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Palladium(II)-catalyzed oxidation of tranexamic acid by bromamine-B in alkaline medium and uncatalyzed reaction in acid medium: A study of kinetic and mechanistic chemistry

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Title: Palladium(II)-catalyzed oxidation of tranexamic acid by bromamine-B in alkaline medium and uncatalyzed reaction in acid medium: A study of kinetic and mechanistic chemistry
Authors: Puttaswamy pswamy_chem@yahoo.com, Sukhdev, Anu1, Shubha, J.P.1
Source: Journal of Molecular Catalysis A: Chemistry. Nov2010, Vol. 332 Issue 1/2, p113-121. 9p.
Subjects: Palladium catalysts, Chemical kinetics, Antifibrinolytic agents, Oxidation-reduction reaction, Temperature effect, Activation (Chemistry)
Abstract: Abstract: Tranexamic acid (TA) possess antifibrinolytic properties and finds extensive applications in pharmaceuticals. Its oxidation-kinetic study is of much significance in understanding the mechanistic profile of TA in biological systems. In this context, a systematic kinetic study of palladium(II) (Pd(II)) catalyzed oxidation of TA by sodium N-bromobenzenesulfonamide or bromamine-B (BAB) in alkaline medium and uncatalyzed reaction in perchloric acid medium at 303K was investigated. In acid medium, the reaction exhibits a first-order dependence of rate on [BAB]o and less than unity order dependence on [TA]o. The reaction rate shows inverse less than unity order dependence with respect to [H+]. In alkaline medium, the reaction shows first-order dependence on both [BAB]o and [Pd(II)] and zero-order with respect to [TA]o. The order with respect to [OH−] is less than unity. Activation parameters have been evaluated. The oxidation reactions are nearly 10-fold faster in acid medium in comparison with alkaline medium. In alkaline medium, the Pd(II) catalyzed reactions are about 6-fold faster than the uncatalyzed reaction. Further, the catalytic constant (K C ) has been calculated at different temperatures and activation parameters with respect to Pd(II) catalyst have also been evaluated. The conjugate acid C6H5SO2NHBr and the anion C6H5SO2N−Br of BAB have been postulated as the reactive oxidizing species in acid and alkaline media, respectively. The proposed mechanisms and derived rate laws are in agreement with the observed kinetics. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Molecular Catalysis A: Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Palladium(II)-catalyzed oxidation of tranexamic acid by bromamine-B in alkaline medium and uncatalyzed reaction in acid medium: A study of kinetic and mechanistic chemistry
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  Data: <searchLink fieldCode="AR" term="%22Puttaswamy%22">Puttaswamy</searchLink><i> pswamy_chem@yahoo.com</i><br /><searchLink fieldCode="AR" term="%22Sukhdev%2C+Anu%22">Sukhdev, Anu</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Shubha%2C+J%2EP%2E%22">Shubha, J.P.</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Catalysis+A%3A+Chemistry%22">Journal of Molecular Catalysis A: Chemistry</searchLink>. Nov2010, Vol. 332 Issue 1/2, p113-121. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Palladium+catalysts%22">Palladium catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+kinetics%22">Chemical kinetics</searchLink><br /><searchLink fieldCode="DE" term="%22Antifibrinolytic+agents%22">Antifibrinolytic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Oxidation-reduction+reaction%22">Oxidation-reduction reaction</searchLink><br /><searchLink fieldCode="DE" term="%22Temperature+effect%22">Temperature effect</searchLink><br /><searchLink fieldCode="DE" term="%22Activation+%28Chemistry%29%22">Activation (Chemistry)</searchLink>
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  Label: Abstract
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  Data: Abstract: Tranexamic acid (TA) possess antifibrinolytic properties and finds extensive applications in pharmaceuticals. Its oxidation-kinetic study is of much significance in understanding the mechanistic profile of TA in biological systems. In this context, a systematic kinetic study of palladium(II) (Pd(II)) catalyzed oxidation of TA by sodium N-bromobenzenesulfonamide or bromamine-B (BAB) in alkaline medium and uncatalyzed reaction in perchloric acid medium at 303K was investigated. In acid medium, the reaction exhibits a first-order dependence of rate on [BAB]o and less than unity order dependence on [TA]o. The reaction rate shows inverse less than unity order dependence with respect to [H+]. In alkaline medium, the reaction shows first-order dependence on both [BAB]o and [Pd(II)] and zero-order with respect to [TA]o. The order with respect to [OH−] is less than unity. Activation parameters have been evaluated. The oxidation reactions are nearly 10-fold faster in acid medium in comparison with alkaline medium. In alkaline medium, the Pd(II) catalyzed reactions are about 6-fold faster than the uncatalyzed reaction. Further, the catalytic constant (K C ) has been calculated at different temperatures and activation parameters with respect to Pd(II) catalyst have also been evaluated. The conjugate acid C6H5SO2NHBr and the anion C6H5SO2N−Br of BAB have been postulated as the reactive oxidizing species in acid and alkaline media, respectively. The proposed mechanisms and derived rate laws are in agreement with the observed kinetics. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Molecular Catalysis A: Chemistry is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.molcata.2010.09.005
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        Type: general
      – SubjectFull: Chemical kinetics
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      – SubjectFull: Antifibrinolytic agents
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      – SubjectFull: Oxidation-reduction reaction
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      – SubjectFull: Temperature effect
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      – SubjectFull: Activation (Chemistry)
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      – TitleFull: Palladium(II)-catalyzed oxidation of tranexamic acid by bromamine-B in alkaline medium and uncatalyzed reaction in acid medium: A study of kinetic and mechanistic chemistry
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              Text: Nov2010
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