CONFORMATIONAL-ANALYSIS OF 2-CYANO DIHYDROXYETHANE IN SOLUTION

The conformational space of the 2-cyano-1,1-dihydroxyethane molecule w as studied at the semi-empirical PM3 level and ab initio MP2/6-31G*// 6-31G level in the gas phase and in a low-polarity medium, This system has been chosen as a model compound for 2-cyanocyclohexanone propylen e and ethylene acetals. This has allowed the study of the role of pola r groups on the relative conformation of two adjacent OH groups, which is of interest also in relation to the anomeric effect in carbohydrat e chemistry. Solvent effects are taken into account using a continuum model with general cavity shapes.