Four-membered ring cyclic ketene -O,O-, -O,S-, -O,N-, -S,S-, -S,N-, and -N,N-acetals and their corresponding cations: a computational study

摘要

A systematic computational study of four-membered cyclic ketene - O,O -, - O,S -, - O,N -, - S,N - and - N,N -acetals as well as their protonated analogs have been performed at the second order M?ller Plesset level with a polarized triple zeta basis set. The main purpose of this study was to make predictions about the nucleophilicity of these systems and the variations in nucleophilicity with the hetero atoms. Our calculations suggest that all six target molecules are good nucleophiles, and that the N,N analog is the strongest and the S,S analog the weakest nucleophile. Our results include molecular geometries, bond lengths, proton affinities, vibrational frequencies, and calculated charges.