INVESTIGATION OF THE ENANTIOMERIZATION BARRIER OF HOMOFURAN BY COMPUTER-SIMULATION OF INTERCONVERSION PROFILES OBTAINED BY COMPLEXATION GAS-CHROMATOGRAPHY

被引:46
作者
SCHURIG, V [1 ]
JUNG, M [1 ]
SCHLEIMER, M [1 ]
KLARNER, FG [1 ]
机构
[1] RUHR UNIV BOCHUM,FAK CHEM,W-4630 BOCHUM 1,GERMANY
来源
CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 05期
关键词
ENANTIOMERIZATION; DYNAMIC COMPLEXATION GAS CHROMATOGRAPHY; HOMOFURAN;
D O I
10.1002/cber.19921250543
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
By computer simulation of experimental interconversion profiles, obtained by complexation gas chromatography, rate constants of enantiomerization have been determined for homofuran between 95 and 130-degrees-C. Since enantiomerization proceeds at similar rates in the mobile and stationary phase, the rate constants obtained by an Arrhenius plot are in excellent agreement with values determined independently by polarimetry between 60 and 90-degrees-C. We thus demonstrate that dynamic chromatography can be an easy means for the rapid determination of enantiomerization (or isomerization) barriers of ca. 70-120 kJ mol-1 requiring only minute amounts of racemic sample.
引用
收藏
页码:1301 / 1303
页数:3
相关论文
共 16 条
[1]  
[Anonymous], ANGEW CHEM
[2]   DYNAMIC PHENOMENA DURING ENANTIOMER RESOLUTION BY COMPLEXATION GAS-CHROMATOGRAPHY - A KINETIC-STUDY OF ENANTIOMERIZATION [J].
BURKLE, W ;
KARFUNKEL, H ;
SCHURIG, V .
JOURNAL OF CHROMATOGRAPHY, 1984, 288 (01) :1-14
[3]  
ELIEL EL, 1962, STEREOCHEMISTRY CARB, P34
[4]   PROTON MAGNETIC-RESONANCE INVESTIGATION OF INVERSION AT TERVALENT NITROGEN .6. PREPARATIVE SEPARATIONS OF ENANTIOMERIC DIAZIRIDINES BY LIQUID-CHROMATOGRAPHY ON TRIACETYLCELLULOSE - RACEMIZATIONS MONITORED BY POLARIMETRY AND BY H-1-NMR [J].
HAKLI, H ;
MINTAS, M ;
MANNSCHRECK, A .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (06) :2028-2038
[5]   DETERMINATION OF ENANTIOMERIZATION BARRIERS BY COMPUTER-SIMULATION OF INTERCONVERSION PROFILES - ENANTIOMERIZATION OF DIAZIRIDINES DURING CHIRAL INCLUSION GAS-CHROMATOGRAPHY [J].
JUNG, M ;
SCHURIG, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :529-534
[6]  
JUNG M, IN PRESS J CHROMATOG
[7]  
Klarner F.-G., 1987, ANGEW CHEM, V99, P1295
[8]   1,5-ELECTROCYCLIZATION IN HOMOFURAN, HOMOPYRROLE, AND HOMOTHIOPHENE [J].
KLARNER, FG ;
SCHROER, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1294-1295
[9]   EXTENDING THE SCOPE OF ENANTIOMER RESOLUTION BY COMPLEXATION GAS-CHROMATOGRAPHY [J].
SCHURIG, V ;
BURKLE, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) :7573-7580
[10]   SEMIPREPARATIVE ENANTIOMER SEPARATION OF 1-CHLORO-2,2-DIMETHYLAZIRIDINE BY COMPLEXATION GAS-CHROMATOGRAPHY - ABSOLUTE-CONFIGURATION AND BARRIER OF INVERSION [J].
SCHURIG, V ;
LEYRER, U .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :865-868