SYMMETRY-BREAKING IN CYCLODEXTRINS - A MOLECULAR MECHANICS INVESTIGATION

被引：106
作者：
LIPKOWITZ, KB
机构：
[1] Department of Chemistry, Indiana-Purdue University, Indianapolis, Indiana 46205
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 22期
关键词：
D O I：
10.1021/jo00022a027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An analysis of the inherent features of cyclodextrins, void of water and crystal-lattice effects, has been undertaken with empirical force fields. It is found that these systems are not rigid and that symmetry breaking lowers the energies of these macrocycles. The highly symmetric structures portrayed in the literature are time-averaged views only.
引用
收藏
页码：6357 / 6367
页数：11
相关论文
共 59 条
[31]   NEW PROPERTIES OF CYCLODEXTRIN COMPLEXES IN SOLUTION AND IN SOLID-STATE [J].
LEBAS, G ;
TSOUCARIS, G .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1986, 137 (1-4) :287-301
[32]  
LIPKOWITZ KB, UNPUB J AM CHEM SOC
[33]  
LIPKOWITZ KB, 1987, QCPE B, V7, P19
[34]  
Lough W.J., 1989, CHIRAL LIQUID CHROMA
[35]   MOLECULAR MECHANICAL CALCULATION ON CYCLODEXTRIN INCLUSION COMPLEXES .1. THE STRUCTURES OF ALPHA-CYCLODEXTRIN COMPLEXES ESTIMATED BY VANDERWAALS INTERACTION ENERGY CALCULATION [J].
MATSUI, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (04) :1246-1249
[36]   DOCKING CALCULATIONS ON FERROCENE COMPLEXATION WITH CYCLODEXTRINS [J].
MENGER, FM ;
SHERROD, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (26) :8606-8611
[37]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467
[38]   A MOLECULAR MECHANICS TREATMENT OF THE ANOMERIC EFFECT [J].
NORSKOVLAURITSEN, L ;
ALLINGER, NL .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1984, 5 (04) :326-335
[39]   MOLECULAR MECHANICS STUDIES ON INCLUSION-COMPOUNDS OF CYANINE DYE MONOMERS AND DIMERS IN CYCLODEXTRIN CAVITIES [J].
OHASHI, M ;
KASATANI, K ;
SHINOHARA, H ;
SATO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5824-5830
[40]   ASYMMETRIC OSCILLATIONS IN CYCLODEXTRIN - A MOLECULAR-DYNAMICS STUDY [J].
PRABHAKARAN, M ;
HARVEY, SC .
BIOPOLYMERS, 1987, 26 (07) :1087-1096
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