in this hemisphere. Additional calculations at higher levels of theory showed that the B3LYP-derived energies of many of the envelope conformers of 3 are dependent upon the basis set used. It has also been demonstrated that B3LYP/6-31+G**//B3LYP/6-31G* single point energies are essentially the same as those obtained from full geometry optimizations at the B3LYP/6-31+G** level. The northern and southern minima of the B3LYP/6-31+G** surface are, respectively, the E2 and 2E conformers. The B3LYP/6-31G* geometries were used to study the relationship between ring conformation and various structural parameters including bond angles, dihedral angles, bond lengths, and interatomic distances.

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