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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


Dennis Neil Kevill (1) orcid , Chang-Bae Kim (2) , Malcolm John D’Souza (3,*) orcid

(1) Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA
(2) Department of Chemistry, Dan-Kook University, Hannam-dong, Yongsan-gu, Seoul 140-714, Korea
(3) Department of Chemistry, Wesley College, 120 North State Street, Dover, Delaware 19901-3875, USA
(*) Corresponding Author

Received: 03 Jan 2018 | Revised: 26 Jan 2018 | Accepted: 26 Jan 2018 | Published: 31 Mar 2018 | Issue Date: March 2018

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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Keywords


Solvolysis; Mechanism; Correlation; α-Bromoisobutyrophenone; 2-Benzoyl-2-bromopropane; Grunwald-Winstein equations

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DOI: 10.5155/eurjchem.9.1.1-6.1680

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Funding information


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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How to cite


Kevill, D.; Kim, C.; D’Souza, M. Eur. J. Chem. 2018, 9(1), 1-6. doi:10.5155/eurjchem.9.1.1-6.1680
Kevill, D.; Kim, C.; D’Souza, M. 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), 1-6. doi:10.5155/eurjchem.9.1.1-6.1680
Kevill, D., Kim, C., & D’Souza, M. (2018). 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. European Journal of Chemistry, 9(1), 1-6. doi:10.5155/eurjchem.9.1.1-6.1680
Kevill, Dennis, Chang-Bae Kim, & Malcolm John D’Souza. "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." European Journal of Chemistry [Online], 9.1 (2018): 1-6. Web. 29 May. 2023
Kevill, Dennis, Kim, Chang-Bae, AND D’Souza, Malcolm. "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" European Journal of Chemistry [Online], Volume 9 Number 1 (31 March 2018)

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