On the Importance of the Aromatic Ring Parameter in Studies of the Solvolyses of Cinnamyl and Cinnamoyl Halides
Joint Authors
D'Souza, Malcolm J.
Kevill, Dennis N.
Darrington, Anthony M.
Source
Organic Chemistry International
Issue
Vol. 2010, Issue 2010 (31 Dec. 2010), pp.1-9, 9 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2010-06-29
Country of Publication
Egypt
No. of Pages
9
Main Subjects
Abstract EN
In solvolysis studies using Grunwald-Winstein plots, dispersions were observed for substrates with aromatic rings at the α-carbon.
Several examples for the unimolecular solvolysis of monoaryl benzylic derivatives and related diaryl- or naphthyl-substituted derivatives have now been reported, where the application of the aromatic ring parameter (I) removes this dispersion.
A recent claim suggesting the presence of an appreciable nucleophilic component to the I scale has now been shown, in a review of the solvolysis of highly-hindered alkyl halides, to be unlikely to be correct.
Attention is now focused on the application of the hI term for the solvolysis of compounds containing a double bond in the vicinity of any developing carbocation.
Available specific rates of solvolysis (plus some new values) at 25°C of cinnamyl chloride, cinnamyl bromide, cinnamoyl chloride, p-chlorocinnamoyl chloride, and p-nitrocinnamoyl chloride are analyzed using the simple and extended (including the hI term) Grunwald-Winstein equations.
American Psychological Association (APA)
D'Souza, Malcolm J.& Darrington, Anthony M.& Kevill, Dennis N.. 2010. On the Importance of the Aromatic Ring Parameter in Studies of the Solvolyses of Cinnamyl and Cinnamoyl Halides. Organic Chemistry International،Vol. 2010, no. 2010, pp.1-9.
https://search.emarefa.net/detail/BIM-448085
Modern Language Association (MLA)
D'Souza, Malcolm J.…[et al.]. On the Importance of the Aromatic Ring Parameter in Studies of the Solvolyses of Cinnamyl and Cinnamoyl Halides. Organic Chemistry International No. 2010 (2010), pp.1-9.
https://search.emarefa.net/detail/BIM-448085
American Medical Association (AMA)
D'Souza, Malcolm J.& Darrington, Anthony M.& Kevill, Dennis N.. On the Importance of the Aromatic Ring Parameter in Studies of the Solvolyses of Cinnamyl and Cinnamoyl Halides. Organic Chemistry International. 2010. Vol. 2010, no. 2010, pp.1-9.
https://search.emarefa.net/detail/BIM-448085
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-448085