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Intermolecular interactions that determine the regioselectivity in 1,3‐dipolar cycloadditions of N ‐methyl‐1,3‐oxazolium‐5‐olates with N ‐(phenylmethylene)benzenesulphonamide
Author(s) -
Bonati L.,
Ferraccioli R.,
Moro G.
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080703
Subject(s) - regioselectivity , chemistry , intermolecular force , steric effects , computational chemistry , molecular orbital , reagent , dipole , intermolecular interaction , imidazole , stereochemistry , molecule , organic chemistry , catalysis
1,3‐Dipolar cycloadditions of N ‐(phenylmethylene)benzenesulphonamide with mesionic N ‐methyl‐1,3‐oxazolium‐5‐olates give 2,5‐disubstituted imidazole derivatives with high regioselectivity. The intermolecular interactions underlying this regioselectivity were investigated. The conformational and electronic properties of the reagents were characterized separately. The approach in the early stages of the reactions was then modelled by considering the steric and electrostatic molecular interactions. The interaction energies related to different reaction paths were calculated by perturbation molecular orbital (PMO) treatment and compared.