Journal of physical organic chemistry vol:16 issue:9 pages:615-625
date:Free Univ Brussels, Eenheid Algemene Chem, B-1050 Brussels, Belgium; Univ Louvain, Dept Chem, B-3001 Louvain, Belgium; HoChiMinh City Univ Technol, Fac Chem Engn, Grp Computat Chem, Thanh Pho Ho Chi Minh, Vietnam
The 1,3-dipolar cycloadditions of diazoalkanes (R2CNN), hydrazoic acid (HNNN) and nitrous oxide (N2O) to some simple dipolarophiles such as acetylenes, phosphaalkynes and cyanides were studied using quantum chemical calculations at the B3LYP/6-311 ++G(d,p) level and, in the simplest case, using also the CCSD(T) method. Along with frontier molecular orbital coefficients, the local softness being a DFT-based reactivity criterion is established as a useful tool to predict the regioselectivity in theses cycloaddition reactions. Copyright (C) 2003 John Wiley Sons, Ltd.