Journal of Chemical Sciences

, Volume 114, Issue 1, pp 55–60 | Cite as

An analysis on the transmission of electron density through sulphur atoms in the quaternization reactions of benzothiazoles

  • B. K. Mishra
  • Sabita Patel


The kinetics of quaternization of a number of 2-substituted benzothiazoles with alkyl iodides and phenacyl bromide have been studied in nitrobenzene. The order of reactivity of different substituted benzothiazoles has been found to be -H > NO2 > Cl. The relative reactivity of 2-amino and 2-methyl derivatives has been ascribed to a solvation phenomenon. The analysis of rho values from the Hammett equation suggests two possible routes for the transmission of electron density.


Quaternization reaction benzothiazole Hammett equation 


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  1. 1.
    Mishra P, Mishra B K and Behera G B 1988Indian J. Chem. A27 889Google Scholar
  2. 2.
    Mishra B K, Sharma A and Behera G B 1989Int. J. Chem. Kinet. 21 439CrossRefGoogle Scholar
  3. 3.
    Mishra P K, Mishra B K and Behera G B 1991Int. J. Chem. Kinet. 23 639CrossRefGoogle Scholar
  4. 4.
    Mishra P K, Mishra B K and Behera G B 1992Int. J. Chem. Kinet. 24 533CrossRefGoogle Scholar
  5. 5.
    Senapati S, Dash P K, Mishra B K and Behera G B 1995Indian J. Chem. A34 278Google Scholar
  6. 6.
    Mishra R K, Hota S, Mishra B K and Behera G B 1998Indian J. Chem. A37 200Google Scholar
  7. 7.
    Patel N, Hota S, Mishra B K and Behera G B 2000Indian J. Chem. A39 763Google Scholar
  8. 8.
    Menschutkin N 1890Z. Phys. Chem. 5 589Google Scholar
  9. 9.
    Deady L W 1973Aust. J. Chem. 19 1949CrossRefGoogle Scholar
  10. 10.
    Grob C A and Schlageter 1974Helv. Chem. Acta 57 509CrossRefGoogle Scholar
  11. 11.
    Behera G B, Kar J N, Acharya R C and Rout M K 1973J. Org. Chem. 38 2164; BeheraGB and Sharma A 1979Bull. Chem. Soc. Jpn 52 604CrossRefGoogle Scholar
  12. 12.
    Bhargava P N and Baliga B J 1958J. Indian Chem. Soc. 35 807Google Scholar
  13. 13.
    Konig W 1968Ber. Dtsch. Chem. Ges. 61 2065Google Scholar
  14. 14.
    Browit E I and Prones H 1967J. Org. Chem. 32 3560CrossRefGoogle Scholar
  15. 15.
    Riddiel and Bunger (eds) 1970Organic solvents: Physical properties and methods of purification (London: Wiley Interscience) vol 2, p 790Google Scholar
  16. 16.
    Joule J A and Smith G F 1978 InHeterocyclic chemistry (London: Van Nostrand Reinhold)Google Scholar
  17. 17.
    Jaffe H H 1953Chem. Rev. 53 191CrossRefGoogle Scholar
  18. 18.
    Davis F A, Kaminishi J M, Kinger E W and Freilich H S 1975J. Am. Chem. Soc. 97 7085CrossRefGoogle Scholar
  19. 19.
    Kajimoto O, Koboyashi M and Feuno T 1973Bull. Chem. Soc. Jpn 46 2316CrossRefGoogle Scholar
  20. 20.
    Deady L W and Stillman D C 1976Aust. J. Chem. 29 1745CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2002

Authors and Affiliations

  1. 1.Centre of Studies in Surface Science and Technology, Department of ChemistrySambalpur UniversityJyoti ViharIndia

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