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For recent work and leading references, see: 1980, 16, 2089-2092; 1981, 17, 260-265; During the past 12 years A. I. Shatenshtein and his co-workers have developed an acidity scale in Me2SO and an ion-pair acidity scale in DME, using Li+, K+, and Cs+counterions
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During the past 12 years A. I. Shatenshtein and his co-workers have developed an acidity scale in Me2SO and an ion-pair acidity scale in DME, using Li+, K+, and Cs+counterions. (The pKa's measured in Me2SO, when placed on an absolute scale, usually agree with ours to within ±0.3 pK unit.) For recent work and leading references, see: Shatenshtein, A. I., et al. J. Org. Chem. USSR (Engl. Transl.) 1978, 14, 829-833; 1980, 16, 2089-2092; 1981, 17, 260-265; 1982, 18, 6-10; 1983, 19, 405–408. (b) Bors, D. A.; Kaufman, M. J.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1985, 107, 6975–6982. (c) Fraser, R. R.; Mansour, T. S.; Savard, S. J. Org. Chem. 1985, 50, 3232–3234. (d) Lagowski, J. J. Pure Appl.Chem. 1971. 25. 429–456.
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Bartmess, J. E.; McLver, R. T., Jr. Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic: New York, 1979; Vol. 2, Chapter 11. An update of this acidity scale will soon be published by J. E. Bartmess in The Journal of Physical and Chemical Reference Data.
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Bartmess in The Journal of Physical and Chemical Reference Data.
, vol.2
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Bartmess, J.E.1
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See ref 11 and Kaufman et al. for additional examples and discussion.
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Bordwell, F. G.; Drucker, G. F.; Andersen, N. H.; Denniston, A. D. J. Am. Chem. Soc. 1986, 108, 7310–7313. See ref 11 and Kaufman et al. (Kaufman, M. J.; Gronert, S.; Burs, D. A.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1987, 109, 602–603) for additional examples and discussion.
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(b)Algrim, D. J. Org. Chem. 1976, 41, 2507–2508.
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Bordwell, F. G.; Van Der Puy, M.; Vanier, N. R. J. Org. Chem. 1976, 41, 1884-1885. (b) Bordwell, F. G.; Algrim, D. J. Org. Chem. 1976, 41, 2507–2508.
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(b)Cheng, J. P.; Marchot, E. J. Macromol. Chem., Macromol. Symp. 1988, 13/14, 21–31.
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For a review, see: Eds.; Advances in Chemistry 215; American Chemical Society: Washington, DC
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For a review, see: Bordwell, F. G.; Hughes, D. L.; Cripe, T. A. in Nucleophilicity; Harris, M. J., McManus, S. P., Eds.; Advances in Chemistry 215; American Chemical Society: Washington, DC, 1987; Chapter 9.
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The thermodynamic cycle on which this method was based was derived by Nicholas and Arnold. 49
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Bordwell, F. G.; Bausch, M. J. J. Am. Chem. Soc. 1986, 108, 2473–2474. The thermodynamic cycle on which this method was based was derived by Nicholas and Arnold.49
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Over large ranges of ΔG° the Marcus equation
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