1,2-BN Cyclohexane: Synthesis, Structure, Dynamics, and Reactivity

被引：91

作者：

Luo, Wei ^{[1
]}

Zakharov, Lev N. ^{[1
]}

Liu, Shih-Yuan ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 33期

关键词：

HYDROGEN STORAGE; B-N; C-C; BORON; AMMONIA; BORANE; HYDROBORATION; DIVERSITY; ANALOGS; AMINE;

D O I：

10.1021/ja206497x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

BN/CC isosterism has emerged as a viable strategy to increase the structural diversity of carbon-based compounds. We present the first synthesis and characterization of the parent 1,2-BN cyclohexane, the BN-isostere of cyclohexane. 1,2-BN cyclohexane is an air- and water-stable compound that cleanly forms a trimer with release of dihydrogen when thermally activated. We also demonstrate that 1,2-BN cyclohexane has a lower activation barrier for ring inversion than cyclohexane due to BN/CC isosterism.

引用

收藏

页码：13006 / 13009

页数：4

相关论文

共 44 条

[1] Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines [J].

Abbey, Eric R. ;

Zakharov, Lev N. ;

Liu, Shih-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7250-+

[2] Electrophilic Aromatic Substitution of a BN Indole [J].

Abbey, Eric R. ;

Zakharov, Lev N. ;

Liu, Shih-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16340-16342

[3]

Anslyn E.V., 2006, MODERN PHYS ORGANIC, P102

[4] B-N as a C-C substitute in aromatic systems [J].

Bosdet, Michael J. D. ;

Piers, Warren E. .

CANADIAN JOURNAL OF CHEMISTRY, 2009, 87 (01) :8-29

[5] SOLVATION EFFECTS ON GEOMETRY AND CHEMICAL-SHIFTS - AN ABINITIO IGLO RECONCILIATION OF APPARENT EXPERIMENTAL INCONSISTENCIES ON H3B.NH3 [J].

BUHL, M ;

STEINKE, T ;

SCHLEYER, PV ;

BOESE, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (09) :1160-1161

[6] Resonance Stabilization Energy of 1,2-Azaborines: A Quantitative Experimental Study by Reaction Calorimetry [J].

Campbell, Patrick G. ;

Abbey, Eric R. ;

Neiner, Doinita ;

Grant, Daniel J. ;

Dixon, David A. ;

Liu, Shih-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) :18048-18050

[7] Hydrogen Storage by Boron-Nitrogen Heterocycles: A Simple Route for Spent Fuel Regeneration [J].

Campbell, Patrick G. ;

Zakharov, Lev N. ;

Grant, Daniel J. ;

Dixon, David A. ;

Liu, Shih-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3289-+

[8] BORON-NITRIDE NANOTUBES [J].

CHOPRA, NG ;

LUYKEN, RJ ;

CHERREY, K ;

CRESPI, VH ;

COHEN, ML ;

LOUIE, SG ;

ZETTL, A .

SCIENCE, 1995, 269 (5226) :966-967

[9] Microwave Spectrum, Structural Parameters, and Quadrupole Coupling for 1,2-Dihydro-1,2-azaborine [J].

Daly, Adam M. ;

Tanjaroon, Chakree ;

Marwitz, Adam J. V. ;

Liu, Shih-Yuan ;

Kukolich, Stephen G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5501-5506

[10]

Eliel E. L., 1994, STEREOCHEMISTRY ORGA

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