Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach
The kinetics of oxidation of phenylpropanolamine (PPA) with sodium N-bromobenzenesulfonamide or bromamine-B (BAB) has been investigated in alkaline medium at 308 K. The oxidation reaction obeys the rate law, – d[BAB]/dt = k [BAB] [PPA]x [OH-], where x is less than unity. The variation of ionic stren...
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Wiley
2008-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2008/348482 |
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| author | Ningegowda Prasad Kikkeri N. Mohana |
| author_facet | Ningegowda Prasad Kikkeri N. Mohana |
| author_sort | Ningegowda Prasad |
| collection | DOAJ |
| description | The kinetics of oxidation of phenylpropanolamine (PPA) with sodium N-bromobenzenesulfonamide or bromamine-B (BAB) has been investigated in alkaline medium at 308 K. The oxidation reaction obeys the rate law, – d[BAB]/dt = k [BAB] [PPA]x [OH-], where x is less than unity. The variation of ionic strength of the medium, addition of the reduction product, benzenesulfonamide, and chloride ion had no pronounced effect on the reaction rate. Decrease of dielectric permittivity of the medium by increasing the CH3CN content increased the rate. The reaction was studied at different temperatures and the activation parameters have been evaluated from the Arrhenius plot. The stiochiometry of the reaction was found to be 1:1, and the oxidation product of phenylpropanolamine was identified as benzaldehyde and ethylideneamine. The rate decreased in D2O medium and the normal isotope effect k' (H2O) / k' (D2O) is 2.18. Proton inventory studies have been made in H2O - D2O mixtures. Formation and decomposition constant of BAB-PPA complexes in the reaction scheme have been determined. The conjugate acid, C6H5SO2NHBr is assumed to be the reactive species. The proposed mechanism and the derived rate law are consistent with the observed experimental results. |
| format | Article |
| id | doaj-art-468d4f046a174b04964fa9699a3c342f |
| institution | Kabale University |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2008-01-01 |
| publisher | Wiley |
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| series | E-Journal of Chemistry |
| spelling | doaj-art-468d4f046a174b04964fa9699a3c342f2025-02-03T07:25:11ZengWileyE-Journal of Chemistry0973-49452090-98102008-01-015233134110.1155/2008/348482Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic ApproachNingegowda Prasad0Kikkeri N. Mohana1Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, IndiaThe kinetics of oxidation of phenylpropanolamine (PPA) with sodium N-bromobenzenesulfonamide or bromamine-B (BAB) has been investigated in alkaline medium at 308 K. The oxidation reaction obeys the rate law, – d[BAB]/dt = k [BAB] [PPA]x [OH-], where x is less than unity. The variation of ionic strength of the medium, addition of the reduction product, benzenesulfonamide, and chloride ion had no pronounced effect on the reaction rate. Decrease of dielectric permittivity of the medium by increasing the CH3CN content increased the rate. The reaction was studied at different temperatures and the activation parameters have been evaluated from the Arrhenius plot. The stiochiometry of the reaction was found to be 1:1, and the oxidation product of phenylpropanolamine was identified as benzaldehyde and ethylideneamine. The rate decreased in D2O medium and the normal isotope effect k' (H2O) / k' (D2O) is 2.18. Proton inventory studies have been made in H2O - D2O mixtures. Formation and decomposition constant of BAB-PPA complexes in the reaction scheme have been determined. The conjugate acid, C6H5SO2NHBr is assumed to be the reactive species. The proposed mechanism and the derived rate law are consistent with the observed experimental results.http://dx.doi.org/10.1155/2008/348482 |
| spellingShingle | Ningegowda Prasad Kikkeri N. Mohana Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach E-Journal of Chemistry |
| title | Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach |
| title_full | Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach |
| title_fullStr | Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach |
| title_full_unstemmed | Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach |
| title_short | Mechanistic Investigation of Oxidation of Phenylpropanolamine with N-Bromobenzenesulfonamide in Alkaline Medium: A Kinetic Approach |
| title_sort | mechanistic investigation of oxidation of phenylpropanolamine with n bromobenzenesulfonamide in alkaline medium a kinetic approach |
| url | http://dx.doi.org/10.1155/2008/348482 |
| work_keys_str_mv | AT ningegowdaprasad mechanisticinvestigationofoxidationofphenylpropanolaminewithnbromobenzenesulfonamideinalkalinemediumakineticapproach AT kikkerinmohana mechanisticinvestigationofoxidationofphenylpropanolaminewithnbromobenzenesulfonamideinalkalinemediumakineticapproach |