Spectroscopic determination of acidity constants of some monoazo resorcinol derivatives

Journal of Chemical and Engineering Data

Volumn 53, Issue 5, 2008, Pages 1049-1055

  Berber, Halil ^a   Ogretir, Cemil ^b   Lekesiz, Emine Cigdem Sev ^a   Ermis, Emel ^a  

^a ANADOLU UNIVERSITY   (Turkey)

^b ESKISEHIR OSMANGAZI UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY CONSTANTS; SPECTROSCOPIC DETERMINATION;

PHENOLS;

EID: 51949105637     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je700488t     Document Type: Article

References (29)

1. Klotz, I. M.; Fiess, H. A.; Ho, J. Y. C.; Mellody, M. The Position of the Proton in Substituted Azobenzene Molecules. J. Am. Chem. Soc. 1954, 76 (20), 5136-5140.
2. Sawicki, E. Physical Properties of the Aminoazobenzene Dyes. IV. The Position of Proton Addition. J. Org. Chem. 1957, 22, 365-367.
3. Rogers, M. T.; Campbell, T. W.; Maatman, R. W. The Ionization Constants of Some p-Substituted p'-Dimethylaminoazobenzenes. J. Am. Chem. Soc. 1951, 73 (11), 5122-5124.
4. Badger, G. M.; Buttery, R. G.; Lewis, G. E. Aromatic Azo-Compounds, Part I. Oxidation of cis- and trans-azobenzene. J. Chem. Soc. 1953, 2143-2147.
5. Jaffé, H. H. Theoretical Considerations Concerning Hammett's Equation. IV. Calculation of ρ-Values. J. Chem. Phys. 1953, 21, 415.
6. Klotz, I. M.; Fiess, H. A.; Ho, J. Y. C.; Mellody, M. The Position of the Proton in Substituted Azobenzene Molecules. J. Am. Chem. Soc. 1954, 76 (20), 5136-5140.
7. Jaffé, H. H.; Gardner, R. W. Tautomeric Equilibria. IV. The Basicities of Monosubstituted Azobenzenes. An Acidity Scale in 20% Ethanolic Aqueous Sulfuric Acid1-3. J. Am. Chem. Soc. 1958, 80 (2), 319-323.
8. Zollinger, H. Color chemistry: Synthesis, properties and applications of organic dyes and pigments, 2nd ed.; VCH: Weinheim, 1991.
9. Hughes, E. D.; Ingold, C. K.; Ridd, J. H. Nitrosation, diazotisation, and deamination. Part I-VI. Principles, background, and method for the kinetic study of diazotisation. J. Chem. Soc 1958,58, 65, 70, 77, 82, 86.
10. Cookson, R. F. The Determination of Acidity Constants. Chem. Rev. 1974, 74 (1), 5-28.
11. Bowden, K. Acidity Functions for Strongly Basic Solutions. Chem. Rev. 1966, 66 (2), 119-131.
12. Perrin, D. D. Buffers for pH and Metal Jon Control; Chapman and Hall: London, U.K., 1971.
13. Albert, A.; Serjeant, E. P. The Determination of Ionisation Constants; Chapman and Hall Ltd.: London U.K., 1971.
14. Wiberg, B. K. Physical Organic Chemistry; Wiley: New York, 1963.
15. Katritzky, A. R. Physical Method of Heterocyclic Chemistry; Academic Press: New York, 1963; p 1.
16. Jorgenson, M. J.; Hartter, D. R. A. Critical Re-evaluation of The Hammett acidity Function at Moderate and High Acid Concentrations of Sulfuric Acid. New Ho Values Based Solely on a Set of Primary Aniline Indicators. J. Am. Chem. Soc. 1963, 85 (7), 878-883.
17. Greig, C. C.; Johnson, C. D. The Protonation of Aromatic Carbonyl Compounds, A. J. Am. Chem. Soc. 1968, 90 (23), 6453-6457.
18. Johnson, C. D.; Katritzky, A. R.; Ridgewell, B. J.; Shakir, N.; White, A. M. Applicability of Hammett Acidity Functions to Substituted Pyridines and Pyridine 1-oxides. Tetrahedron 1965, 21, 1055-1065.
19. Deno, N. C.; Jaruzelski, J. J. Carbonium Ions. I. An Acidity Function (Co) Derived From Arylcarbonium Ion Equilibriums. J. Am. Chem. Soc. 1955, 77, 3044-3051.
20. Orloft, M. K.; Fitts, D. D. Semiempirical S.C.F.-L.C.A.O.-M.O. Treatment of Futan. J. Chem. Phys. 1963, 38, 2334-2338.
21. (a) Lowry, T. L.; Richardson K. S. The Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper&Row: N.Y., 1981; p 239.
22. (b) Cox, R. A.; Yates, K. Can. J. Chem. 1980, 59, 1560.
23. (c) Bagno, A.; Scorrano, G. Gazzeta Chim. Ital. 1987, 117, 475.
24. (d) Cox, R. A. Adv. Phys. Org. Chem. 2000, 35, 1-66.
25. Schawarzenbach, G.; Sulzberger, R. The Alkalinity of Strong Solutions of the Alkali Hydroxides. Helv. Chim. Acta 1944, 27, 348-362.
26. Yates, K.; McClelland, R. A. Mechanisms of Ester Hydrolysis in Aqueous Sulfuric Acids. J. Am. Chem. Soc. 1967, 89, 2686-2692.
27. Wang, W.; Gong, S.; Chen, Y.; Meng, I. The Effects of Intramolecular Hydrogen Bonding on the Reaction of Phenols with Epoxide in the Presence of Nano Calcium Carbonate. Supramol. Chem. 2006, 18 (4), 311-315.
28. Graham Solomons, T. W.; Fryhle C. B. Organic chemistry, 7th ed.; J. Wiley: New York, 2000; p 1023.
29. Johnson, C. D. The Hammett Equation; Cambridge University Press: New York, 1973.