Lewis Acidity Enhancement of Triarylboranes via Peripheral Decoration with Cationic Groups

被引:122
作者
Chiu, Ching-Wen [1 ]
Kim, Youngmin [1 ]
Gabbai, Francois P. [1 ]
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
基金
美国国家科学基金会;
关键词
FLUORIDE-ION; BORANES; CYANIDE; WATER; TRIS(PENTAFLUOROPHENYL)BORANE; COMPLEXATION;
D O I
10.1021/ja808572t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cationic boranes [ArN+BMeS2](+), [Ar2N+BMeS](2+), and [Ar3N+B](3+) (ArN+ = [4-(Me3N)-2,6-Me-2-C6H2](+); Mes = mesityl) have been synthesized and studied by cyclic voltammetry. The results obtained in this study show that the reduction potential of these derivatives in THF is increased by 0.36 V upon each substitution of a mesityl by a cationic ArN+ anilium group. Remarkably, the trication [3](3+), whose triflate salt is water soluble, complexes cyanide anions in pure water at pH 7. These properties underscore the dramatic effects caused by the increased number of cationic groups.
引用
收藏
页码:60 / +
页数:3
相关论文
共 24 条
[1]   Phase transfer of fluoride ion by phosphonioborins [J].
Agou, Tomohiro ;
Kobayashi, Junji ;
Kim, Youngmin ;
Gabbai, Franqois P. ;
Kawashima, Takayuki .
CHEMISTRY LETTERS, 2007, 36 (08) :976-977
[2]   Tuning of the optical properties and Lewis acidity of dibenzopnictogenaborins by modification on bridging main group elements [J].
Agou, Tomohiro ;
Kobayashi, Junji ;
Kawashima, Takayuki .
INORGANIC CHEMISTRY, 2006, 45 (22) :9137-9144
[3]   Cocatalysts for metal-catalyzed olefin polymerization: Activators, activation processes, and structure-activity relationships [J].
Chen, EYX ;
Marks, TJ .
CHEMICAL REVIEWS, 2000, 100 (04) :1391-1434
[4]   Diarylborenium cations: Synthesis, structure, and electrochemistry [J].
Chiu, Ching-Wen ;
Gabbai, Francois P. .
ORGANOMETALLICS, 2008, 27 (07) :1657-1659
[5]   Fluoride ion capture from water with a cationic borane [J].
Chiu, Ching-Wen ;
Gabbai, Francois P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) :14248-14249
[6]   The benzil-cyanide reaction and its application to the development of a selective cyanide anion indicator [J].
Cho, Dong-Gyu ;
Kim, Jong Hoon ;
Sessler, Jonathan L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :12163-12167
[7]   An estimate of the reduction potential of B(C6F5)3 from electrochemical measurements on related mesityl boranes [J].
Cummings, SA ;
Iimura, M ;
Harlan, CJ ;
Kwaan, RJ ;
Trieu, IV ;
Norton, JR ;
Bridgewater, BM ;
Jäkle, F ;
Sundararaman, A ;
Tilset, M .
ORGANOMETALLICS, 2006, 25 (07) :1565-1568
[8]   Colorimetric fluoride ion sensing by polyborylated ferrocenes: Structural influences on thermodynamics and kinetics [J].
Day, Joanna K. ;
Bresner, Christopher ;
Coombs, Natalie D. ;
Fallis, Ian A. ;
Ooi, Li-Ling ;
Aldridge, Simon .
INORGANIC CHEMISTRY, 2008, 47 (03) :793-804
[9]  
Dusemund C., 1995, CHEM COMMUN, P333
[10]   Metal pi complexes of benzene derivatives .49. Halfsandwich complexes of trimesitylborane Mes(3)B: Synthesis and structure of Mes(2)[B(eta(6)-Mes)Cr(CO)(3)], MesB[eta(6)-MesCr(CO)(3)](2), and B[eta(6)-MesCr(CO)(3)](3). Redox behavior and questions of intramolecular interaction [J].
Elschenbroich, C ;
Kuhlkamp, P ;
Behrendt, A ;
Harms, K .
CHEMISCHE BERICHTE, 1996, 129 (07) :859-869