Bond Strengths of Toluenes, Anilines, and Phenols: To Hammett or Not

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DOIResolve DOI: http://doi.org/10.1021/ar010010k
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TypeArticle
Journal titleAccounts of Chemical Research
ISSN0001-4842
Volume37
Issue5
Pages334340; # of pages: 7
AbstractThe Hammett equation correlates the effects of Y on many different chemical properties of YC6H4ZX families of compounds. One of the most surprising is that the Z-X bond dissociation enthalpy (BDE), a homolytic property, can be correlated for some 4-YC6H4ZX families with electrophilic substituent constants, (Y), which were largely derived from the rates of the heterolytic SN1 solvolyses of para-substituted cumyl chlorides. Although there is no Hammett correlation of the C-X BDEs in 4-YC6H4CH2X (X = H, halide, OPh) families, there are good correlations of N-X BDEs with (Y) in 4-YC6H4NHX (X = H, CH3, OH, F) and excellent correlations of O-X BDEs with (Y) in 4-YC6H4OX (X = H, CH3, CH2Ph) families. The reasons for this varied behavior are discussed.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; National Institute for Nanotechnology; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier1015128x
NPARC number12333690
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Record identifier2d92a467-2987-4555-accf-ed08f50391d5
Record created2009-09-10
Record modified2016-05-09
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