European Journal of Chemistry

Correlation of the rates of solvolysis of α-bromoisobutyrophenone using both simple and extended forms of the Grunwald-Winstein equation and the application of correlation analysis to related studies

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Published: Mar 31, 2018
DOI: https://doi.org/10.5155/eurjchem.9.1.1-6.1680
Keywords:
Solvolysis, Mechanism, Correlation, α-Bromoisobutyrophenone, 2-Benzoyl-2-bromopropane, Grunwald-Winstein equations
Section
Research Article
Issue
Vol. 9 No. 1 (2018): March 2018
Dates
Received 2018-01-03
Accepted 2018-01-26
Published 2018-03-31
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Dennis Neil Kevill
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA
https://orcid.org/0000-0002-1921-7184
Chang-Bae Kim
Department of Chemistry, Dan-Kook University, Hannam-dong, Yongsan-gu, Seoul 140-714, Korea
Malcolm John D’Souza
Department of Chemistry, Wesley College, 120 North State Street, Dover, Delaware 19901-3875, USA
https://orcid.org/0000-0002-9368-790X

Abstract

A Grunwald-Winstein treatment of the specific rates of solvolysis of α-bromoisobutyro phenone in 100% methanol and in several aqueous ethanol, methanol, acetone, 2,2,2-trifluoroethanol (TFE), and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) mixtures gives a good logarithmic correlation against a linear combination of NT (solvent nucleophilicity) and YBr (solvent ionizing power) values. The l and m sensitivity values are compared to those previously reported for α-bromoacetophenone and to those obtained from parallel treatments of literature specific rate values for the solvolyses of several tertiary mesylates containing a C(=O)R group attached at the α-carbon. Kinetic data obtained earlier by Pasto and Sevenair for the solvolyses of the same substrate in 75% aqueous ethanol (by weight) in the presence of silver perchlorate and perchloric acid are analysed using multiple regression analysis.


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Kevill, D. N.; Kim, C.-B.; D’Souza, M. J. Correlation of the Rates of Solvolysis of α-Bromoisobutyrophenone Using Both Simple and Extended Forms of the Grunwald-Winstein Equation and the Application of Correlation Analysis to Related Studies. Eur. J. Chem. 2018, 9, 1-6.

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Supporting Agencies

The American Chemical Society Petroleum Research Fund (PRF# 38163-AC4), the National Institute of General Medical Sciences (P20GM103446), a National Science Foundation (NSF) EPSCoR grant IIA-1301765.
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