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Titolo:
Studies on molecular recognition in supramolecular systems. Part 31: Circular dichroism spectral studies of molecular and chiral recognition of aliphatic alcohols by 6-modified beta-cyclodextrins
Autore:
Liu, Y; Li, B; Wada, T; Inoue, Y;
Indirizzi:
Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China Nankai Univ Tianjin Peoples R China 300071 anjin 300071, Peoples R China JST, ERATO, Inoue Photochirogenesis Project, Toyonaka, Osaka 5650085, Japan JST Toyonaka Osaka Japan 5650085 Project, Toyonaka, Osaka 5650085, Japan Osaka Univ, Dept Mol Chem, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 ol Chem, Suita, Osaka 5650871, Japan
Titolo Testata:
TETRAHEDRON
fascicolo: 33, volume: 57, anno: 2001,
pagine: 7153 - 7161
SICI:
0040-4020(20010813)57:33<7153:SOMRIS>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
INCLUSION COMPLEXATION; ALPHA-CYCLODEXTRIN; ENANTIOSELECTIVE RECOGNITION; FLUORESCENT CYCLODEXTRINS; NAPHTHALENE DERIVATIVES; DENDRITIC RECEPTORS; AQUEOUS-SOLUTION; L-TRYPTOPHAN; AMINO-ACIDS; BINDING;
Keywords:
molecular recognition; cyclodetrins; circular dichroism;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
41
Recensione:
Indirizzi per estratti:
Indirizzo: Liu, Y Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China Nankai Univ Tianjin Peoples R China 300071 00071, Peoples R China
Citazione:
Y. Liu et al., "Studies on molecular recognition in supramolecular systems. Part 31: Circular dichroism spectral studies of molecular and chiral recognition of aliphatic alcohols by 6-modified beta-cyclodextrins", TETRAHEDRON, 57(33), 2001, pp. 7153-7161

Abstract

The stability constants (Ks) for the inclusion complexation of novel mono[6-O-(1- benzotriazole)]-beta -cyclodextrin (2) and mono (6-benzylseleno-6-deoxy)-beta -cyclodextrin (3) with a series of chiral and achiral (cyclo)alkanols have been determined at 25 degreesC in aqueous phosphate buffer solution at pH 7.20 by circular dichroism spectral titration. It was revealed that 2 and 3 can fairly strictly recognize not only the size/shape but also the chirality of guest molecules. Thus, the log Ks value, or the Gibbs free energy change increases linearly with increasing number of carbon atoms (Nc) in cycloalkanol, affording comparable increments per methylene unit: -d DeltaG(0)/dN(C)=2.0 and 2.2 kJ mol(-1) for 2 and 3, respectively. Furthermore, 2 and 3 displayed moderate to excellent isomer selectivities of up to 15.3 for the guest alcohols examined, while moderate enantioselectivities of 1.1-1.4 were obtained with chiral borneol and menthol guests upon complexation with 2 and 3. The present results obtained with 2 and 3 elucidate the effects of substituents on the complexation behavior as well as some of the factors governing size, shape, and chiral selectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/07/20 alle ore 17:42:35