HYDROGEN-BONDING AND IR-SPECTRA OF N-SUBSTITUTED GRANATANINE-3-SPIRO-5'-HYDANTOINS AND NORTROPANE-3-SPIRO-5'-HYDANTOINS

被引:18
作者
BELLANATO, J [1 ]
AVENDANO, C [1 ]
BALLESTEROS, P [1 ]
MARTINEZ, M [1 ]
机构
[1] UNIV COMPLUTENSE MADRID,FAC FARM,DEPT QUIM ORGAN & FARMACEUT,MADRID,SPAIN
关键词
D O I
10.1016/0584-8539(79)80038-0
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
The i.r. spectra of two series of hydantoin spiro derivatives of nortropane and granatanine in the solid state have been studied in the NH and CO stretching regions. Absorption bands due to strong hydrogen bonds between the N3H group and the piperidine nitrogen atom have been observed in the 3000-1800 cm-1 region for almost all compounds. These hydrogen bonds have been confirmed by X-ray data and can be related to the piperidine nitrogen basicity and also to steric effects of the substituent on this nitrogen atom. The i.r. results in the carbonyl region have been compared with Raman data and are interpreted in terms of coupling effects. © 1979.
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页码:807 / 812
页数:6
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