TY - JOUR
T1 - N-hetarylethylenes
T2 - XIII. Conformational analysis and 13C NMR spectra of N-alkenyl derivatives of carbazole, phenoxazine, and phenothiazine
AU - Anfinogenov, V. A.
AU - Khlebnikov, Andrey Ivanovich
AU - Filimonov, V. D.
AU - Ogorodnikov, V. D.
PY - 1999/3
Y1 - 1999/3
N2 - Molecular-mechanics and 13C NMR spectroscopic study of the electronic and steric structure of 9-alkenylcarbazoles, 10-alkenylphenoxazines, and 10-alkenylphenothiazines showed that the phenoxazine and phenothiazine derivatives are chatacterized by nonplanar heterocyclic systems with quasiaxial orientation of the alkenyl group. The phenothiazine system exerts stronger shielding of the terminal carbon atom in the N-vinyl group, as compared to phenoxazine and carbazole. The carbon chemical shifts are directly related to the torsion angles with respect to the C-N bond, indicating a competition between the olefinic double bond and aromatic rings for the unshared electron pair on the nitrogen.
AB - Molecular-mechanics and 13C NMR spectroscopic study of the electronic and steric structure of 9-alkenylcarbazoles, 10-alkenylphenoxazines, and 10-alkenylphenothiazines showed that the phenoxazine and phenothiazine derivatives are chatacterized by nonplanar heterocyclic systems with quasiaxial orientation of the alkenyl group. The phenothiazine system exerts stronger shielding of the terminal carbon atom in the N-vinyl group, as compared to phenoxazine and carbazole. The carbon chemical shifts are directly related to the torsion angles with respect to the C-N bond, indicating a competition between the olefinic double bond and aromatic rings for the unshared electron pair on the nitrogen.
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M3 - Article
AN - SCOPUS:0033089581
VL - 35
SP - 481
EP - 488
JO - Russian Journal of Organic Chemistry
JF - Russian Journal of Organic Chemistry
SN - 1070-4280
IS - 3
ER -