LOW-TEMPERATURE 2-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION SPECTROSCOPY OF A 1,4-BENZODIAZEPINE

被引:7
作者
LAPLANCHE, LA [1 ]
ROTHCHILD, R [1 ]
机构
[1] CUNY JOHN JAY COLL CRIMINAL JUSTICE,CTR TOXICOL RES & TRAINING,DEPT SCI,NEW YORK,NY 10019
关键词
KETAZOLAM; C-13 NMR CHEMICAL SHIFTS; VARIABLE TEMPERATURE STUDIES; 2D LONG-RANGE C-13-H-1 SHIFT CORRELATION; HINDERED ROTATION; 1,4-BENZODIAZEPINES; LANTHANIDE-INDUCED SHIFTS; BENZODIAZEPINE DRUGS; NMR; C-13;
D O I
10.1080/00387019108018127
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
The unsubstituted phenyl ring in ketazolam, a 1,4-benzodiazepine derivative, has a two-fold rotational barrier about the aryl to tert-alkyl bond connecting this phenyl group to the rest of the molecule. At 50.3 MHz, all twenty of the C-13 resonances of ketazolam are resolved below -40-degrees-C, including two distinct resonances for the ortho carbons and two for the meta carbons. Twelve of the twenty C-13 nuclei resonate between 138 and 125 ppm, necessitating assignment via a combination of one-bond and long-range heteronuclear shift correlation experiments.
引用
收藏
页码:99 / 126
页数:28
相关论文
共 17 条
[2]   AN IMPROVED METHOD FOR HETERONUCLEAR CHEMICAL-SHIFT CORRELATION BY TWO-DIMENSIONAL NMR [J].
BAX, A ;
MORRIS, GA .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (03) :501-505
[3]   NMR OF SOME BENZODIAZEPINE DRUGS - STRUCTURE ELUCIDATION WITH LANTHANIDE-INDUCED SHIFTS OF N-1 SUBSTITUTED BENZODIAZEPINONES [J].
CAZAUX, L ;
VIDAL, C ;
PASDELOUP, M .
ORGANIC MAGNETIC RESONANCE, 1983, 21 (03) :190-195
[4]   C-13 AND PROTON NMR-STUDIES OF 1,4-BENZODIAZEPINES [J].
HARAN, R ;
TUCHAGUES, JP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (07) :1483-1488
[5]   ASSIGNMENT OF CARBONYL CARBONS AND SEQUENCE-ANALYSIS IN PEPTIDES BY HETERONUCLEAR SHIFT CORRELATION VIA SMALL COUPLING-CONSTANTS WITH BROAD-BAND DECOUPLING IN T1 (COLOC) [J].
KESSLER, H ;
GRIESINGER, C ;
ZARBOCK, J ;
LOOSLI, HR .
JOURNAL OF MAGNETIC RESONANCE, 1984, 57 (02) :331-336
[6]   IMPROVED METHOD FOR OPTICAL PURITY DETERMINATION OF KETAZOLAM WITH CHIRAL SHIFT-REAGENT [J].
LAPLANCHE, LA ;
ROTHCHILD, R .
SPECTROSCOPY LETTERS, 1990, 23 (01) :45-64
[7]   THE SOLUTION STRUCTURE OF LIDOCAINE - CONFORMATIONAL-ANALYSIS AND NMR LANTHANIDE-INDUCED SHIFTS [J].
LAPLANCHE, LA ;
VANDERKOOI, G ;
JASMANI, H ;
SUKI, MM .
MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (11) :945-951
[8]  
LAPLANCHE LA, 1990, IN PRESS SPECTROSC L, V23
[9]   LONG-RANGE TWO-DIMENSIONAL HETERONUCLEAR CHEMICAL-SHIFT CORRELATION [J].
MARTIN, GE ;
ZEKTZER, AS .
MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (08) :631-652
[10]   INTERMOLECULAR POTENTIALS FROM CRYSTAL DATA .3. DETERMINATION OF EMPIRICAL POTENTIALS AND APPLICATION TO PACKING CONFIGURATIONS AND LATTICE ENERGIES IN CRYSTALS OF HYDROCARBONS, CARBOXYLIC-ACIDS, AMINES, AND AMIDES [J].
MOMANY, FA ;
CARRUTHERS, LM ;
MCGUIRE, RF ;
SCHERAGA, HA .
JOURNAL OF PHYSICAL CHEMISTRY, 1974, 78 (16) :1595-1620