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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
5
pubmed:dateCreated
2004-5-18
pubmed:abstractText
The Hammett equation correlates the effects of Y on many different chemical properties of YC(6)H(4)ZX 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-YC(6)H(4)ZX families with electrophilic substituent constants, sigma(p)(+)(Y), which were largely derived from the rates of the heterolytic S(N)1 solvolyses of para-substituted cumyl chlorides. Although there is no Hammett correlation of the C-X BDEs in 4-YC(6)H(4)CH(2)X (X = H, halide, OPh) families, there are good correlations of N-X BDEs with sigma(p)(+)(Y) in 4-YC(6)H(4)NHX (X = H, CH(3), OH, F) and excellent correlations of O-X BDEs with sigma(p)(+)(Y) in 4-YC(6)H(4)OX (X = H, CH(3), CH(2)Ph) families. The reasons for this varied behavior are discussed.
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
May
pubmed:issn
0001-4842
pubmed:author
pubmed:issnType
Print
pubmed:volume
37
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
334-40
pubmed:year
2004
pubmed:articleTitle
Bond strengths of toluenes, anilines, and phenols: to hammett or not.
pubmed:affiliation
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
pubmed:publicationType
Journal Article