Gas- and solution-phase energetics of the methyl α- and β-D-aldopentofuranosides

The conformational preferences of the furanose rings in methyl U.-D-arabinofuranoside (1), methyl beta-D-arabinofuranoside (2), methyl alpha-D-lyxofuranoside (3), methyl beta-D-lyxofuranoside (4), methyl alpha-D-ribofuranoside (5), methyl beta-D-ribofuranoside (6), methyl (alpha-D-xylofuranoside (7), and methyl l3-Dxylofuranoside (8) have been studied in the gas (B3LYP/6-31+G**//B3LYP/6-31G*) and aqueous (B3LYP/ 6-31+G**//SM5.42/BPW91/6-31G*) phases. The results of these theoretical investigations are compared to previous theoretical and experimental results to determine the northern and southern minima in solution for each glycoside.