Solvent effects on ozonolysis reaction intermediates (original) (raw)

Solvent effects on relative stability, electronic and molecular structure of ozonolysis reaction intermediates are analyzed with the help of ab initio MP2r6-31q G ) ) calculations. A continuum model is employed to account for solute-solvent electrostatic interactions. The results show that there are large effects on the structure and relative stability of carbonyl oxide by substantially favoring its zwitterionic character. A complex formed by carbonyl oxide and formaldehyde is shown to be stable in the gas phase and in solution. This complex can be involved in solvent cage reactions leading to secondary ozonides. Thermodynamically, primary ozonide decomposition is favored by the solvent. q 1997 Elsevier Science B.V.