CONFORMATIONAL MOBILITY IN CHEMICALLY-MODIFIED CYCLODEXTRINS

被引：24

作者：

ELLWOOD, P ^{[1
]}

SPENCER, CM ^{[1
]}

SPENCER, N ^{[1
]}

STODDART, JF ^{[1
]}

ZARZYCKI, R ^{[1
]}

机构：

[1] UNIV SHEFFIELD,DEPT CHEM,SHEFFIELD S3 7HF,S YORKSHIRE,ENGLAND

来源：

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY | 1992年 / 12卷 / 1-4期

关键词：

CHEMICALLY-MODIFIED CYCLODEXTRINS; CONFORMATIONAL ANALYSIS; NMR SPECTROSCOPY;

D O I：

10.1007/BF01053857

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The observation that per-2,6-O-methyl-3-O-benzoyl-alpha-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-alpha-cyclodextrin (3) and some related compounds (7-9) between conformational isomers with averaged C6 and C3 molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9-degrees in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species with C3 molecular symmetry, to +92-degrees in acetone where a species with averaged C6 symmetry is present.

引用

页码：121 / 150

页数：30

共 47 条

[1] 2ND-SPHERE COORDINATION OF CARBOPLATIN AND RHODIUM COMPLEXES BY CYCLODEXTRINS (CYCLOMALTO-OLIGOSACCHARIDES)
ALSTON, DR
ASHTON, PR
LILLEY, TH
STODDART, JF
ZARZYCKI, R
SLAWIN, AMZ
WILLIAMS, DJ
[J]. CARBOHYDRATE RESEARCH, 1989, 192 : 259 - 281
[2] [Anonymous], 1971, STEREOCHEMISTRY CARB
[3] LONG-RANGE PROTON C-13 NMR SPIN COUPLING-CONSTANTS
BAX, A
FREEMAN, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) : 1099 - 1100
[4] Bender M. L., 1978, CYCLODEXTRIN CHEM, DOI [10.1007/978-3-642-66842-5, DOI 10.1007/978-3-642-66842-5]
[5] BERGERON RJ, 1984, INCLUSION COMPOUNDS, V2, P391
[6] CONFORMATIONAL DEPENDENCE OF C-13 NUCLEAR-MAGNETIC-RESONANCE CHEMICAL-SHIFTS IN OLIGOSACCHARIDES
BOCK, K
BRIGNOLE, A
SIGURSKJOLD, BW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (11): : 1711 - 1713
[7] CYCLODEXTRIN CHEMISTRY - SELECTIVE MODIFICATION OF ALL PRIMARY HYDROXYL-GROUPS OF ALPHA-CYCLODEXTRINS AND BETA-CYCLODEXTRINS
BOGER, J
CORCORAN, RJ
LEHN, JM
[J]. HELVETICA CHIMICA ACTA, 1978, 61 (06) : 2190 - 2218
[8] BRESLOW R, 1984, INCLUSION COMPOUNDS, V3, P473
[9] HYDROGEN BONDING AND CONFORMATION OF GLUCOSE AND POLYGLUCOSES IN DIMETHYLSULPHOXIDE SOLUTION
CASU, B
REGGIANI, M
GALLO, GG
VIGEVANI, A
[J]. TETRAHEDRON, 1966, 22 (09) : 3061 - +
[10] SYNTHESIS OF CHEMICALLY MODIFIED CYCLODEXTRINS
CROFT, AP
BARTSCH, RA
[J]. TETRAHEDRON, 1983, 39 (09) : 1417 - 1474

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