Izvorni znanstveni članak

Chiroptical Properties and Conformation of 4,5-Saturated Derivatives of 5-Aryl-1,4-benzodiazepin-2-ones

M. Kajtar ; Institute of Organic Chemistry, L. Eotvos University, P. O. Box 325, H-1445 Budapest, Hungary
J. Kajtar ; Institute of Organic Chemistry, L. Eotvos University, P. O. Box 325, H-1445 Budapest, Hungary
J. Rohricht ; Chemical Works of Gedeon Richter, P. O. Box 27, H-1475 Budapest, Hungary
J. G. Angyan ; Chinoin Research Centre, P. o. Box 110, H-1325 Budapest, Hungary

Sažetak

CD spectra of a series of 5-aryl-7-chloro-l,3,4,5-tetrahydro-
2H-l,4-benzodiazepin-2-one derivatives having different substituents
at positions 1, 3, 4, and 5 were studied. The absolute configuration
at C-5 of two homochiral analogues, 1 and 2, having
enantiomorphous ring conformations was determined on the basis
of chiroptical correlations and theoretical calculations. The latter
have shown that the optical activity mainly originates from the
one-electron mechanism and is determined by the helicity of the
diazepine ring, i. e. by the inherent chirality of the partial chromophore 4-chloro-N,2-dimethyl-formanilide. Exciton inter action s
between transitions of the two arornatic chromophores A and C
also give a significant contribution to chiroptical properties. By applying simple chiroptical rules dedueed from experimental
spectra and supported by calculations, the stereochemistry (absolute
conformation and configuration), of 3,5-disubstituted cis and
trans epimeric pairs (7-17) was revealed.

Ključne riječi

Hrčak ID:

175396

URI

https://hrcak.srce.hr/175396

Datum izdavanja:

30.6.1989.

Posjeta: 800 *