Generation and structure of unique boriranyl radicals

John C. Walton; Timothy R. McFadden; Dennis P. Curran

doi:10.1021/jacs.7b10788

Generation and structure of unique boriranyl radicals

John C. Walton^*, Timothy R. McFadden, Dennis P. Curran^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Three-member ring boracyclopropanes (boriranes) with N-heterocyclic carbene substituents were prepared by a recently discovered route. H atoms were selectively abstracted from the boron atoms by t-butoxyl radicals and this enabled boriranyl radicals to be detected and characterized by EPR spectroscopy for the first time. Their EPR parameters indicated they had planar π-character. From competition experiments, the rate constant for H atom abstraction was determined and found to be about 2 orders of magnitude less than for NHC-boranes. The B–H BDE of an NHC-borirane was estimated to be about 95 kcal mol^–1.

Original language	English
Pages (from-to)	16514-16517
Journal	Journal of the American Chemical Society
Volume	139
Issue number	46
Early online date	3 Nov 2017
DOIs	https://doi.org/10.1021/jacs.7b10788
Publication status	Published - 22 Nov 2017

Access to Document

10.1021/jacs.7b10788

BoriraneRadJACSRevisedNov3
Copyright © 2017 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/jacs.7b10788
Accepted author manuscript, 159 KB

Cite this

@article{a4049074b1f14f8796038cb4aef8e5e9,

title = "Generation and structure of unique boriranyl radicals",

abstract = "Three-member ring boracyclopropanes (boriranes) with N-heterocyclic carbene substituents were prepared by a recently discovered route. H atoms were selectively abstracted from the boron atoms by t-butoxyl radicals and this enabled boriranyl radicals to be detected and characterized by EPR spectroscopy for the first time. Their EPR parameters indicated they had planar π-character. From competition experiments, the rate constant for H atom abstraction was determined and found to be about 2 orders of magnitude less than for NHC-boranes. The B–H BDE of an NHC-borirane was estimated to be about 95 kcal mol–1.",

author = "Walton, \{John C.\} and McFadden, \{Timothy R.\} and Curran, \{Dennis P.\}",

note = "J.C.W. thanks EaStCHEM for financial support. T.R.M. and D.P.C. thank the US National Science Foundation for grant CHE-1660927.",

year = "2017",

month = nov,

day = "22",

doi = "10.1021/jacs.7b10788",

language = "English",

volume = "139",

pages = "16514--16517",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society (ACS)",

number = "46",

}

TY - JOUR

T1 - Generation and structure of unique boriranyl radicals

AU - Walton, John C.

AU - McFadden, Timothy R.

AU - Curran, Dennis P.

N1 - J.C.W. thanks EaStCHEM for financial support. T.R.M. and D.P.C. thank the US National Science Foundation for grant CHE-1660927.

PY - 2017/11/22

Y1 - 2017/11/22

N2 - Three-member ring boracyclopropanes (boriranes) with N-heterocyclic carbene substituents were prepared by a recently discovered route. H atoms were selectively abstracted from the boron atoms by t-butoxyl radicals and this enabled boriranyl radicals to be detected and characterized by EPR spectroscopy for the first time. Their EPR parameters indicated they had planar π-character. From competition experiments, the rate constant for H atom abstraction was determined and found to be about 2 orders of magnitude less than for NHC-boranes. The B–H BDE of an NHC-borirane was estimated to be about 95 kcal mol–1.

AB - Three-member ring boracyclopropanes (boriranes) with N-heterocyclic carbene substituents were prepared by a recently discovered route. H atoms were selectively abstracted from the boron atoms by t-butoxyl radicals and this enabled boriranyl radicals to be detected and characterized by EPR spectroscopy for the first time. Their EPR parameters indicated they had planar π-character. From competition experiments, the rate constant for H atom abstraction was determined and found to be about 2 orders of magnitude less than for NHC-boranes. The B–H BDE of an NHC-borirane was estimated to be about 95 kcal mol–1.

UR - https://www.scopus.com/pages/publications/85034970775

U2 - 10.1021/jacs.7b10788

DO - 10.1021/jacs.7b10788

M3 - Article

SN - 0002-7863

VL - 139

SP - 16514

EP - 16517

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

ER -

Generation and structure of unique boriranyl radicals

Abstract

Access to Document

Other files and links

Fingerprint

John Walton

Cite this

Generation and structure of unique boriranyl radicals

Abstract

Access to Document

Other files and links

Fingerprint

Profiles

John Walton

Cite this