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Estimated rate constants for hydrogen abstraction from n-heterocyclic carbene-borane complexes by an alkyl radical

Solovyev, A and Ueng, SH and Monot, J and Fensterbank, L and Malacria, M and Lacôte, E and Curran, DP (2010) Estimated rate constants for hydrogen abstraction from n-heterocyclic carbene-borane complexes by an alkyl radical. Organic Letters, 12 (13). 2998 - 3001. ISSN 1523-7060

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Abstract

Rate constants for hydrogen abstraction by a nonyl radical from 20 complexes of N-heterocyclic carbenes and boranes (NHC-boranes) have been determined by the pyridine-2-thioneoxycarbonyl (PTOC) competition kinetic method at a single concentration point. The rate constants range from <1 × 104 to 8 × 104 M-1 s-1. They show little dependence on the electronic properties of the carbene core, but there is a trend for increasing rate constants with decreasing size of the carbene N-substituents. Two promising new reagents with small N-substituents (R = Me) have been identified. © 2010 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Solovyev, A
Ueng, SH
Monot, J
Fensterbank, L
Malacria, M
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
Date: 2 July 2010
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 12
Number: 13
Page Range: 2998 - 3001
DOI or Unique Handle: 10.1021/ol101014q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Boranes--chemistry; Free Radicals--chemistry; Heterocyclic Compounds--chemistry; Hydrogen--chemistry; Kinetics; Methane--analogs & derivatives; Methane--chemistry; Molecular Structure; Stereoisomerism
PubMed ID: 20536158
Date Deposited: 08 Feb 2013 20:44
Last Modified: 12 Jun 2021 22:56
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/17302

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