Correlation of solvolysis rates 50 years later

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6512-6514

  Catalán, Javier ^a   Díaz, Cristina ^a   García Blanco, Francisco ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; SOLVENT; TERT BUTYLCHLORIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CORRELATION FUNCTION; DENATURATION; ELECTRON TRANSPORT; IONIZATION; PARAMETER; PROTEIN FOLDING; REACTION TIME; SOLUBILITY; SOLVATION;

EID: 18144440887     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990588w     Document Type: Article

References (43)

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27. 27 by themselves, they will lead to a cavity term that is small or nonexistent.
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29. This fit excludes aromatic solvents to avoid the need to include the polarizability term, δ, and also the gas phase for lack of parameter values.
30. This conclusion should be taken cautiously as the basicity scale of Swain et al. is known to describe not solvent basicity but rather solvent polarity-polarizability (see Figures 9 and 10 in ref 30).
31. Catalán, J.; Díaz, C.; López, V.; Pérez, P.; de Paz, J.-L. G.; Rodríguez, J. G. Liebigs Ann. 1996, 1785.
32. Catalán, J.; López, V.; Pérez, P.; Martín-Villamil, R.; Rodríguez, J.-G. Liebigs Ann. 1995, 241.
33. Catalán, J.; López V.; Pérez, P. Liebigs Ann. 1995, 793.
34. Catalán, J.; Díaz, C. Liebigs Ann./Recueil 1997, 1941.
35. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1977, 98, 377.
36. Catalán, J.; Díaz, C. Eur. J. Org. Chem. 1999, 885.
37. The experimental data values for log k corresponding to solvents (water, methanol, ethanol, n-butanol, n-hexanol, n-octanol, 2-propanol, 2-methyl-2-propanol, ethylene glycol, glycerol, 2,2,2-trifluoroethanol, formamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, acetonitrile, acetone, acetic acid, ethyl acetate, 1,4-dioxane, tetrahydrofuran, benzene, chlorobenzene, nitrobenzene, nitromethane, diethyl ether, n-heptane) and the gas phase were compiled from the following: (a) References 22 and 23 and references therein. (b) Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions; Palm, V. A., Ed.; Moscow, 1977; Tom. II, Vol. II.
38. The experimental data values for log k corresponding to solvents (water, methanol, ethanol, n-butanol, n-hexanol, n-octanol, 2-propanol, 2-methyl-2-propanol, ethylene glycol, glycerol, 2,2,2-trifluoroethanol, formamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, acetonitrile, acetone, acetic acid, ethyl acetate, 1,4- dioxane, tetrahydrofuran, benzene, chlorobenzene, nitrobenzene, nitromethane, diethyl ether, n-heptane) and the gas phase were compiled from the following: (a) References 22 and 23 and references therein. (b) Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions; Palm, V. A., Ed.; Moscow, 1977; Tom. II, Vol. II.
39. The experimental data values for log k corresponding to 120 solvent mixtures were gathered in the following references: (a) Reference 3. (b) Reference 36b. (c) Shiner, V. J., Jr.; Dowd, W.; Fisher, R. D.; Hartshorn, S. R.; Kessick, M. A.; Milakofsky, L.; Rapp, M. W. J. Am. Chem. Soc. 1969, 91, 4838.
40. The experimental data values for log k corresponding to 120 solvent mixtures were gathered in the following references: (a) Reference 3. (b) Reference 36b. (c) Shiner, V. J., Jr.; Dowd, W.; Fisher, R. D.; Hartshorn, S. R.; Kessick, M. A.; Milakofsky, L.; Rapp, M. W. J. Am. Chem. Soc. 1969, 91, 4838.
41. The experimental data values for log k corresponding to 120 solvent mixtures were gathered in the following references: (a) Reference 3. (b) Reference 36b. (c) Shiner, V. J., Jr.; Dowd, W.; Fisher, R. D.; Hartshorn, S. R.; Kessick, M. A.; Milakofsky, L.; Rapp, M. W. J. Am. Chem. Soc. 1969, 91, 4838.
42. This equation has been determined using the program MINIT-AB. Inc. State College PA (USA) v. 9.
43. Catalán, J.; Díaz, C.; García-Blanco, F. Work in progress.