Mechanistic investigation of the oxidation of Cefuroxime by hexacyanoferrate(III) in alkaline conditions

Aftab Aslam Parwaz Khan; Abdullah M. Asiri; Anish Khan; Naved Azum; Malik Abdul Rub; Mohammed M. Rahman; Sher Bahadar Khan; K.S. Siddiqi; Khalid A. Alamry

Journal of Industrial and Engineering Chemistry, Vol.19, No.2, 595-600, March, 2013

DOI10.1016/j.jiec.2012.09.025 Export Citation

Mechanistic investigation of the oxidation of Cefuroxime by hexacyanoferrate(III) in alkaline conditions

Aftab Aslam Parwaz Khan^{1, 2, †}, Abdullah M. Asiri^{1, 2}, Anish Khan^{1, 2}, Naved Azum^{1, 2}, Malik Abdul Rub^{1, 2}, Mohammed M. Rahman^{1, 2}, Sher Bahadar Khan^{1, 2}, K.S. Siddiqi³, and Khalid A. Alamry¹

¹Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
²Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
³Department of Chemistry, Aligarh Muslim University, Aligarh, India

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The reactions of Cefuroxime (CFA) by hexacyanoferrate (III) (HCF(III)) in alkaline medium at a constant ionic strength has been studied spectrophotometrically. It is a first order reaction, but fractional order in both CFA and alkali. Decrease in dielectric constant of the medium decreases the rate of reaction. The effect of added products and ionic strength has also been investigated. A mechanism involving free radicals is proposed. In a composite equilibrium step, CFA binds to HCF(III) to form a complex that subsequently decomposes to the products. The main two products were separated and identified by column chromatography, TLC and FT-IR. There is good agreement between the observed and calculated rate constants under different experimental conditions. The reaction was studied at different temperatures and activation parameters were computed with respect to the slow step of the proposed mechanism.

Keywords:Kinetics;Mechanism;Cefuroxime;Oxidation;HCF(III)

[References]

Brunton LL, Lazo JS, Parker KL, Goodman, Gilman, Thepharmacological Basis of therapeutics, 11th ed., McGraw-Hill, New York (2006)
Jelinska A, Zajac M, Jakubowska M, Reaction Kinetics and Catalysis Letters., 73, 331 (2001)
Dollery C, Therapeutic Drugs Second, 2nd ed., Churchill Livingstone, London UK. C135 (1999)
Okamoto MP, Nakahiro RK, Chin A, Bedikian A, Gill MA, American Journal of Hospital Pharmacy., 51, 463 (1994)
Murillo JA, Lemus JM, Garcia LF, Journal of Pharmaceutical and Biomedical Analysis., 12, 875 (1994)
Bano S, Mohd A, Khan AAP, Siddiqi KS, Journal of Diabetes Science and Technology., 7, 1023 (2011)
Salem H, Askal H, Journal of Pharmaceutical and Biomedical Analysis., 29, 347 (2002)
Ayad MM, Shalaby AA, Abdellatef HE, Elsaid HM, Journal of Pharmaceutical and Biomedical Analysis., 18, 975 (1999)
Amin AS, Ragabb GH, Spectrochimica Acta Part A., 60, 2831 (2004)
Okoye NN, Nwokedi GIC, Ukwueze NN, Okoye FBC, Scientific Research and Essays., 2, 342 (2007)
Al-Momani IF, Journal of Pharmaceutical and Biomedical Analysis., 25, 751 (2001)
Sciacchitano CJ, Mopper B, Specchio JJ, Journal of Chromatography B., 657, 395 (1994)
Pajchel G, Tyski S, Journal of Chromatography A., 895, 27 (2000)
Coomber PA, Jefferies JP, Woodford JD, Analyst., 107, 1451 (1982)
Rodenbach MP, Hecq JD, Vanbeckbergen D, Jamart J, Galanti L, European Journal of Hospital Pharmacy., 12, 32 (2006)
Vieira DCM, Salgado HRN, Journal of Chromatographic Science., 49, 508 (2011)
Kelson EP, Phengsy PP, International Journal of Chemical Kinetics., 32, 760 (2000)
Vovk AI, Muraveva IV, Kukhar VP, Baklan VF, Russian Journal of General Chemistry., 70, 1108 (2000)
Jose TP, Nandibewoor ST, Tuwar SM, Journal of Solution Chemistry., 35, 47 (2006)
Leal JM, Garcia B, Domingo PL, Coordination Chemistry Reviews., 173 (1998)
Jose TP, Angadi MA, Salunke MS, Tuwar SM, Journal of Molecular Structure., 892, 121 (2008)
Sharanabasamma K, Angadi MA, Salunke MS, Tuwar SM, Ind. Eng. Chem. Res., 48(23), 10381 (2009)
Farokhi SA, Nandibewoor ST, Tetrahedron., 59, 7595 (2003)
Khan AAP, Mohd A, Bano S, Siddiqi KS, Journal of Diabetes Science and Technology., 5, 717 (2011)
Thabaj KA, Chimatadar SA, Nandibewoor ST, Progress in Reaction Kinetics and Mechanism., 33, 331 (2008)
Khan AAP, Mohd A, Bano S, Siddiqi KS, J & S Chemical., 5, 427 (2011)
Mucientes E, Poblete FJ, Rodriguez MA, Santiago F, Journal of Physical Organic Chemistry., 10, 662 (1997)
Tandon PK, Dhusia M, Sahgal S, J. Mol. Catal. A-Chem., 301(1-2), 146 (2009)
Zourab SM, Ezzo EM, Aila HJ, Salem JKJ, Journal of Diabetes Science and Technology., 24, 67 (2003)
Hassan RM, Ibrahim SM, Zaafarany IA, Fawzy A, Takagi HD, J. Mol. Catal. A-Chem., 344(1-2), 93 (2011)
Jose TP, Nandibewoor ST, Tuwar SM, Journal of Solution Chemistry., 35, 51 (2006)
Milazzo G, Caroll S, Tables of Standard Electrode Potential, Wiley, New York (1978)
Singh VN, Gangwar MC, Saxena BBL, Singh MP, Canadian Journal of Chemistry., 47, 1056 (1969)
Mendham J, Denney RC, Barnes JD, Thomas MJK, Vogel’s Text Book of Quantitati Ve Chemical Analysis, 6th ed., Pearson Education, Delhi, India, 466 (2003)
Weast RC, CRC Handbook of Chemistry and Physics, 49th ed., The Chemical Rubber Co., Ohio, .D-79 (1969)
Bent HE, French CL, Journal of the American Chemical Society., 63, 568 (1941)
Bhattacharya S, Benerjee P, Bulletin of the Chemical Society., 69, 3475 (1996)
Lancaster JM, Murray RSJ, Chemical Society Reviews A., 2755 (1971)
Rangappa KS, Raghavendra MP, Mahadevappa DS, Channegouda DJ, Organic Chemistry., 63, 531 (1998)
Weiss BA, in: Lewis ES (Ed.), Vestigation of Rates and Mechanisms of Reactions in Techniques of Chemistry, vol. 6, John Wiley and Sons Inc., New York, 421 (1974)
Khan AAP, Mohd A, Bano S, Siddiqi KS, Ind. Eng. Chem. Res., 50(17), 9883 (2011)
Khan AAP, Asiri AM, Azum N, Rub MA, Khan A, Al-Youbi AO, Ind. Eng. Chem. Res., 51(13), 4819 (2012)

[Referenced By]

[1] Brunton LL, Lazo JS, Parker KL, Goodman, Gilman, Thepharmacological Basis of therapeutics, 11th ed., McGraw-Hill, New York (2006)

[2] Jelinska A, Zajac M, Jakubowska M, Reaction Kinetics and Catalysis Letters., 73, 331 (2001)

[3] Dollery C, Therapeutic Drugs Second, 2nd ed., Churchill Livingstone, London UK. C135 (1999)

[4] Okamoto MP, Nakahiro RK, Chin A, Bedikian A, Gill MA, American Journal of Hospital Pharmacy., 51, 463 (1994)

[5] Murillo JA, Lemus JM, Garcia LF, Journal of Pharmaceutical and Biomedical Analysis., 12, 875 (1994)

[6] Bano S, Mohd A, Khan AAP, Siddiqi KS, Journal of Diabetes Science and Technology., 7, 1023 (2011)

[7] Salem H, Askal H, Journal of Pharmaceutical and Biomedical Analysis., 29, 347 (2002)

[8] Ayad MM, Shalaby AA, Abdellatef HE, Elsaid HM, Journal of Pharmaceutical and Biomedical Analysis., 18, 975 (1999)

[9] Amin AS, Ragabb GH, Spectrochimica Acta Part A., 60, 2831 (2004)

[10] Okoye NN, Nwokedi GIC, Ukwueze NN, Okoye FBC, Scientific Research and Essays., 2, 342 (2007)

[11] Al-Momani IF, Journal of Pharmaceutical and Biomedical Analysis., 25, 751 (2001)

[12] Sciacchitano CJ, Mopper B, Specchio JJ, Journal of Chromatography B., 657, 395 (1994)

[13] Pajchel G, Tyski S, Journal of Chromatography A., 895, 27 (2000)

[14] Coomber PA, Jefferies JP, Woodford JD, Analyst., 107, 1451 (1982)

[15] Rodenbach MP, Hecq JD, Vanbeckbergen D, Jamart J, Galanti L, European Journal of Hospital Pharmacy., 12, 32 (2006)

[16] Vieira DCM, Salgado HRN, Journal of Chromatographic Science., 49, 508 (2011)

[17] Kelson EP, Phengsy PP, International Journal of Chemical Kinetics., 32, 760 (2000)

[18] Vovk AI, Muraveva IV, Kukhar VP, Baklan VF, Russian Journal of General Chemistry., 70, 1108 (2000)

[19] Jose TP, Nandibewoor ST, Tuwar SM, Journal of Solution Chemistry., 35, 47 (2006)

[20] Leal JM, Garcia B, Domingo PL, Coordination Chemistry Reviews., 173 (1998)

[21] Jose TP, Angadi MA, Salunke MS, Tuwar SM, Journal of Molecular Structure., 892, 121 (2008)

[22] Sharanabasamma K, Angadi MA, Salunke MS, Tuwar SM, Ind. Eng. Chem. Res., 48(23), 10381 (2009)

[23] Farokhi SA, Nandibewoor ST, Tetrahedron., 59, 7595 (2003)

[24] Khan AAP, Mohd A, Bano S, Siddiqi KS, Journal of Diabetes Science and Technology., 5, 717 (2011)

[25] Thabaj KA, Chimatadar SA, Nandibewoor ST, Progress in Reaction Kinetics and Mechanism., 33, 331 (2008)

[26] Khan AAP, Mohd A, Bano S, Siddiqi KS, J & S Chemical., 5, 427 (2011)

[27] Mucientes E, Poblete FJ, Rodriguez MA, Santiago F, Journal of Physical Organic Chemistry., 10, 662 (1997)

[28] Tandon PK, Dhusia M, Sahgal S, J. Mol. Catal. A-Chem., 301(1-2), 146 (2009)

[29] Zourab SM, Ezzo EM, Aila HJ, Salem JKJ, Journal of Diabetes Science and Technology., 24, 67 (2003)

[30] Hassan RM, Ibrahim SM, Zaafarany IA, Fawzy A, Takagi HD, J. Mol. Catal. A-Chem., 344(1-2), 93 (2011)

[31] Jose TP, Nandibewoor ST, Tuwar SM, Journal of Solution Chemistry., 35, 51 (2006)

[32] Milazzo G, Caroll S, Tables of Standard Electrode Potential, Wiley, New York (1978)

[33] Singh VN, Gangwar MC, Saxena BBL, Singh MP, Canadian Journal of Chemistry., 47, 1056 (1969)

[34] Mendham J, Denney RC, Barnes JD, Thomas MJK, Vogel’s Text Book of Quantitati Ve Chemical Analysis, 6th ed., Pearson Education, Delhi, India, 466 (2003)

[35] Weast RC, CRC Handbook of Chemistry and Physics, 49th ed., The Chemical Rubber Co., Ohio, .D-79 (1969)

[36] Bent HE, French CL, Journal of the American Chemical Society., 63, 568 (1941)

[37] Bhattacharya S, Benerjee P, Bulletin of the Chemical Society., 69, 3475 (1996)

[38] Lancaster JM, Murray RSJ, Chemical Society Reviews A., 2755 (1971)

[39] Rangappa KS, Raghavendra MP, Mahadevappa DS, Channegouda DJ, Organic Chemistry., 63, 531 (1998)

[40] Weiss BA, in: Lewis ES (Ed.), Vestigation of Rates and Mechanisms of Reactions in Techniques of Chemistry, vol. 6, John Wiley and Sons Inc., New York, 421 (1974)

[41] Khan AAP, Mohd A, Bano S, Siddiqi KS, Ind. Eng. Chem. Res., 50(17), 9883 (2011)

[42] Khan AAP, Asiri AM, Azum N, Rub MA, Khan A, Al-Youbi AO, Ind. Eng. Chem. Res., 51(13), 4819 (2012)