Enantiomeric recognition of amino acid derivatives by chiral Schiff bases of calix[4]arene

被引:40
作者
Durmaz, Mustafa [1 ]
Alpaydin, Sabri [1 ]
Sirit, Abdulkadir [1 ]
Yilmaz, Mustafa [1 ]
机构
[1] Selcuk Univ, Dept Chem, TR-42031 Konya, Turkey
关键词
D O I
10.1016/j.tetasy.2007.04.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel calix[4]arene Schiff bases bearing chiral substituents both on the upper and the lower rims have been developed. These chiral receptors exhibit good chiral recognition ability towards alpha-amino acid ester hydrochlorides (up to K-D/K-L = 4.36, Delta Delta G(O) = - 3.65 kJ mol(-1)) in CHCl3. The molecular recognition abilities and enantioselectivities for guests are also discussed from a thermodynamic point of view. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:900 / 905
页数:6
相关论文
共 30 条
[1]   Cation-pi interactions between neutral calix[5]arene hosts and cationic organic guests [J].
Arnecke, R ;
Bohmer, V ;
Cacciapaglia, R ;
Cort, AD ;
Mandolini, L .
TETRAHEDRON, 1997, 53 (13) :4901-4908
[2]   Chiral recognition of (18-crown-6)-tetracarboxylic acid as a chiral selector determined by NMR spectroscopy [J].
Bang, EJ ;
Jung, JW ;
Lee, WJ ;
Lee, DW ;
Lee, WT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (09) :1685-1692
[3]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[4]  
Diamond D, 1996, CHEM SOC REV, V25, P15, DOI 10.1039/cs9962500015
[5]   Chiral Schiff base derivatives of calix[4]arene: synthesis and complexation studies with chiral and achiral amines [J].
Durmaz, Mustafa ;
Alpaydin, Sabri ;
Sirit, Abdulkadir ;
Yilmaz, Mustafa .
TETRAHEDRON-ASYMMETRY, 2006, 17 (16) :2322-2327
[6]   Synthetic receptors for carboxylic acids and carboxylates [J].
Fitzmaurice, RJ ;
Kyne, GM ;
Douheret, D ;
Kilburn, JD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :841-864
[7]  
Gutsche C.D., 1998, CALIXARENES REVISITE
[8]  
Gutsche C.D., 1989, Calixarenes
[9]   Novel cavity design using calix[n]arene skeletons: Toward molecular recognition and metal binding [J].
Ikeda, A ;
Shinkai, S .
CHEMICAL REVIEWS, 1997, 97 (05) :1713-1734
[10]   SYNTHESES AND OPTICAL RESOLUTION OF CALIX[4]ARENES WITH MOLECULAR ASYMMETRY - SYSTEMATIC CLASSIFICATION OF ALL POSSIBLE CHIRAL ISOMERS DERIVABLE FROM CALIX[4]ARENE [J].
IWAMOTO, K ;
SHIMIZU, H ;
ARAKI, K ;
SHINKAI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3997-4006