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FTIR Spectroscopy of Intermolecular Interactions of Ethers with Methanol: Cooperativity Effect

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Abstract

FTIR spectral analysis of solvation effects on the frequencies of O–H stretching vibrations of methanol complexes with linear (diethyl ether, di-n-butyl ether, and diglyme) and cyclic ethers (1,4-dioxane, 12-crown-4, 15-crown-5, and 18-crown-6) was carried out. The comparative analysis of the influence of solvation effects on the frequencies of O–H groups of methanol in aprotic solvents for both free and bound molecules with ethers (B) had been performed. Complexes in proton-donor solvents as well as in chloroform were investigated to quantify the change in the strength of X–H···B (where X = O) hydrogen bonds due to cooperative interactions. The influences of structure and size of the ether cycle on the contribution of the cooperativity effect of methanol with ethers are discussed.

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References

  1. Harris, J.M., Zalipsky, S.: Poly(ethylene glycol). ACS Symposium Series. American Chemical Society, Washington (1997)

    Book  Google Scholar 

  2. Ren, W., Qiao, Z., Wang, H., Zhu, L., Zhang, L.: Flavonoids: promising anticancer agents. Med. Res. Rev. 23(4), 519–534 (2003)

    Article  CAS  Google Scholar 

  3. Kwon, G.S.: Polymeric micelles for delivery of poorly water-soluble compounds. Crit. Rev. Ther. Drug Carr. Syst. 20(5), 357–403 (2003)

    Article  CAS  Google Scholar 

  4. Cheng, H.W., Rustenholtz, A., Porter, R.A., Ye, X.R., Wai, C.M.: Partition coefficients and equilibrium constants of crown ethers between water and organic solvents determined by proton nuclear magnetic resonance. J. Chem. Eng. Data 49(3), 594–598 (2004)

    Article  CAS  Google Scholar 

  5. Servaes, K., De Houwer, S., Görller-Walrand, C., Binnemans, K.: Spectroscopic properties of uranyl crown ether complexes in non-aqueous solvents. Phys. Chem. Chem. Phys. 6(11), 2946–2950 (2004)

    Article  CAS  Google Scholar 

  6. Matin, M.R., Katsumoto, Y., Matsuura, H., Ohno, K.: Hydration of short-chain poly(oxyethylene) in carbon tetrachloride: an infrared spectroscopic study. J. Phys. Chem. B 109(42), 19704–19710 (2005)

    Article  CAS  Google Scholar 

  7. Goutev, N., Matsuura, H.: Hydrogen bonding in chloroform solutions of ethylenedioxy ethers. Spectroscopic evidence of bifurcated hydrogen bonds. J. Phys. Chem. A 105(19), 4741–4748 (2001)

    Article  CAS  Google Scholar 

  8. Barannikov, V.P., Guseinov, S.S.: Effect of solvent polarity on enthalpies of solvation of ethylene oxide oligomers. J. Chem. Eng. Data. 65(5), 2784–2789 (2020). https://doi.org/10.1021/acs.jced.0c00098

    Article  CAS  Google Scholar 

  9. Barannikov, V.P., Guseynov, S.S., Vyugin, A.I.: Effect of electrostatic interaction on thermochemical behavior of 12-crown-4 ether in various polar solvents. Thermochim. Acta 499(1–2), 61–64 (2010)

    Article  CAS  Google Scholar 

  10. Barannikov, V.P., Guseinov, S.S.: Thermodynamic functions of solvation of 1,4-dioxane in various solvents at 298.15 K. Russ. J. Phys. Chem. A 88(2), 254–258 (2014)

    Article  CAS  Google Scholar 

  11. Barannikov, V.P., Guseynov, S.S., Vyugin, A.I.: Enthalpies of solvation of 1,4,7,10,13,16-hexaoxacyclooctadecane in solvents. J. Chem. Thermodyn. 36(4), 277–280 (2004)

    Article  CAS  Google Scholar 

  12. Nunes, N., Reis, M., Moreira, L., Elvas-Leitao, R., Martins, F.: Solution enthalpies of 1,4-dioxane: study of solvent effects through quantitative structure-property relationships. Thermochim. Acta 574, 85–87 (2013)

    Article  CAS  Google Scholar 

  13. Reis, M., Nunes, N., Elvas-Leitão, R., Martins, F.: Use of quantitative structure-property relationships to study the solvation process of 18-crown-6. Thermochim. Acta 604, 140–144 (2015)

    Article  CAS  Google Scholar 

  14. Jóźwiak, M.: Thermochemical behavior of crown ethers in the mixtures of water with organic solvents. Part VIII. Hydrophobic hydration and preferential solvation of 1,4-dioxane in {(1–x)amide + xH2O at T = 298.15 K. J. Chem. Thermodyn. 39(3), 433–437 (2007)

    Article  Google Scholar 

  15. Jóźwiak, M.: Thermochemical behaviour of crown ethers in the mixtures of water with organic solvents. Part IX. Effect of base-acid properties of {(1–x) AN + xH2O on the solution enthalpy of cyclic ethers in this mixed solvent at T = 298.15 K. J. Chem. Thermodyn. 41(4), 522–524 (2009)

    Article  Google Scholar 

  16. Jóźwiak, M.: The effect of properties of water-organic solvent mixtures on the solvation enthalpy of 12-crown-4, 15-crown-5, 18-crown-6 and benzo-15-crown-5 ethers at 298.15 K. Thermochim. Acta 417(1), 31–41 (2004)

    Article  Google Scholar 

  17. Jóźwiak, M.: Effect of Base–acid properties of mixtures of ethanol with water on the enthalpy of solution of cyclic ethers in these mixtures at T = 298.15 K. J. Solution Chem. 46(1), 234–246 (2017)

    Article  Google Scholar 

  18. Solomonov, B.N., Novikov, V.B., Varfolomeev, M.A., Klimovitskii, A.E.: Calorimetric determination of hydrogen-bonding enthalpy for neat aliphatic alcohols. J. Phys. Org. Chem. 18(11), 1132–1137 (2005)

    Article  CAS  Google Scholar 

  19. Varfolomeev, M.A., Abaidullina, D.I., Klimovitskii, A.E., Solomonov, B.N.: Solvent effect on stretching vibration frequencies of the N–H and O–H groups of diphenylamine and phenol in complexes with various proton acceptors: cooperative effect. Russ. J. Gen. Chem. 77(10), 1742–1748 (2007)

    Article  CAS  Google Scholar 

  20. Perrin, D.D., Armarego, W.L.F., Perrin, D.R.: Purification of Laboratory Chemicals. Pergamon Press, Oxford (1980)

    Google Scholar 

  21. Abraham, M.H., McGowan, J.C.: The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography. Chromatographia 23(4), 243–246 (1987)

    Article  CAS  Google Scholar 

  22. Solomonov, B.N., Varfolomeev, M.A., Novikov, V.B., Klimovitskii, A.E.: New thermochemical parameter for describing solvent effects on ir stretching vibration frequencies communication 1. Assessment of van der waals interactions. Spectrochim. Acta A 64(2), 397–404 (2006)

    Article  Google Scholar 

  23. Solomonov, B.N., Varfolomeev, M.A., Novikov, V.B.: A new method for the determination of cooperative hydrogen bonding enthalpy of proton acceptors with associated species of alcohols. J. Phys. Org. Chem. 19(4), 263–268 (2006)

    Article  CAS  Google Scholar 

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Acknowledgements

The reported study was funded by RFBR, project number 19-33-60096.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, Universitetskii Prospect 26, Saint Petersburg, 198504, Russia

    Ilnaz T. Rakipov & Konstantin N. Semenov

  2. Pavlov First Saint Petersburg State Medical University, L’va Tolstogo Ulitsa 6–8, Saint Petersburg, 197022, Russia

    Konstantin N. Semenov

  3. Department of Physical Chemistry, Kazan Federal University, Kremlevskaya 18, Kazan, 420008, Russia

    Artem A. Petrov, Aydar A. Akhmadiyarov, Artashes A. Khachatrian, Alexander E. Klimovitskii & Boris N. Solomonov

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  1. Ilnaz T. Rakipov
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  2. Konstantin N. Semenov
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  3. Artem A. Petrov
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  4. Aydar A. Akhmadiyarov
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  5. Artashes A. Khachatrian
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  6. Alexander E. Klimovitskii
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  7. Boris N. Solomonov
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Correspondence to Ilnaz T. Rakipov.

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Rakipov, I.T., Semenov, K.N., Petrov, A.A. et al. FTIR Spectroscopy of Intermolecular Interactions of Ethers with Methanol: Cooperativity Effect. J Solution Chem 51, 1219–1228 (2022). https://doi.org/10.1007/s10953-022-01193-9

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  • DOI: https://doi.org/10.1007/s10953-022-01193-9

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