Skip to main content
SpringerLink
Log in

Influence of solvents on the -OH and stretching frequencies of benzoin and methyl mandelatestretching frequencies of benzoin and methyl mandelate

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Abstract

The influence of solvents on the intramolecular hydrogen bond in benzoin and methyl mandelate is studied using infrared spectroscopy. Non-oxygenated solvents could not break the chelation but could shift the OH frequencies to a small extent. Oxygenated solvents like diethyl ether, acetone and dioxan could break the chelation and form intermolecular hydrogen bonds. The relative intensities of the bands of intra and intermolecular hydrogen bonds gave an indication of the donor ability of these solvents, which is linked with their capacity to break the intramolecular hydrogen bonding. Making use of the symmetry numbers of the OH band, the order of the interacting abilities of the oxygenated solvents in breaking the chelation is ascertained and explained.

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

  1. Suryanarayana, I., Swamy, A. S. R., Subrahmanyam, B., and Rao, N. V. S.,Curr. Sci. 44 49 (1975).

    Google Scholar 

  2. Weissberger, A., Proskauer, P., Riddick, J. R., and Troops, E. E.,Techniques of Organic Chemistry, Vol. VII.,Organic Solvents, Interscience, Inc., New York, Pages 367, 372 381, 411, 435 (1955).

    Google Scholar 

  3. Subrahmanyam, B. and Rao N. V. S.,Proc. Indian Acad. Sci. 80 97 (1974).

    Google Scholar 

  4. Bellamy, L. J. and Hallam, H. E.,Trans. Farad. Soc. 55 22 (1959).

    Google Scholar 

  5. Rao, C. N. R.,Chemical applications of infrared spectroscopy, Academic Press, New York, p. 208.

  6. Osawa, E., Kitamura, K. and Yoshida, Z.,J. Amer. Chem. Soc. 87 3814 (1967).

    Article  Google Scholar 

  7. Pimentel, G. C. and McClellan.,The Hydrogen Bond, W. H. Freeman and Co., San Francisco, p. 91 (1960).

    Google Scholar 

  8. Mori, N., Tanaka, Y. and Tsuzuki, Y.,Bull Chem. Soc., Japan,39 1490 (1966).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Osmania University, 500007, Hyderabad

    I. Suryanarayana, B. Subrahmanyam & N. V. Subba Rao F.A.Sc.

Authors
  1. I. Suryanarayana
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. Subrahmanyam
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. V. Subba Rao F.A.Sc.
    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

Suryanarayana, I., Subrahmanyam, B. & Subba Rao, N.V. Influence of solvents on the -OH and stretching frequencies of benzoin and methyl mandelatestretching frequencies of benzoin and methyl mandelate. Proc. Indian Acad. Sci. 82, 55–64 (1975). https://doi.org/10.1007/BF03046698

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03046698

Keywords

Search

Navigation