Literature DB >> 21141893

Resonance stabilization energy of 1,2-azaborines: a quantitative experimental study by reaction calorimetry.

Patrick G Campbell1, Eric R Abbey, Doinita Neiner, Daniel J Grant, David A Dixon, Shih-Yuan Liu.   

Abstract

Aromatic and single-olefin six-membered BN heterocycles were synthesized, and the heats of hydrogenation were measured calorimetrically. A comparison of the hydrogenation enthalpies of these compounds revealed that 1,2-azaborines have a resonance stabilization energy of 16.6 ± 1.3 kcal/mol, in good agreement with calculated values.

Entities:  

Year:  2010        PMID： 21141893     DOI： 10.1021/ja109596m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  18 in total

Review 1.  Recent advances in azaborine chemistry.

Authors:  Patrick G Campbell; Adam J V Marwitz; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-29       Impact factor: 15.336

2.  Boron in disguise: the parent "fused" BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-07-13       Impact factor: 15.419

3.  Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine.

Authors:  Ashley N Lamm; Edward B Garner; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Photoisomerization of 1,2-dihydro-1,2-azaborine: a matrix isolation study.

Authors:  Sarah A Brough; Ashley N Lamm; Shih-Yuan Liu; Holger F Bettinger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-28       Impact factor: 15.336

5.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Authors:  Zachary X Giustra; Xinyu Yang; Min Chen; Holger F Bettinger; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

6.  UV-photoelectron spectroscopy of 1,2- and 1,3-azaborines: a combined experimental and computational electronic structure analysis.

Authors:  Anna Chrostowska; Senmiao Xu; Ashley N Lamm; Audrey Mazière; Christopher D Weber; Alain Dargelos; Patrick Baylère; Alain Graciaa; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2012-06-06       Impact factor: 15.419

7.  Rhodium-catalyzed boron arylation of 1,2-azaborines.

Authors:  Gabriel E Rudebusch; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

8.  Boron-substituted 1,3-dihydro-1,3-azaborines: synthesis, structure, and evaluation of aromaticity.

Authors:  Senmiao Xu; Tanya C Mikulas; Lev N Zakharov; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-07       Impact factor: 15.336

9.  A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.

Authors:  Steven R Wisniewski; Courtney L Guenther; O Andreea Argintaru; Gary A Molander
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

10.  BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues.

Authors:  Daniel H Knack; Jonathan L Marshall; Gregory P Harlow; Agnieszka Dudzik; Maciej Szaleniec; Shih-Yuan Liu; Johann Heider
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-28       Impact factor: 15.336
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