Skip to main content

Advertisement

SpringerLink
Log in

FTIR Study of Hydrogen Bonding Between Acrylic Esters and Alcohols

  • Original Paper
  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Hydrogen bonding between acrylic esters and alcohols has been studied in carbon tetrachloride by using the FTIR spectroscopic method. Utilizing the Nash method, the formation constant of the 1:1 complexes has been calculated. The formation constant and Gibbs energy change values vary with alcohol and ester chain length, which suggests that the proton donating ability of alcohols is in the order: 1-propanol < 1-butanol < 1-pentanol, and the accepting ability of acrylic esters is in the order: methyl methacrylate < ethyl methacrylate < butyl methacrylate.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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. Schildknecht, C.E.: Vinyl and Related Polymers. Wiley, New York (1977)

    Google Scholar 

  2. Liu, Q., Zheng, J.P., Fang, D.J.: Solvent effects on infrared spectra of methyl methacrylate. Spectrosc. Lett. 37, 225–233 (2004)

    Article  CAS  Google Scholar 

  3. Zheng, J.P., Liu, Q., Zhang, H., Fang, D.J.: Solvent effect on infrared spectra of methyl methacrylate in CCl4 /C6H14, CHCl3/C6H14 and C2H5OH/C6H14 binary solvent systems. Spectrochim. Acta 60A, 3119–3123 (2004)

    CAS  Google Scholar 

  4. Rosenberg, A.S., Smith, H.F.: Relation between molecular structure and hydrogen bonding of aliphatic alcohols and aliphatic esters as determined by infrared spectroscopy. Part V. J. Chem. Soc. 5395–5399 (1963)

  5. Dulce G., Farra, M., Teixeira-Dias, J.J.C., Fausto, R.: Hydrogen bonding involving α, β-unsaturated carboxylic esters and substituted phenols: an infrared study. J. Mol. Struct. 263, 87–94 (1991)

    Article  Google Scholar 

  6. Gisela S.F.D., Pouchan, C., Teixeira-Dias, J.J.C., Fausto, R.: Hydrogen bonding between substituted phenols and CH3COOCH3 or CH2ClCOOCH3: an FTIR spectroscopic study. Spectrosc. Lett. 26, 913–922 (1993)

    Google Scholar 

  7. Vanderheyden, L., Zeegers-Huyskens, Th.: Infrared and Raman study of the interaction between methyl acetate and phenol derivatives. J. Mol. Liq. 25, 1–11 (1983)

    Article  CAS  Google Scholar 

  8. Sivagurunathan, P., Dharmalingam, K., Ramachandran, K.: Solvent effects on hydrogen bonding between ethyl methacrylate and 1-butanol. Z. Phys. Chem. 219, 1385–1390 (2005)

    CAS  Google Scholar 

  9. Weissberger, A.: Technique of Organic Chemistry. Wiley Interscience, New York (1970)

    Google Scholar 

  10. Riddick, J.R., Bunger, W.B.: Organic Solvents. Wiley Interscience, New York (1970)

    Google Scholar 

  11. Vogel, A. I.: Text Book of Practical Organic Chemistry, 3rd edition. Longman, London (1957)

    Google Scholar 

  12. Kirsch, J.L., Coffin, D.R.: Infrared and nuclear magnetic resonance studies of hydrogen bonding in aliphatic alcohols systems. J. Phys. Chem. 80, 2448–2451 (1976)

    Article  CAS  Google Scholar 

  13. Ibbitson, D.A., Moore, L.F.: Association of n-alcohols in non-polar solvents. Part 1. The dielectric polarizations, apparent dipole moments and near-infrared spectra of n-alcohols in carbon tetrachloride and cyclohexane. J. Chem. Soc. (B) 76–80 (1967)

    Google Scholar 

  14. Van Ness, H.C., Winkle, J.V., Richtol, H.H., Hollinger, H.S.: Infrared spectra and thermodynamics of alcohol-hydrocarbon systems. J. Phys. Chem. 71, 1483–1494 (1967)

    Article  Google Scholar 

  15. Liddel, U., Becker, E.D.: Infrared spectroscopic studies of hydrogen bonding in methanol, ethanol and t-butanol. Spectrochim. Acta 10, 70–84 (1957)

    Article  CAS  Google Scholar 

  16. Sivagurunathan, P., Dharmalingam, K., Ramachandran, K.: Molecular interaction studies of acrylic esters with 1-alcohols. Spectrochim. Acta 64A, 127–129 (2006)

    CAS  Google Scholar 

  17. Nyquist, R.A., Streck, R.: Infrared solution study of alkyl acrylates and alkyl methacrylates in CHCl3 and /or CCl4 solutions. Vib. Spectrosc. 8, 71–85 (1994)

    Article  CAS  Google Scholar 

  18. Nash C.P.: The calculation of equilibrium constants from spectro-photometric data. J. Phys. Chem. 64, 950–953 (1960)

    CAS  Google Scholar 

  19. Vinogradov, C.R.H.: Hydrogen Bonding. Van Nostrand Reinhold Company, New York (1971)

    Google Scholar 

  20. Chandra., A.K., Basu, S.: Hydrogen bonds 1. Trans. Faraday Soc. 56, 632–637 (1960)

    Article  CAS  Google Scholar 

  21. Dash, S.K., Das, J.K., Swain, B.B.: Dielectric studies of hydrogen bonded complexes — Methyl isobutyl ketone (MIBK) with aliphatic alcohols. Indian J. Pure Appl. Phys. 38, 791–796 (2000)

    CAS  Google Scholar 

  22. Singh, A., Saxena, M.C.: An equation to calculate the equilibrium constant of 1:1 complexes from dielectric relaxation measurements. J. Mol. Liq. 25, 81–90 (1983)

    Article  CAS  Google Scholar 

  23. Singh, A., Misra, R., Shukla, J.P., Saxena, M.C.: Evaluation of the thermodynamic parameters for association process of hydrogen bond complexes from the dielectric relaxation measurements. J. Mol. Liq. 26, 29–40 (1983)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Physics, Annamalai University, Annamalai Nagar, Tamilnadu, 608002, India

    P. Sivagurunathan, K. Dharmalingam & K. Ramachandran

Authors
  1. P. Sivagurunathan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. Dharmalingam
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Ramachandran
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Sivagurunathan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sivagurunathan, P., Dharmalingam, K. & Ramachandran, K. FTIR Study of Hydrogen Bonding Between Acrylic Esters and Alcohols. J Solution Chem 35, 1467–1475 (2006). https://doi.org/10.1007/s10953-006-9076-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-006-9076-3

Keywords

Search

Navigation