Fluoride ion capture from water with a cationic borane

被引：200

作者：

Chiu, Ching-Wen ^{[1
]}

Gabbai, Francois P. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 44期

关键词：

D O I：

10.1021/ja0658463

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of the [Li(THF)4]+ salt of dimesityl-1,8-naphthalenediylborate with [Me2NCH2]I affords a borane (1-(Mes2B)-8-(Me2NCH2)-C10H6) which can be converted into a cationic borane [3]+ ([1-(Mes2B)-8-(Me3NCH2)-C10H6]+) by methylation with MeOTf. This cationic borane promptly complexes fluoride to afford the corresponding zwitterionic ammonium/fluoroborate 3-F (1-(Mes2FB)-8-(Me3NCH2)-C10H6). Cation [3]+ fails to react with chloride, bromide, and iodide indicating that fluoride complexation is selective. Structural, spectroscopic, and computational studies carried out on 3-F show the existence of an unusual C-H⋯F-B hydrogen bond. Remarkably, [3]+ captures fluoride from water under biphasic conditions (H2O/CHCl3) to form 3-F. The high fluoride affinity of [3]+ can be correlated to the Coulombic forces which stabilize the B-F bond against heterolysis. Copyright © 2006 American Chemical Society.

引用

页码：14248 / 14249

页数：2

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