Molecular mousetraps: Gas-phase studies of the covalent coupling of noncovalent complexes initiated by reactive carbenes formed by controlled activation of diazo precursors

被引：31

作者：

Julian, RR

May, JA

Stoltz, BM ^{[1
]}

Beauchamp, JL

机构：

[1] CALTECH, Beckman Inst, Pasadena, CA 91125 USA

[2] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 09期

关键词：

D O I：

10.1002/anie.200390258

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The covalent linking of noncovalently bound host-guest complexes in the gas phase is achieved by the formation of a highly reactive carbene from the host molecule, which is generated by collision-activated dissociation. Possible mechanisms for the resulting intermolecular reactions are explored by theory and experiment.

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页码：1012 / +

页数：5

相关论文

共 31 条

[1]

Beer P. D., 1999, SUPRAMOLECULAR CHEM

[2] Mass spectrometric detection of reactive intermediates. Reaction mechanism of diazoalkanes with platinum(0) and gold(I) complexes [J].

Bertani, R ;

Michelin, RA ;

Mozzon, M ;

Traldi, P ;

Seraglia, R ;

Busetto, L ;

Cassani, MC ;

Tagliatesta, P ;

DArcangelo, G .

ORGANOMETALLICS, 1997, 16 (14) :3229-3233

[3]

Bradshaw J.S., 1996, COMPREHENSIVE SUPRAM, V1, P35

[4] Intrinsic contributions to chiral recognition: Discrimination between enantiomeric amines by dimethyldiketopyridino-18-crown-6 in the gas phase [J].

Dearden, DV ;

Dejsupa, C ;

Liang, YJ ;

Bradshaw, JS ;

Izatt, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (02) :353-359

[5]

Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

[6] Characterization of ionized carbenes in the gas phase [J].

Flammang, R ;

Nguyen, MT ;

Bouchoux, G ;

Gerbaux, P .

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2000, 202 (1-3) :A8-A26

[7] COLLISION-INDUCED DISSOCIATION [J].

HAYES, RN ;

GROSS, ML .

METHODS IN ENZYMOLOGY, 1990, 193 :237-263

[8] BAKERIAN LECTURE - SPECTRA AND STRUCTURES OF FREE METHYL AND FREE METHYLENE [J].

HERZBERG, G .

PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1961, 262 (1310) :291-+

[9] Site specific sequestering and stabilization of charge in peptides by supramolecular adduct formation with 18-crown-6 ether by way of electrospray ionization [J].

Julian, RR ;

Beauchamp, JL .

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2001, 210 (1-3) :613-623

[10] Selective binding of crown ethers to protonated peptides can be used to probe mechanisms of H/D exchange and collision-induced dissociation reactions in the gas phase [J].

Lee, SW ;

Lee, HN ;

Kim, HS ;

Beauchamp, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5800-5805

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