Diffusion controlled hydrogen atom abstraction from tertiary amines by the benzyloxyl radical. the importance of C-H/N hydrogen bonding

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DOIResolve DOI: http://doi.org/10.1021/ol102690u
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TypeArticle
Journal titleOrganic Letters
ISSN1523-7060
Volume13
Issue2
Pages260263; # of pages: 4
Subject1,4 cyclohexadiene; 1,4 diazabicyclo[2.2.2]octane; 1,4-cyclohexadiene; amine; benzene derivative; cyclohexene derivative; hydrogen; piperazine derivative; article; chemical model; chemical structure; chemistry; hydrogen bond; Amines; Benzene Derivatives; Cyclohexenes; Hydrogen; Hydrogen Bonding; Models, Chemical; Molecular Structure; Piperazines
AbstractThe rate constants for H-atom abstraction (k H) from 1,4-cyclohexadiene (CHD), triethylamine (TEA), triisobutylamine (TIBA), and DABCO by the cumyloxyl (CumO •) and benzyloxyl (BnO •) radicals were measured. Comparable k H values for the two radicals were obtained in their reactions with CHD and TIBA whereas large increases in k H for TEA and DABCO were found on going from CumO • to BnO •. These differences are attributed to the rate-determining formation of BnO • C-H/amine N lone-pair H-bonded complexes. © 2010 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); National Institute for Nanotechnology (NINT-INNT)
Peer reviewedYes
NPARC number21271500
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Record identifierf13198f0-1fac-416a-9664-088d99288361
Record created2014-03-24
Record modified2016-05-09
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