Absolute rate constants of alkene addition reactions of a fluorinated radical in water

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DOIResolve DOI: http://doi.org/10.1021/ja0256010
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume124
Issue22
Pages63626366; # of pages: 5
SubjectLaser flash photolysis; Laser beams; Olefins; Organic solvents; Photolysis; Solubility; Rate constants; alkene; fluorine; solvent; article; fluorination; molecular stability; photolysis; polarization; reaction analysis; solubility; structure analysis
AbstractAbsolute rate constants of ·RfSO3 -radical addition to a series of water-soluble alkenes containing ionic, carboxylate substituents were measured by laser flash photolysis experiments in water. The observed rate constants were all considerably larger than those of structurally similar analogues in a nonpolar organic solvent, with rate factors of 3-9-fold being observed. It is concluded that such rate enhancements derive at least in part from stabilization of the polar transition state for addition of the electrophilic fluorinated radical to alkenes by the polar solvent water.
Publication date
PublisherAmerican Chemical Society
LanguageEnglish
AffiliationNational Research Council Canada
Peer reviewedYes
NPARC number21276758
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Record identifier124c64aa-fb51-4827-94c3-18efb61397d2
Record created2015-10-13
Record modified2017-03-10
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