Molecular recognition and stabilization of iminium ions in water

被引：182

作者：

Dong, Vy M. ^{[1
]}

Fiedler, Dorothea ^{[1
]}

Carl, Barbara ^{[1
]}

Bergman, Robert G. ^{[1
]}

Raymond, Kenneth N. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 45期

关键词：

D O I：

10.1021/ja0657915

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iminium ions are known to exist only transiently in aqueous solution due to their high reactivity toward hydrolysis. In this communication, we report on the generation and stabilization of iminium ions in aqueous solution via molecular encapsulation using a K12Ga4L6 host. Our studies revealed that tetrahedral host 1 can encapsulate a variety of iminium cations in a molecular recognition process that is selective based on the charge, hydrophobicity, size, and shape of the guest. Copyright © 2006 American Chemical Society.

引用

页码：14464 / 14465

页数：2

共 17 条

[1]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[2]

Bohme H., 1976, IMINIUM SALTS ORGANI, P145

[3] Encapsulation and stabilization of reactive aromatic diazonium ions and the tropylium ion within a supramolecular host [J].

Brumaghim, JL ;

Michels, M ;

Pagliero, D ;

Raymond, KN .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (24) :5115-5118

[4] Hydrophobic chemistry in aqueous solution: Stabilization and stereoselective encapsulation of phosphonium guests in a supramolecular host [J].

Brumaghim, JL ;

Michels, M ;

Raymond, KN .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (22) :4552-4559

[5] Coordination number incommensurate cluster formation, part 21 -: Design, formation and properties of tetrahedral M4L4 and M4L6 supramolecular clusters [J].

Caulder, DL ;

Brückner, C ;

Powers, RE ;

König, S ;

Parac, TN ;

Leary, JA ;

Raymond, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :8923-8938

[6] LIFETIME OF AN ALIPHATIC IMINIUM ION IN AQUEOUS-SOLUTION [J].

ELDIN, S ;

DIGITS, JA ;

HUANG, ST ;

JENCKS, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6631-6632

[7] Stabilization of reactive organometallic intermediates inside a self-assembled nanoscale host [J].

Fiedler, D ;

Bergman, RG ;

Raymond, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (05) :745-748

[8] Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels [J].

Fiedler, D ;

Leung, DH ;

Bergman, RG ;

Raymond, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (04) :349-358

[9] Virtual combinatorial libraries: Dynamic generation of molecular and supramolecular diversity by self-assembly [J].

Huc, I ;

Lehn, JM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (06) :2106-2110

[10]

Jencks W.P., 1987, CATALYSIS CHEM ENZYM

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