CIRCULAR-DICHROISM OF METHYLATED PHENOLS INCLUDED IN BETA-CYCLODEXTRIN - AN EXPERIMENTAL AND THEORETICAL-STUDY

被引：51

作者：

MARCONI, G ^{[1
]}

MONTI, S ^{[1
]}

MAYER, B ^{[1
]}

KOHLER, G ^{[1
]}

机构：

[1] UNIV VIENNA,INST THEORET CHEM & STRAHLENCHEM,A-1090 VIENNA,AUSTRIA

来源：

JOURNAL OF PHYSICAL CHEMISTRY | 1995年 / 99卷 / 12期

关键词：

D O I：

10.1021/j100012a013

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The rotatory strength of inclusion complexes of various methyl-substituted phenols (phenol, p-cresol, 2,6- and 3,5-dimethyl-, and 2,4,6- and 3,4,5-trimethylphenol) with beta-cyclodextrin are calculated by a combination of molecular mechanics and semiempirical methods, and the results are compared to the respective experimentally induced circular dichroism spectra. In general, experimental results are nicely reproduced, although symmetry breaking in the cyclodextrin, i.e. deviation from the ideally truncated cone-shaped structure, and the conformational flexibility of the complexes contribute essentially to sign and strength of the induced circular dichroism.

引用

页码：3943 / 3950

页数：8

共 28 条

[1]

Allinger N., 1989, J AM CHEM SOC, V111, P8551, DOI 10.1021/ja00205a001,10.1021/ja00205a002

[2] MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].

ALLINGER, NL ;

YUH, YH ;

LII, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566

[3]

ALLINGER NL, 1989, QCPE B, V9, P2

[4]

ALLINGER NL, 1989, J AM CHEM SOC, V111, P8566

[5]

Bender M. L., 1978, CYCLODEXTRIN CHEM, DOI [10.1007/978-3-642-66842-5, DOI 10.1007/978-3-642-66842-5]

[6] SUBSTITUENT EFFECTS ON THE BINDING OF PHENOLS TO CYCLODEXTRINS IN AQUEOUS-SOLUTION [J].

BERTRAND, GL ;

FAULKNER, JR ;

HAN, SM ;

ARMSTRONG, DW .

JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (18) :6863-6867

[7] TOPOGRAPHY OF CYCLODEXTRIN INCLUSION COMPLEXES .20. CIRCULAR AND FLIP-FLOP HYDROGEN-BONDING IN BETA-CYCLODEXTRIN UNDECAHYDRATE - A NEUTRON-DIFFRACTION STUDY [J].

BETZEL, C ;

SAENGER, W ;

HINGERTY, BE ;

BROWN, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7545-7557

[8] COMPLEX-FORMATION OF PHENOL, ANILINE, AND THEIR NITRO-DERIVATIVES WITH BETA-CYCLODEXTRIN [J].

BUVARI, A ;

BARCZA, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (04) :543-545

[9] MINIATURE ORGANIC-MODELS OF ENZYMES [J].

DSOUZA, VT ;

BENDER, ML .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (04) :146-152

[10] PICOSECOND LASER STUDIES ON PHOTOCHEMICAL-REACTIONS IN RESTRICTED ENVIRONMENTS - THE PHOTOISOMERIZATION OF TRANS-STILBENE COMPLEXED TO CYCLODEXTRINS [J].

DUVENECK, GL ;

SITZMANN, EV ;

EISENTHAL, KB ;

TURRO, NJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (20) :7166-7170

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