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2013 | 15 | 3 | 55-60
Tytuł artykułu

Kinetic investigation of oxidation of aromatic anils by magnesium monoperoxyphthalate in aqueous acidic medium

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The kinetics of oxidation of aromatic anils to benzaldehyde and azobenzene by magnesium monoperoxyphthalate (MMPP) has been studied in aqueous acetic acid medium. The low dielectric constant of the medium facilitates the reactivity. It has been found that ionic strength of the reaction has no significant effect on rate. The added acrylonitrile has no effect on the reaction rate indicating the absence of free radical mechanism. The added Mn(II) decreases the rate of the reaction, which indicates the involvement of two-electron transfer. Highly negative ΔS# values indicate a structured transition state. The deviation of Hammett plot is noted and a non-linear concave downward curve is obtained for the anils with substituents in the aniline moiety. The observed break in the log kobs versus σ is attributed to the transition state whereas the non-linear concave upward curve is observed for the substituents in the benzaldehyde moiety and a non-linear concacve upward curve is observed for the substituents in the combination of aniline and benzaldehyde moiety and a suitable mechanism is proposed
Wydawca

Rocznik
Tom
15
Numer
3
Strony
55-60
Opis fizyczny
Daty
wydano
2013-09-01
online
2013-09-20
Twórcy
  • Sona College of Technology (Autonomous), Department of Chemistry, Salem – 636005, Tamilnadu, India
  • Sona College of Technology (Autonomous), Department of Chemistry, Salem – 636005, Tamilnadu, India, karunachemist@gmail.com
Bibliografia
  • 1. Brougham, P., Cooper, M.S., Cummerson, D.A., Heaney, H. & Thompson, N. (1987). Epoxidation studies of decalin-1, 4-dienones and related alcohols. Synthe., 1015-1017. DOI: 10.1055/s-1987-28153.[Crossref]
  • 2. Heaney, H. (1993). Oxidation reactions using magnesium monoperphthalate and urea hydrogen peroxide. AldrichimicaActa., 26, 35-45.
  • 3. Joao, F.S., Carvalho, M., Manuel Cruz Silva, M. & Luisa Sa e Melo. (2009). Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate. J. Tetrahed., 65, 2773-2781. DOI: 10.1016/j.tet.2009.01.100.[Crossref]
  • 4. Ali, M.H. & Stevens, W.C. (1997). Sulfides to sulfoxides on silica gel supported magnesium monoperoxyphthalate (MMPP) in methylene chloride. Synthe., 764-768.
  • 5. Enrico Baciocchi, Osvaldo Lanzalunga. & Andrea Lapi. (1995). Formation of quinines in the iron porphyrin catalyzed oxidation of benzene and alkylbenzenes by magnesium monoperoxyphthalate. Tetrahedron lett., 36, 3547-3548. DOI: 10.1016/0040-4039(95)00554-P[Crossref]
  • 6. Simon J. Hayes, David W. Knight, Andrew W.T. Smith. & Mark J.O’Halloran. (2010). On the curious oxidations of 2-furylethanols. Tetrahedron lett., 51, 720-723. DOI: 10.1016/j.tetlet.2009.11.119.[WoS][Crossref]
  • 7. Lisa Y. Wu, Joseph K. Choi, Krit Y. Hatton. & Clifford E. Berkman. (2010). A simple method for the oxidation of a-amino acid esters to a-oximino esters. Tetrahedron lett., 51, 402-403. DOI: 10.1016/j.tetlet.2009.11.045.[Crossref]
  • 8. Raja, M. & Karunakaran, K. (2012). meso-Tetraphenylporphyriniron( III) chloride catalyzed oxidation of aniline and its substituents by magnesium monoperoxyphthalate in aqueous acetic acid medium. Pol. J. Chem. Tech., in press.
  • 9. Karthikeyan, G., Elango, K.P., Karunakaran, K. & Balasubramanian, A. (1998). Kinetics and mechanism of oxidation of aromatic anils by quinolinium chlorochromate. OxidCommun, 21(1), 51-54.
  • 10. Umesh, N., Ramesh, S. & Dodwad, S.S. (1997). Kinetics and mechanism of acid bromate oxidation of 2-hydroxy-1-naphthalidene anil. Asian J. Chem., 9 (1), 58-62.
  • 11. Karunakaran, K., Nagarajan, S., Kanagavel, D., Jegadish, T.N., Palanisamy, P.N. & Elango, K.P. (1997). Interactive free energy relationship on the oxidation of aromatic anils by phenyliodoso acetate. Oxid Commun., 29 (4), 576.
  • 12. Ramalingam, G. & Jayanthi, S. (2007). Mechanistic investigation of oxidation of aromatic anils by isonicotinium dichromate in acetic medium. A Kinetic Study. Transit Met Chem Springer 2007, 32, 475-480. DOI: 10.1007/s11243-007-0190-x.[Crossref][WoS]
  • 13. Lide, David R., ed. (2006). CRC Handbook of Chemistryand Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
  • 14. Venkatesh, R. & Karunakaran, K. (2013). Kinetic investigation of oxidation of aromatic anils by potassium peroxymonosulfate in aqueous acidic medium. Int. J. Chem. Kinet., 2013 in press.[WoS]
  • 15. Karunakaran, C. & Palanysamy, P.N. (2001). Autocatalysis in the sodium perborate oxidation of aniline in acetic acid-ethylene glycol. J. Mol. Catal. A-Chem., 172, 9-17. DOI: Org/10.1016/s 1381- 1169(01)00113-3.
  • 16. Chandramohan, G., Kalyansundharam, S. & Renganathan, R. (2002). Oxidation of indole-3-acetic acid by peroxomonosulphate: A kinetic and mechanic study. Int. J. Chem. Kinet., 34, 569. DOI: 10.1002/kin.10060.[Crossref]
  • 17. Kutti rani, S., Nirmal kumar, S., Crystal Y Wilson., Gopi, A. & Eswaramoorthy, D. (2009). Oxidation of vanillin by peroxomonosulphate-thermodynamic and kinetic investigation. J. Ind. Eng. Chem., 15, 898-901. DOI: 10.1016/j.jiec.2009.09.020.[Crossref]
  • 18. Karthikeyan, G., Elango, K.P. & Karunakaran K. (1997). Correlation analysis of reactivity in the oxidation of aromatic anils by pyridinium flurochromate. J. Indian Chem. Soc., 74(10), 798-799.
  • 19. Hammett, Louis, P. (1937). Hammett equation. J. Am. Chem. Soc., 59, 96. DOI:10.1021/ja01280a022.[Crossref]
  • 20. Hoffmann, J., Klicnar, J., Sterba, V. & Vecera M. Coll. (1970). Deviations from hammett correlations-concave down Y. Czech. Chem. Commun., 35, 1387, http://www.docstoc.com/docs/28281427/Hammett-correlations-and-their-applicationsin-elucidating [Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_pjct-2013-0044
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