Enantioselectivity in gas-phase ion-molecule reactions

被引:89
作者
Speranza, M [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy
关键词
gas-phase enantioselectivity; noncovalent interactions; mass spectrometry; radiolysis;
D O I
10.1016/j.ijms.2004.02.008
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
Comprehensive understanding of information transfer between chiral molecules in living systems and in supramolecular assemblies requires the quantitative determination of the intrinsic short-range forces controlling enantioselectivity in simplified models, such as diastereomeric ion-molecule complexes in the isolated state. This review article describes the state-of-art in this field. Emphasis is put on the generation of diastereomeric ion-molecule aggregates in the gas phase and the determination of their relative stability and reactivity by mass spectrometric and radiolytic techniques. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:277 / 317
页数:41
相关论文
共 198 条
[1]   Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase? [J].
Ahn, S ;
Ramirez, J ;
Grigorean, G ;
Lebrilla, CB .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2001, 12 (03) :278-287
[2]   GAS-PHASE ACID-INDUCED NUCLEOPHILIC DISPLACEMENT-REACTIONS .5. QUANTITATIVE-EVALUATION OF NEIGHBORING-GROUP PARTICIPATION IN BIFUNCTIONAL COMPOUNDS [J].
ANGELINI, G ;
SPERANZA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3800-3806
[3]   GAS-PHASE ACID-INDUCED NUCLEOPHILIC DISPLACEMENT-REACTIONS .4. A STEREOCHEMICAL PROBE FOR THE EXISTENCE AND THE RELATIVE STABILITY OF CYCLIC HALONIUM IONS IN THE GAS-PHASE [J].
ANGELINI, G ;
SPERANZA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3792-3799
[4]  
ANGELINI G, 1978, CHEM COMMUN, V5, P213
[5]   Entropy measurements and the kinetic method: A statistically meaningful approach [J].
Armentrout, PB .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2000, 11 (05) :371-379
[6]   Probing gaseous ion-molecule complexes with chiral agents: The reaction of arenium ions with (R)-(-)-s-butyl chloride [J].
Aschi, M ;
Cacace, F ;
Troiani, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :83-85
[7]   Quantitative determination of the enantiomeric composition of thalidomide solutions by electrospray ionization tandem mass spectrometry [J].
Augusti, DV ;
Augusti, R ;
Carazza, F ;
Cooks, RG .
CHEMICAL COMMUNICATIONS, 2002, (19) :2242-2243
[8]   IDENTIFICATION OF CHIRAL ISOMERS BY FAST ATOM BOMBARDMENT MASS-SPECTROMETRY - DIALKYL TARTRATES [J].
BALDWIN, MA ;
HOWELL, SA ;
WELHAM, KJ ;
WINKLER, FJ .
BIOMEDICAL AND ENVIRONMENTAL MASS SPECTROMETRY, 1988, 16 (1-12) :357-360
[9]  
BENILEY TW, 1979, J AM CHEM SOC, V101, P2486
[10]   THE SN2-SN1 SPECTRUM .3. SOLVOLYSES OF SECONDARY AND TERTIARY ALKYL SULFONATES IN FLUORINATED ALCOHOLS - FURTHER EVIDENCE FOR THE SN2 (INTERMEDIATE) MECHANISM [J].
BENTLEY, TW ;
BOWEN, CT ;
MORTEN, DH ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5466-5475