Skip to main content
SpringerLink
Log in

Facile chlorination of acetophenone by chloramine-T in the cationic micellar phase

  • Organic
  • Published:
Proceedings of the Indian Academy of Sciences - Chemical Sciences Aims and scope Submit manuscript

Abstract

The chlorination of acetophenone by chloramine-T (cat) has been catalysed by added detergents, sodium laurylsulphate (NaLS) and cetyltrimethylammonium bromide (ctab). Phenacyl chloride is the exclusive product of the reaction and the % yield of the product is greater in the cationic micellar phase indicating facile chlorination in this media (even in the absence of the mineral acid). Using Piszkiewicz’s treatment, the positive cooperativity for the micellar catalysed reactions has been calculated. At the cationic micellar phase ofctab, the interaction between ammonium ion and phenyl and methylene groups probably leads to greater stabilisation than the simple hydrophobic association encountered in the micelle interior of NaLS.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Balasubramanian V and Thiagarajan V 1976Aust. J. Chem. 29 1449

    CAS  Google Scholar 

  • Balasubramanian V and Thiagarajan V 1975Int. J. Chem. Kinet. 7 605

    Article  CAS  Google Scholar 

  • Balasubramanian D, Ganesh K N and Mitra P 1982J. Phys. Chem. 86 4291

    Article  Google Scholar 

  • Behme M T A, Fullington J G, Noel R and Cordes E H 1965J. Am. Chem. Soc. 87 266

    Article  CAS  Google Scholar 

  • Dennis Piszkiewicz 1977J. Am. Chem. Soc. 99 1550

    Article  Google Scholar 

  • Duynstee E F G and Grunwald E 1959J. Am. Chem. Soc. 81 4540

    Article  CAS  Google Scholar 

  • Fendler F H, Fendler E J, Infanta G A, Shih P S and Patterson L K 1975J. Am. Chem. Soc. 97 89

    Article  CAS  Google Scholar 

  • Higuchi T and Hussain A 1967J. Chem. Soc. 549

  • Menger F M and Bonicamp J M 1981J. Am. Chem. Soc. 103 2140

    Article  CAS  Google Scholar 

  • Mueller N 1973in Reaction kinetics in micelles (ed) E G Cordes, (New York: Plenum Press) p. 1–23

    Google Scholar 

  • Pryde L R and Soper F G 1931J. Am. Chem. Soc. 53 1510

    Google Scholar 

  • Raghavan P S, Srinivasan V S and Venkatasubramanian N 1980Indian. J. Chem. A19 322

    Google Scholar 

  • Raghunathan V, Raghavan P S, Vaidyanathan K and Srinivasan V S 1982Proc. Indian Acad. Sci. (Chem. Sci.) 91 371

    Google Scholar 

  • Rengarajan K, Vaidyanathan K, Srinivasan V S and Venkatasubramanian N 1980Indian J. Chem. A19 79

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Ramakrishna Mission, Vivekananda College, Mylapore, 600 004, Madras, India

    P S Raghavan & Vangalur S Srinivasan

Authors
  1. P S Raghavan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vangalur S Srinivasan
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Raghavan, P.S., Srinivasan, V.S. Facile chlorination of acetophenone by chloramine-T in the cationic micellar phase. Proc. Indian Acad. Sci. (Chem. Sci.) 93, 849–854 (1984). https://doi.org/10.1007/BF02866347

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02866347

Keywords

Search

Navigation