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

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 sp²-sp³ 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^-1. 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:	Creators Email Pitt Username ORCID Damodaran, K Li, X Pan, X Curran, DP curran@pitt.edu CURRAN
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:	10 Apr 2021 22:55
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/25651

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