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The lone‐pair orbitals of triaziridine
Author(s) -
Kaupp Gerd,
Döhle Jens A.,
Burger Klaus,
Rademacher Paul,
Poppek Rainer
Publication year - 1988
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.610010504
Subject(s) - chemistry , mndo , lone pair , atomic orbital , nitrogen atom , computational chemistry , trifluoromethyl , ionization energy , valence (chemistry) , ionization , molecular orbital , electron pair , bicyclic molecule , fluorine , crystallography , group (periodic table) , stereochemistry , electron , organic chemistry , molecule , ion , physics , alkyl , quantum mechanics
The PE spectra of four stable bicyclic triaziridines with trifluoromethyl, methyl, phenyl, spirocyclopentane and spirocyclohexane substituents are measured. From a comparison of these experimental data with MNDO calculations the energies and the interactions of the nitrogen lone‐pair orbitals were obtained. The trifluoromethyl group may be reliably simulated by a fluorine atom. The ionization potentials are unexpectedly high and so are the cyclovoltammetric anodic potentials. The MNDO valence electron densities are in agreement with the comparatively small differences in the chemical shifts of the differently substituted nitrogens of the triaziridine rings.