Host-Guest Hydrogen Atom Transfer Induced by Electron Capture

被引:6
作者
Hao, Changtong [1 ]
Turecek, Frantisek [1 ]
机构
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
基金
美国国家科学基金会;
关键词
IONIZATION MASS-SPECTROMETRY; ION-CYCLOTRON RESONANCE; CROWN ETHER COMPLEXES; AMINO ACID COMPLEXES; GAS-PHASE; INCLUSION COMPLEXES; BETA-CYCLODEXTRIN; UNIMOLECULAR REACTIVITY; NONCOVALENT COMPLEXES; MOLECULAR RECOGNITION;
D O I
10.1016/j.jasms.2008.12.001
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
1,n-Alkanediammonium cations in noncovalent complexes with two dibenzo-18-crown-6-ether (DBCE) ligands undergo an unusual intramolecular tandem hydrogen atom and proton transfer to the crown ether ligand upon charge reduction by electron capture. Deuterium labeling established that both migrating hydrogens originated from the ammonium groups. The double hydrogen transfer was found to depend on the length of the alkane chain connecting the ammonium groups. Ab initio calculations provided structures for select alkanediammonium.dibenzo-18-crown-6-ether complexes and dissociation products. This first observation of an intra-complex hydrogen transfer is explained by the unusual electronic properties of the complexes and the substantial hydrogen atom affinity of the aromatic rings in the crown ligand. (J Am Soc Mass Spectrom 2009, 20, 639-651) (C) 2009 Published by Elsevier Inc. on behalf of American Society for Mass Spectrometry
引用
收藏
页码:639 / 651
页数:13
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