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Dynamic behavior of N-heterocyclic carbene boranes: Boron-carbene bonds in B, B -disubstituted N, N -dimethylimidazol-2-ylidene boranes have substantial rotation barriers

Damodaran, K and Li, X and Pan, X and Curran, DP (2015) Dynamic behavior of N-heterocyclic carbene boranes: Boron-carbene bonds in B, B -disubstituted N, N -dimethylimidazol-2-ylidene boranes have substantial rotation barriers. Journal of Organic Chemistry, 80 (9). 4465 - 4469. ISSN 0022-3263

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Abstract

© 2015 American Chemical Society. Dynamic NMR spectroscopy has been used to measure rotation barriers in five B,B-disubstituted 1,3-dimethylimidazol-2-ylidene boranes. The barriers are attributed to the sp<sup>2</sup>-sp<sup>3</sup> bond between C(1) of the N-heterocyclic carbene ring and the boron atom. Bonds to boron atoms bearing a thexyl (1,1,2-trimethylpropyl) group show especially high barriers, ranging from 75-86 kJ mol<sup>-1</sup>. 2-Isopropyl-1,3,5-trimethylbenzene is used as a comparable to help understand the nature and magnitude of the barriers.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Damodaran, K
Li, X
Pan, X
Curran, DPcurran@pitt.eduCURRAN
Date: 1 May 2015
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 80
Number: 9
Page Range: 4465 - 4469
DOI or Unique Handle: 10.1021/acs.joc.5b00324
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
PubMed ID: 25843519
Date Deposited: 17 Jul 2015 20:09
Last Modified: 02 Feb 2019 13:55
URI: http://d-scholarship.pitt.edu/id/eprint/25651

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