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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Dennis Neil Kevill
Chang-Bae Kim
Malcolm John D’Souza

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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References

[1]. Kevill, D. N.; Kim, C. B. J. Org. Chem. 2005, 70, 1490-1493.
https://doi.org/10.1021/jo048103d

[2]. Grunwald, E.; Winstein, S. J. Am. Chem. Soc. 1948, 70, 846-854.
https://doi.org/10.1021/ja01182a117

[3]. Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951, 73, 2700-2707.
https://doi.org/10.1021/ja01150a078

[4]. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. 2008, 61-66.
https://doi.org/10.3184/030823408X293189

[5]. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121-158.

[6]. Kevill, D. N. in Advances in Quantitative Structure-Property Relationships; Charton, M. Ed.; JAI Press: Greenwich, CT. USA, 1996; Volume 1, pp 81-115.
https://doi.org/10.1016/S1874-527X(96)80006-5

[7]. Pasto, D. J.; Garves, K.; Serve, M. P. J. Org. Chem. 1967, 32, 774-778.
https://doi.org/10.1021/jo01278a057

[8]. Schadt, F. L.; Bentley, T. W.; Schleyer, P. V. R. J. Am. Chem. Soc. 1976, 98, 7667-7675.
https://doi.org/10.1021/ja00440a037

[9]. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845-1850.
https://doi.org/10.1021/jo00005a034

[10]. Creary, X. J. Am. Chem. Soc. 1984, 106, 5568-5577.
https://doi.org/10.1021/ja00331a029

[11]. Creary, X. Acc. Chem. Res. 1985, 18, 3-8.
https://doi.org/10.1021/ar00109a002

[12]. Creary, X. Chem. Rev. 1991, 91, 1842-1878.
https://doi.org/10.1021/cr00008a001

[13]. Begue, J. P.; Charpentier-Morize, M. Acc. Chem. Res. 1980, 13, 207-212.
https://doi.org/10.1021/ar50151a003

[14]. Kevill, D. N. in the Chemistry of the Functional Groups, Supplement D (Eds. Patai, S. and Rappoport, Z.), John Wiley and Sons, New York, 1983, Chapter 20, pp. 933-984.

[15]. Pasto, D. J.; Sevenair, J. P. J. Am. Chem. Soc. 1971, 93, 711-716.
https://doi.org/10.1021/ja00732a026

[16]. Kevill, D. N.; Kolwyck, K. C.; Weitl, F. L. J. Am. Chem. Soc. 1970, 92, 7300-7306.
https://doi.org/10.1021/ja00728a012

[17]. Rappoport, Z.; Kaspi, J. J. Am. Chem. Soc. 1974, 96, 4518-4530.
https://doi.org/10.1021/ja00821a027

[18]. Bentley, T. W.; Bowen, C. T.; Parker, W.; Watt, C. I. F. J. Chem. Soc., Perkin Trans. 2 1980, 1244-1252.
https://doi.org/10.1039/P29800001244

[19]. Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 5741-5747.
https://doi.org/10.1021/ja00385a031

[20]. Kevill, D. N.; Ryu, Z. H. Int. J. Mol. Sci. 2006, 7, 451-455.
https://doi.org/10.3390/i7100451

[21]. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. 1993, 5, 174-175.

[22]. Kevill, D. N.; Anderson, S. W.; Fujimoto, E. K. in Nucleophilicity (Eds. Harris, J. M. and McManus, S. P.), Advances in Chemistry Series, No. 215, American Chemical Society, Washington, DC, 1987, pp. 269-283.

[23]. Bentley, T. W.; Carter, G. E. J. Org. Chem. 1983, 48, 579-584.
https://doi.org/10.1021/jo00152a033

[24]. Hoffmann, H. M. R. J. Chem. Soc. 1965, 6762-6769.
https://doi.org/10.1039/jr9650006762

[25]. Abraham, M. H.; Grellier, P. L.; Abboud, J. L. M.; Doherty, R. M.; Taft, R. W. Can. J. Chem. 1988, 66, 2673-2686.
https://doi.org/10.1139/v88-420

[26]. Bentley, T. W.; Bowen, C. T.; Brown, H. C.; Chloupek, F. J. J. Org. Chem. 1981, 46, 38-42.
https://doi.org/10.1021/jo00314a008

[27]. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd Ed.; Cornell University Press: Ithaca, N.Y., USA, 1969; pp. 454-457.

[28]. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, NY, USA, 1987; pp. 373-375.

[29]. Slutsky, J.; Bingham, R. C.; Schleyer, P. V. R.; Dickason, W. C.; Brown, H. C. J. Am. Chem. Soc. 1974, 96, 1969-1970.
https://doi.org/10.1021/ja00813a071

[30]. Isaacs, N. Physical Organic Chemistry, 2nd ed, Addison Wesley Longman, Harlow, Essex, UK, 1995, pp. 449-450.

[31]. Fry, J. L.; Lancelot, C. J.; Lam, L. K. M.; Harris, J. M.; Bingham, R. C.; Raber, D. J.; Hall, R. E.; Schleyer, P. V. R. J. Am. Chem. Soc. 1970, 92, 2538-2540.
https://doi.org/10.1021/ja00711a053

[32]. Cope, A. C.; Graham, E. S. J. Am. Chem. Soc. 1951, 73, 4702-4706.
https://doi.org/10.1021/ja01154a065

[33]. Kevill, D. N.; Cromwell, N. H. J. Org. Chem. 1964, 29, 499-502.
https://doi.org/10.1021/jo01025a516

[34]. Kevill, D. N.; Park, K. H.; Koh, H. J. J. Phys. Org. Chem. 2011, 24, 378-384.
https://doi.org/10.1002/poc.1767

[35]. Kevill, D. N.; Goken, E. G.; Park, B. C. J. Chem. Res. 2006, 173-175.
https://doi.org/10.3184/030823406776330639

[36]. D'Souza, M. J; Ryu, Z. H.; Park, B. C.; Kevill, D. N. Can. J. Chem. 2008, 86, 359-367.
https://doi.org/10.1139/v08-028

[37]. D'Souza, M. J.; Shuman, K. E.; Omondi, A. O.; Kevill, D. N. Eur. J. Chem. 2011, 2, 130-135.
https://doi.org/10.5155/eurjchem.2.2.130-135.405

[38]. Kyong, J. B.; Lee, Y.; D'Souza, M. J.; Mahon, B. P.; Kevill, D. N. Eur. J. Chem. 2012, 3, 267-272.
https://doi.org/10.5155/eurjchem.3.3.267-272.624

[39]. Kevill, D. N.; Ryu, Z. H.; D'Souza, M. J. Eur. J. Chem. 2017, 8, 162-167.
https://doi.org/10.5155/eurjchem.8.2.162-167.1566

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