Ruthenium(III)-Catalyzed Oxidation of Vanillin by Anticancer Hexachloroplatinate(IV) Complex in Perchloric Acid Solutions: A Kinetic Study
American Journal of Physical Chemistry
Volume 5, Issue 3, June 2016, Pages: 56-64
Received: Apr. 3, 2016; Accepted: Apr. 9, 2016; Published: May 3, 2016
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Authors
Ahmed Fawzy, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia; Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt
Ishaq A. Zaafarany, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia
Khalid S. Khairou, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia
Layla S. Almazroai, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia
Badriah A. Al-Jahdali, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia
Tahani M. Bawazeer, Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia
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Abstract
The kinetics of oxidation of vanillin (VAN) by hexachloroplatinate(IV) has been investigated in perchloric acid solutions in the presence of ruthenium(III) catalyst at a constant ionic strength of 1.0 mol dm-3 and at 25°C. The progress of the reaction was followed spectrophotometrically. The reaction was not proceeding in the absence of the catalyst. The reaction exhibited first order kinetics with respect to both [HCP] and [Ru(III)] and less than unit order with respect to both [VAN] and [H+]. Increasing ionic strength and dielectric constant were found to increase the oxidation rate. The reaction mechanism adequately describing the kinetic results has been proposed. Both spectral and kinetic evidences revealed formation of an intermediate complex between vanillin substrate and ruthenium(III) catalyst prior to the rate-determining step. The complex reacts with the oxidant (HCP) by an inner-sphere mechanism leading to decomposition of the complex in the rate-determining step to give rise to the final oxidation products which were identified by both spectral and chemical analyses as vanillic acid and tetrachloroplatinate(II). The rate law expression for the catalyzed reaction was deduced. The reaction constants involved in the different steps of the reaction mechanism have been evaluated. The activation parameters associated with the rate-limiting step of the reaction, along with the thermodynamic quantities of the equilibrium constant have been evaluated and discussed.
Keywords
Catalyzed-Oxidation, Vanillin, Hexachloroplatinate(IV), Ruthenium(III), Kinetics, Mechanism
To cite this article
Ahmed Fawzy, Ishaq A. Zaafarany, Khalid S. Khairou, Layla S. Almazroai, Badriah A. Al-Jahdali, Tahani M. Bawazeer, Ruthenium(III)-Catalyzed Oxidation of Vanillin by Anticancer Hexachloroplatinate(IV) Complex in Perchloric Acid Solutions: A Kinetic Study, American Journal of Physical Chemistry. Vol. 5, No. 3, 2016, pp. 56-64. doi: 10.11648/j.ajpc.20160503.12
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Copyright © 2016 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
References
[1]
Liu Y, Liu H, Li Y (2008) Comparative study of the electro-catalytic oxidation and mechanism of nitrophenols at Bi-doped lead dioxide. Appl. Catal. B: Env. 84: 297-302.
[2]
Timy PJ, Nandibewoor ST, Tuwar SM (2006) Kinetics and mechanism of the oxidation of vanillin by hexacyanoferrate (III) in aqueous alkaline medium. J. Solution Chem. 35: 51–62.
[3]
Deepak SM, Chimatadar SA, Nandibewoor ST (2007) Oxidation of vanillin by a new oxidant diperiodatoargentate (III) in aqueous alkaline medium. Ind. Eng. Chem. Res. 46: 1459–1464.
[4]
Mishra P (2009) Kinetics and mechanisms of oxidation of 4-hydroxy-3-methoxy benzaldehyde (vanillin) by Bi(V) in aqueous alkaline medium. Int. J. Pharm. Tech. Res. 1: 1234–1240.
[5]
Kathari C, Pol P, Nandibewoor ST (2002) The kinetics and mechanism of oxidation of vanillin by diperiodatonickelate (IV) in aqueous alkaline medium. Turk. J. Chem. 26: 229–236.
[6]
Patil DG, Magdum PA, Nandibewoor ST (2015) Mechanistic investigations of uncatalyzed and ruthenium(III) catalyzed oxidation of vanillin by periodate in aqueous alkaline medium, J. Solution Chem.44: 1205-1223.
[7]
Satapathy PK, Baral DK, Aswar, AS, Mohanty P (2013) Kinetics and mechanism of oxidation of vanillin by cerium(IV) in aqueous perchlorate medium. Indian J. Chem. Tech. 20: 271–275.
[8]
Keage MC, Kelland MJ, Neidles LR, Warning MJ, ed. (1993) Molecular Aspects of Anticancer Drug DNA Interactions, vol. 1, CRC Press, New York, NY, USA.
[9]
Lemma K, Sargeson A, Elding LI (2000) Kinetics and mechanism for reduction of oral anticancer platinum(IV) dicarboxylate compounds by L-ascorbate ions. J. Chem. Soc. Dalton Trans. 7: 1167-1172.
[10]
Weiss RP, Christian MC (1993) New cisplatin analogues in development. A review. Drugs 46: 360-377.
[11]
Lemma K, Shi T, Elding LI (2000) Kinetics and mechanism for reduction of the anticancer prodrug trans, trans, trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by thiols, Inorg. Chem. 39: 1728–1734.
[12]
Beattie K, Basolo F (1967) Reduction of some platinum(IV) complexes with tris(bipyridine) chromium(II) ion.Inorg. Chem. 6: 2069-2073.
[13]
Beattie K, Basolo F (1971) Two-electron inner-sphere reduction of chloropentaammine-platinum(IV) ion by aquochromium(II) ion. Inorg. Chem. 10: 486-491.
[14]
Moodley KG, Nicol MJ (1977) Kinetics of the reduction of platinum(IV) by tin(II) and copper(I) in aqueous chloride solutions. J. Chem. Soc., Dalton Trans. 239-243.
[15]
Sen Gupta KK, Das S, Sen Gupta S (1988)Kinetics and mechanism of the oxidation of thiosulphate by hexachloroplatinate(IV). Transition Met. Chem. 13: 155-159.
[16]
Hassan RM, Kojima T, Fukutomi T (1982) Kinetics of the oxidation of uranium(IV) by hexachloroplatinate(IV) in aqueous solution. VI International symposium on solute-solute-solvent interactions. Japan, pp. 113.
[17]
Sen Gupta KK, Begum BA, Ghosh SP (1998) Reactivities of osmium(VIII), iridium(IV) and platinum(IV) towards glycolaldehyde. Transition Met. Chem. 23: 295-299.
[18]
Pal B, Sen Gupta KK (2000) Kinetics and mechanism of hexachloroplatinate(IV) reduction by some neutralized alpha-hydroxy acids in a carbonate-hydrogencarbonate buffer medium. Bull. Chem. Soc. Jpn. 73: 553-560.
[19]
Pal B, Sen Gupta KK, Sen PK (2005) Oxidative cleavage of α, β-unsaturated compounds by pentachlorohydroxoplatinate(IV) in alkaline medium. Transition Met. Chem. 30: 593-600.
[20]
Sen Gupta KK, Sen PK, Sen Gupta S (1977) Kinetics of oxidation of hydrazinium ion by platinum(IV).Inorg. Chem. 16: 1396-1399.
[21]
Sen Gupta KK, Sen PK (1977) Kinetics of the oxidation of hydroxylamine by platinum(IV). J. Inorg. Nucl. Chem. 39: 1651-1653.
[22]
Fawzy A (2015) Palladium(II)-catalyzed oxidation of L-tryptophan by hexacyanoferrate(III) in perchloric acid medium: a kinetic and mechanistic approach. J. Chem. Sci.In press.
[23]
Fawzy A (2014) Influence of copper(II) catalyst on the oxidation of L-histidine by platinum(IV) in alkaline medium: a kinetic and mechanistic study. Transition Met. Chem. 39: 567-576.
[24]
Fawzy A (2015) Kinetics and mechanistic approach to the oxidative behavior of biological anticancer platinum(IV) complex towards L-asparagine in acid medium and the effect of copper(II) catalyst. Int. J. Chem. Kinet. 47: 1-12.
[25]
Fawzy A, Asghar BH (2015) Kinetics and mechanism of uncatalyzed and silver(I)-catalyzed oxidation of L-histidine by hexachloroplatinate(IV) in acid medium, Transition Met. Chem. 40: 287-295.
[26]
Asghar BH, Altass HM, Fawzy A (2015) Transition metal ions-catalyzed oxidation of L-asparagine by platinum(IV) in acid medium: akinetic and mechanistic study. Transition Met. Chem., 40: 587–594.
[27]
Fawzy A, Zaafarany IA (2015) Kinetic and Mechanistic Investigation on the Zirconium(IV)-Catalyzed Oxidation of L-Histidine by Hexachloroplatinate(IV) in Acid Medium. Chem. Sci. Rev. Lett., 4: 608-618.
[28]
Fawzy A, Zaafarany IA (2015) Mechanistic investigation of copper(II)-catalyzed oxidation of L-asparagine by hexachloroplatinate(IV) in aqueous alkaline medium: a kinetic approach.J. Multidisc. Eng. Sci. Technol. 2: 1038-1045.
[29]
Asghar BH, Altass HM, Fawzy A (2016) Silver(I)-catalysis of oxidative deamination and decarboxylation of L-asparagine and L-histidine by platinum(IV) in perchloric acid solutions: acomparative kinetics study. J. Env. Chem. Eng. 4: 617-623.
[30]
Choi S, Filotto C, Bisanzo M, Delaney S, Lagasee D, Whitworth JL, Jusko A, Li C, Wood NA, Willingham J, Schwenker A, Spaulding K (1988) Reduction and anticancer activity of platinum(IV) complexes. Inorg. Chem. 37: 2500-2504.
[31]
Fawzy A, Ashour SS, Musleh MA (2014) Base-catalyzed oxidation of L-asparagine by alkaline permanganate and the effect of alkali-metal ion catalysts: Kinetics and mechanistic approach. React. Kinet.Mech. Catal. 111: 443-460.
[32]
Shukla R, Upadhyay SK (2008) Non-ionic micellar inhibition on the rate of oxidation of L-histidine by alkaline hexacyanoferrate(III). Indian J. Chem. 47A: 551-555.
[33]
Georgieva M, Andonovski B (2003) Determination of platinum(IV) by UV spectrophotometry, Anal. Bioanal. Chem. 375: 836-839.
[34]
Vogel AI (1973) Text book of practical organic chemistry, 3rd ed., ELBS Longman, London, 1973, p. 332 and 679.
[35]
Feigl F (1957) Spot Tests in Organic Analysis, Elsevier, New York, NY, USA.
[36]
Fawzy A, Altass HM (2016) Ruthenium(III)-catalyzed oxidation of alginate and pectate biopolymers by chromic acid in aqueous perchlorate solutions: A comparative kinetic study. Transition Met. Chem. 41: 115-124.
[37]
Griffith WP (1967) The chemistry of rare patinum metals, Interscience Publishers pp. 141.
[38]
Kramer J, Koch KR (2006) 195Pt NMR Study of the speciation and preferential extraction of Pt(IV)−mixed halide complexes by diethylenetriamine-modified silica-based anion exchangers, Inorg. Chem. 45: 7843-7855.
[39]
Mason WR (1972) Platinum(II)-catalyzed substitutions of platinum(IV) complexes. Coord. Chem. Rev.7: 241-255.
[40]
Hassan RM, Kojima T, Fukutomi T (1982) Kinetics of the oxidation of uranium(IV) by hexachloroplatinate(IV) in aqueous solution. VI International symposium on solute-solute-solvent interactions. Japan, pp. 113.
[41]
Amis ES (1966) Solvent Effect on Reaction Rates and Mechanism, Academic Press, New York, pp. 28.
[42]
Frost AA, Person RG (1970) Kinetics and mechanism, Wiley Eastern, New Delhi, pp. 147.
[43]
Rochester CH (1971) Progress in Reaction Kinetics. Pergamon Press, Oxford, 1971, pp. 145.
[44]
Laidler K (1965) Chemical Kinetics. McGraw-Hill, New York.
[45]
Michaelis L, Menten ML (1913) The kinetics of invertase action. Biochem Z 49: 333–369.
[46]
Hicks KW, Toppen DL, Linck RG (1972) Inner-sphere electron-transfer reactions of vanadium(II) with azidoamine complexes of cobalt(III). InorgChem11: 310-315.
[47]
Weissberger A (1974) In Investigation of Rates and Mechanism of Reactions in Techniques of Chemistry, John Wiley & Sons, pp. 421.
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