Molecular recognition of alkylammonium contact ion-pairs using a ditopic receptor

被引：62

作者：

Mahoney, JM ^{[1
]}

Davis, JP ^{[1
]}

Beatty, AM ^{[1
]}

Smith, BD ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo035270p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ditopic, macrobicyclic receptor with adjacent anion and cation binding sites is able to distinguish between various monoalkylammonium salts by binding them as contact ion-pairs. The affinity for linear n-propylammonium chloride is at least 2 orders of magnitude greater than that for n-propylammonium. acetate, n-propylammonium p-toluenesulfonate, and branched isopropylammonium chloride. An X-ray structure of the receptor complexed with methylammonium chloride illuminates the basis of the molecular recognition.

引用

页码：9819 / 9820

页数：2

共 36 条

[1] Anion allosteric effect in the recognition of tetramethylammonium salts by calix[4]arene cone conformers [J].

Arduini, A ;

Giorgi, G ;

Pochini, A ;

Secchi, A ;

Ugozzoli, F .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8302-8308

[2] Anion effects on the recognition of ion pairs by calix[4]arene-based heteroditopic receptors [J].

Arduini, A ;

Brindani, E ;

Giorgi, G ;

Pochini, A ;

Secchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6188-6194

[3] Functionalized derivatives of benzocrown-ethers, V - Multiple molecular recognition of zwitterionic phenylalanine [J].

Barboiu, M ;

Hovnanians, ND ;

Luca, C ;

Cot, L .

TETRAHEDRON, 1999, 55 (30) :9221-9232

[4] Electrostatic attraction of counterion dominates the cation-π interaction of acetylcholine and tetramethylammonium with aromatics in chloroform [J].

Bartoli, S ;

Roelens, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) :11908-11909

[5]

Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO

[6]

2-G

[7] Counteranion effect on complexation of quats by a neutral calix[5]arene receptor [J].

Böhmer, V ;

Dalla Cort, A ;

Mandolini, L .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1900-1902

[8] Recognition and binding of paraquat dichloride by cyclodextrin/calix[6]pyrrole binary host systems [J].

Cafeo, G ;

Gargiulli, C ;

Gattuso, G ;

Kohnke, FH ;

Notti, A ;

Occhipinti, S ;

Pappalardo, S ;

Parisi, MF .

TETRAHEDRON LETTERS, 2002, 43 (45) :8103-8106

[9]

Cafeo G, 2002, ANGEW CHEM INT EDIT, V41, P2122, DOI 10.1002/1521-3773(20020617)41:12<2122::AID-ANIE2122>3.0.CO

[10]

2-U

← 1 2 3 4 →