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PMO Analysis of Cycloadditions, III 1) . Regioselectivity and Reactivity in Cycloadditions of Formonitrile Oxide
Author(s) -
Sustmann Reiner,
Sicking Willi
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200903
Subject(s) - chemistry , regioselectivity , molecular orbital , stereochemistry , non covalent interactions , computational chemistry , ab initio , crystallography , molecule , organic chemistry , hydrogen bond , catalysis
Cycloadditions of formonitrile oxide are studied by an all‐valence electron perturbation treatment. The activated complex is modeled according to the calculated transition state for the addition of formonitrile oxide to acetylene. The separation of the interaction energy in polar, noncovalent, and covalent contributions shows the type II behavior of formonitrile oxide in the classification scheme of 1,3‐dipolar cycloadditions and demonstrates that the regioselectivity can be explained better by the noncovalent repulsion than by the frontier molecular orbital stabilisations. A discussion of regioselectivity in terms of the magnitude of the eigenvector coefficients in the FMOs does not give satisfactory results.