Journals / Gazi University Journal of Science / 2026 / Volume: 27 Issue: 2

Spectrophotometric determination of the acidity dissociation constants of symmetric Schiff base derivatives

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2014-06-27
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Objective & Hypothesis:800x600 In this study, the acidity constants of series symmetric Schiff base derivatives have been determined using the UV-visible spectrophotometric method at a temperature of 25(±0.1) °C.
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Key Findings & Data:The first and the second protonated acidity constants ( p K a1 and p K a2 ) have been found to cause the protonation of the imine nitrogen atom for all molecules.
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📍Scope:Comprehensive Sample
⚙️Variables:Spectrophotometric determination · Symmetric Schiff base · Acidity Dissociation Constants

Abstract

800x600 In this study, the acidity constants of series symmetric Schiff base derivatives have been determined using the UV-visible spectrophotometric method at a temperature of 25(±0.1) °C. The deprotonated acidity constants ( p K a ) have been found to be associated with the deprotonation of phenolate oxygen. The first and the second protonated acidity constants ( p K a1 and p K a2 ) have been found to cause the protonation of the imine nitrogen atom for all molecules. The deprotonated acidity constants ( p K a ) were found for molecules 5 ( 9.088), 8 ( 9.848), 6 ( 10.243), 2 ( 10.2569), 3 (10.297), 1 (10.587), 7 ( 10.692) and 4 (10.804). The first protonation ( pK a1 ) was found for molecules 2 ( 3.432), 5 ( 4.207), 8 ( 4.612), 7 ( 4.758), 4 (4.995), 1 (5.288), 6 ( 5.606) and 3 (6.452). The second protonation ( pK a2 ) was found for molecules 2 ( -5.384), 8 ( -5.165), 5 ( -5.028), 7 ( -4.775), 4 (-4.518), 1 (-4.111), 6 ( -3.866) and 3 (-3.212). Normal 0 21 false false false TR X-NONE X-NONE MicrosoftInternetExplorer4

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Cite This Article

Türkoğlu, G., Berber, H., Özkütük, M. (2014). Spectrophotometric determination of the acidity dissociation constants of symmetric Schiff base derivatives. Gazi University Journal of Science, Volume: 27 Issue: 2. https://ajindex.com/articles/1269674

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References (60)

  1. Calligaris, M., Randaccio, L., In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: London,Vol. 2, p 715, (1987).
  2. Jia, H.P., Li, W., Ju, Z.F., Zhang, J., “Synthesis, Structure, and Magnetic Properties of a Novel Mixed-Bridged Heterometal Tetranuclear Complex [Mn2Ni2(MeOSalen)2(l1,1-N3)2(N3)2]”,
  3. Chem. Commun., 10: 397-400 (2007).
  4. Inorg. [3] Cohen, M.D., Schmidt, G.M.J., Flavian, S., “Topochemistry. VI. Experiments on Photochromy and Thermochromy of Crystalline Anils of Salicylaldehydes”, J. Chem. Soc., 2041-2051 (1964).
  5. Lahav, M., Schmidt, G.M.J., “Tophochemistry. XXIII. The Solidstate Photochemistry at 25 Deg of Some Muconic Acid Derivatives”, J. Chem. Soc. B, 312-317, (1967).
  6. Hadjoudis, E., Vitterakis, M., Moustakali-Mavridis, I., “Photochromism and Thermochromism of Schiff Bases in the Solid and in Rigid Glasses”, Tetrahedron, 43: 1345-1360 (1987).
  7. Kaya, I., Yıldırım, M., Avcı, A., “Synthesis and Characterization of Fluorescent Polyphenol Species Derived From Methyl Substituted Aminopyridine Based Schiff Bases: The Effect of Substituent Position on Optical, Electrical, Electrochemical, and Fluorescence Properties”, Synth. Met., 160: 911-920 (2010).
  8. Ramakrishna, D., Bhat, B.R., Karvembu, R., “Catalytic Oxidation of Alcohols by Nickel (II) Schiff
  9. Triphenylphosphine in Ionic Liquid: an Attempt towards Oxidation
  10. Commun., 11: 498-501 (2010).
  11. Containing Process”,
  12. Catal. [8] Soltani, N., Behpour, M., Ghoreish
  13. i, S. M., Naeimi H., “Corrosion Inhibition of Mild Steel in Hydrochloric Acid Solution by Some Double Schiff Bases”, Corr. Sci., 52: 1351-1361 (2010).
  14. Sabaa, M.W., Mohamed, R.R., Oraby, E.H., “Vanillin–Schiff’s Bases as Organic Thermal Stabilizers and Co-stabilizers for Rigid Poly(vinyl chloride)”, Europ. Poly. J., 45: 3072-3080 (2009). [10]
  15. Chakraborty, A., Kumar, P., Ghosh, K., Roy, P., “Evaluation of a Schiff Base Copper Complex Compound as Potent Anticancer Molecule with Multiple Targets of Action”, Europ. J. Pharm., 647: 1-12 (2010).
  16. Kamel, M. M., Ali, H. I., Anwar, M.M., Mohamed, N.A. Soliman, A.M., “Synthesis, Antitumor Activity and
  17. Sulfonamide-Schiff's Benzothiazinones
  18. Derivatives”, Europ. J. Medic. Chem., 45: 572-580 (2010). Study of Novel Bases,
  19. Thiazolidinones, and Their c-nucleoside [12]
  20. Roswadowski, Z., Majewski, E., Dziembowska, T., Hansen, P.E., “Deuterium Isotope Effects On 13C Chemical
  21. Hydrogenbonded Schiffs Bases”, J. Chem. Soc. Perkin Trans., 2: 2809 (1999).
  22. Intramolecularly Zgierski,
  23. Photochromism of N-salycylidene-R-benzylamine”, J. Chem. Phys., 115: 8351 (2001). Study of [14]
  24. Filarowski, A., Koll, A., Glowiak, T.,Majewski, E., Dziembowska, T., “Proton-transfer Reaction in N- methyl-2-hydroxy Schiff Bases”, Ber. Bunsen-Ges. Phys. Chem., 97: 393 (1993). [15] Koll, Dziembowska,
  25. Conformation of Schiff Bases with Intramolecular Hydrogen Bonds”, J. Mol. Struct., 552: 193-204 (2000). Jagodzinska, Moments and [16]
  26. Gilli, P., Ferretti, V., Bertolasi, V., Gilli, G., A Novel Approach to Hydrogen Bonding Theory In Advances in Molecular Structure Research, Hargittai, M., Hargittai, I., Eds.; JAI Press: Greenwich, CT, Vol. 2, p 667 (1996). [17]
  27. Theoretical Investigation”, J. Pharm. Biomed. Anal., 15: 1667–1678 (1997). and [19]
  28. Frey, P.A., Kokesh. F.O., Wcstheimer, F.H., “A Reporter Group at the Active Site of Acetoacetate Decarboxylase
  29. Nitrophenol”, J. Am. Chem. Soc., 93: 7266-7270 (1971). Constant of the [20]
  30. Türkoğlu, G., Berber H., Dal, H., Öğretir, C., “Synthesis,
  31. theoretical study of some new Schiff base derivatives”, Spectroc. Acta Part A., 79, 1573– 1583 (2011). tautomerism and [21]
  32. Türkoğlu, G., Bazı Difenolik Schiff Bazlarının Sentezi ve Yapılarının Aydınlatılması, Anadolu Üniversitesi, Yüksek Lisans Tezi, Kimya Anabilim Dalı, Eskişehir, (2007). [22]
  33. Albert, A., Serjeant, E.P., The Determination of Ionisation Constants, Chapman and Hall London, U.K., (1971). [23]
  34. Wiberg, B.K., Physical Organic Chemistry, Wiley: New York, (1963). [24]
  35. Hammett, L.P., Deyrup, A.J., “A Series of Simple Basic Indicators. I. The Acidity Functions of Mixtures of Sulfuric and Perchloric Acids With Water”, J. Am. Chem. Soc., 54(7): 2721-2739 (1932). [25]
  36. Jorgenson, M.J., Hartter, D.R., “A Critical Re- evaluation of the Hammett Acidity Function at Moderate and High Acid Concentrations of Sulfuricacid New Ho Values Based Solely on a Set of Primary Aniline Indicators”, J. Am. Chem. Soc., 85: 878-883 (1963). [26]
  37. Johnson, C.D., Katritzky, A.R., Shapiro, S., “The protonation of Aromatic Carbonyl Compounds”, J. Am. Chem. Soc., 9: 6453-6457 (1968). [27]
  38. Cookson, R.F., “The Determination of Acidity Constants”, Chem. Rev., 74: 1 (1974). [28]
  39. Bowden, K., “Acidity Functions for Strongly Basic Solutions”, Chem. Rev., 66: 2 (1966). [29]
  40. Perrin, D.D., Buffers for pH and Metal Ion Control; Chapman and Hall: London, U.K., (1971). [30]
  41. Deno, N.C., Jaruzelski, J.J. “Carbonium ions. I. An acidity Function (Co) Derived from Arylcarbonium Ion Equilibriums”, J. Am. Chem. Soc., 77: 3044- 3051 (1955). [31]
  42. Orloft, M.K., Fitts, D.D., “Semiempirical S.C.F.- L.C.A.O.-M.O. Treatment of Furan”, J. Chem. Phys., 38: 2334-2338 (1963). [32]
  43. Yates, K., Stevens, J.B., Katritzky, A.R., “The Iionization Behavior of Amides in Concentrated Sulfuric Acids. I. A New Acidity Function Based on a Set of Primary Amide Indicators”, Can. J. Chem., 42: 1957-1970 (1964). [33]
  44. Arnett, E.M., Mach, G.W., “Solvent Effects in Organic Chemistry. IV. The Failure of Tertiary Aromatic Amines as Hammett Bases“, J. Am. Chem. Soc., 86: 2671-2677 (1964). [34]
  45. Yates, K., McClelland, R.A., “Mechanisms of ester hydrolysis in aqueous sulfuric acids “, J. Am. Chem. Soc., 89(11): 2686-2692 (1967). [35]
  46. Schawarzenbach, G., Sulzberger, R., “The Alkalinity of Strong Solutionsof the Alkali Hydroxides”, Helv. Chim. Acta, 27: 348-362 (1944). [36]
  47. Rochester, C.H., Acidity Functions, Academic Press: London, (1970).
  48. Jones, J.R., The Ionization of Carbon Acids, Academic Press: New York, (1973). [38]
  49. Özkütük, M., Öğretir, C., Arslan, T., Kandemirli, F., Köksoy, B., “An Experimental Study On Acid Dissociation Constants of Some Novel İsatin Thiosemicarbazone Derivatives”, J. Chem. Eng. Data, 55: 2714–2718 (2010). [39]
  50. Öğretir, C., Berber, H., Asutay, O., “Spectroscopic Determination of Acid Dissociation Constants of Some Imidazole Derivatives”, J. Chem. Eng. Data, 46: 1540–1543 (2001).
  51. Öğretir, C., Dal, H.; Berber, H., Taktak, F.F., “Spectroscopic Determination of Acid Dissociation Constants of Some Pyridyl Shiff Bases”, J. Chem. Eng. Data, 51: 46–50 (2006). [41]
  52. Berber, H., Öğretir, C., Sev Lekesiz, E.Ç., Ermis, E., “Spectroscopic Determination of Acidity Constants of Some Monoazo Resorcinol Derivatives”, J. Chem. Eng. Data, 53: 1049–1055 (2008). [42]
  53. Gülseven Sıdır, Y., Sıdır, İ., Berber H., Taşal, E., Öğretir, C., “Spectroscopic Determination of Acid Dissociation Constants of Some Novel Drug Precursor 6-Acylbenzothiazolon Derivatives”, J. Chem. Eng. Data, 55: 4752–4756 (2010). [43]
  54. Taktak, F.F., Berber, H., Dal, H., Öğretir, C., “Spectroscopic
  55. Dissociation Constants of Some 2-Hydroxy Schiff Base Derivatives”, J. Chem. Eng. Data, 56: 2084– 2089 (2011). of the Acid [44] Gülseven
  56. “Spectroscopic Determination of Acid Dissociation Constants of N-Substituted-6-acylbenzothiazolone Derivatives”, J. Phys. Chem. A, 115: 5112–5117 Öğretir, C., Görgün, K., Özkütük, M., Sakarya, H.C., “Determination and evaluation of acid dissociation constants of some novel benzothiazole Schiff bases and their reduced analogs by spectroscopy”, ARKIVOC, vii: 197-209 (2009). [46] Öğretir,
  57. “Spectroscopic Determination of Acid Dissociation Constants of Some Biologically Active 6-Phenyl- 4,5-dihydro-3(2H)-pyridazinone Derivatives”, J. Chem. Eng. Data, 47: 1396–1400 (2002). Ş., [47]
  58. Hansch, C., Leo, A., Taft, R.W., “A Survey of Hammett Substituent Constants and Resonance and Field Parameters”, Chem. Rev., 97: 165-195 (199l). [48]
  59. Ang, K., Tan, S., “Ionization Constants of Some Hydroxy-Pyrones at 25°C”, J. Chem. Soc. Perkin Trans., 2: 1525-1526 (1979).
  60. Dean, J.A., Edited by, Lange's Handbook of Chemistry, (15th Edition); McGraw-Hill Mar Vol: 2, (2001).