C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method

被引：0

作者：

Aral, Hayriye ^{[1
]}

Aral, Tarik ^{[1
]}

Colak, Mehmet ^{[2
]}

Ziyadanogullari, Berrin ^{[2
]}

Ziyadanogullari, Recep ^{[2
]}

机构：

[1] Batman Univ, Fac Sci & Art, Dept Chem, Batman, Turkey

[2] Dicle Univ, Fac Sci, Dept Chem, Diyarbakir, Turkey

来源：

TURKISH JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 03期

关键词：

Enantiomeric recognition; C-2; symmetric; chiral diamines; amino acids; mandelic acid; NMR titration; PRIMARY ALKYLAMMONIUM SALTS; MOLECULAR RECOGNITION; CROWN-ETHERS; ASYMMETRIC INDUCTION; NATURAL-PRODUCTS; DERIVATIVES; 2,4,6-TRIAMINOPYRIMIDINE; INTERFACE; COMPLEXES; CONSTANTS;

D O I：

10.3906/kim-1207-58

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two novel C-2-symmetric chiral diamines containing alpha-phenylethyl and alpha-(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields. Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the H-1 NMR titration method. These ligands exhibited strong complexation (with K-f up to 2481 M-1) and good enantioselectivity (up to K-L/K-D = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic C-2-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.

引用

页码：374 / 382

页数：9

共 29 条

[1] Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts [J].

Aydin, Isil ;

Aral, Tarik ;

Karakaplan, Mehmet ;

Hosgoren, Halil .

TETRAHEDRON-ASYMMETRY, 2009, 20 (02) :179-183

[2] trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition [J].

Bennani, YL ;

Hanessian, S .

CHEMICAL REVIEWS, 1997, 97 (08) :3161-3195

[3] Molecular recognition-induced function and competitive replacement by hydrogen-bonding interactions:: Amphiphilic barbituric acid derivatives, 2,4,6-triaminopyrimidine, and related structures at the air-water interface [J].

Bohanon, TM ;

Caruso, PL ;

Denzinger, S ;

Fink, R ;

Möbius, D ;

Paulus, W ;

Preece, JA ;

Ringsdorf, H ;

Schollmeyer, D .

LANGMUIR, 1999, 15 (01) :174-184

[4] THE FORMATION OF COMPLEXES BETWEEN AZA DERIVATIVES OF CROWN ETHERS AND PRIMARY ALKYLAMMONIUM SALTS .7. CHIRAL DERIVATIVES OF AZA CROWN ETHERS [J].

CHADWICK, DJ ;

CLIFFE, IA ;

SUTHERLAND, IO ;

NEWTON, RF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1707-1717

[5] Synthesis of novel chiral Schiff-base ligands and their application in asymmetric nitro aldol (Henry) reaction [J].

Colak, Mehmet ;

Aral, Tarik ;

Hosgoeren, Halil ;

Demirel, Nadir .

TETRAHEDRON-ASYMMETRY, 2007, 18 (09) :1129-1133

[6] Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives [J].

Demirtas, Havva Nur ;

Bozkurt, Selahattin ;

Durmaz, Mustafa ;

Yilmaz, Mustafa ;

Sirit, Abdulkadir .

TETRAHEDRON, 2009, 65 (15) :3014-3018

[7] Determination of association constants (Ka) from solution NMR data [J].

Fielding, L .

TETRAHEDRON, 2000, 56 (34) :6151-6170

[8]

Fitzmaurice R. J., 2002, J CHEM SOC P1, V6, P841

[9] Effect of a hydroxyl group in an anthracene-labelled pyridine amide receptor in molecular recognition α-keto and hydroxy monocarboxylic acids [J].

Ghosh, Kumaresh ;

Masanta, Goutam .

TETRAHEDRON LETTERS, 2006, 47 (52) :9233-9237

[10] Chirality-sensing supramolecular systems [J].

Hembury, Guy A. ;

Borovkov, Victor V. ;

Inoue, Yoshihisa .

CHEMICAL REVIEWS, 2008, 108 (01) :1-73

← 1 2 3 →