Abstract
The results of numerical modeling of p-hydroxybenzoic acid, methylparaben, and propylparaben solutions in methanol-modified supercritical carbon dioxide were presented. The composition, structure, and formation energy of the solute–cosolvent hydrogen-bonded complexes were determined. The duration of the existence of hydrogen bonds via individual paraben atoms was evaluated based on the data of Car–Parrinello ab initio molecular dynamics simulation, and the potential of mean force of interaction with methanol was calculated taking into account the medium. It was shown that, despite the presence of several potential centers of specific interaction, p-hydroxybenzoic acid and its derivatives form hydrogen bonds mainly via carboxyl and hydroxyl protons, respectively.
Similar content being viewed by others
REFERENCES
M. R. Lee, C. Y. Lin, Z. G. Li, and T. F. Tsai, J. Chromatogr. A 1120, 244 (2006).
M. Asghari-Khiavi and Y. Yamini, J. Chem. Eng. Data 48, 61 (2003).
I. M. Gil’mutdinov, I. I. Gil’mutdinov, I. V. Kuznetsova, and A. N. Sabirzyanov, Theor. Found. Chem. Eng. 50, 15 (2016).
K. W. Cheng, M. Tang, and Y. P. Chen, Fluid Phase Equilib. 201, 79 (2002).
J. S. Jin, Z. T. Zhang, Q. S. Li, et al., J. Chem. Eng. Data 50, 801 (2005).
F. P. Lucien and N. R. Foster, Ind. Eng. Chem. Res. 35, 4686 (1996).
M. R. Junior, A. V. Leite, and N. R. Dragano, Open Chem. Eng. J. 4, 51 (2010).
F. Ingrosso and M. F. Ruiz-López, ChemPhysChem 18, 2560 (2017).
J. Jin, C. Zhong, Z. Zhang, and Y. Li, Fluid Phase Equilib. 226, 9 (2004).
K. E. Anderson and J. I. Siepmann, J. Phys. Chem. B 112, 11374 (2008).
P. M. Agrawal, B. M. Rice, D. C. Sorescu, and D. L. Thompson, Fluid Phase Equilib. 166, 1 (1999).
A. I. Frolov and M. G. Kiselev, J. Phys. Chem. B 118, 11769 (2014).
D. L. Gurina, M. L. Antipova, E. G. Odintsova, and V. E. Petrenko, J. Supercrit. Fluids 120, 59 (2017).
D. L. Gurina, M. L. Antipova, E. G. Odintsova, and V. E. Petrenko, J. Supercrit. Fluids 126, 47 (2017).
M. J. Abraham, D. van der Spoel, E. Lindahl, and B. Hess (GROMACS Development Team), GROMACS User Manual, Version 5.0.7 (2015). www.gromacs.org.
W. L. Jorgensen, D. S. Maxwell, and J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225 (1996).
A. Zhu, X. Zhang, L. I. U. Qinglin, and Q. Zhang, Chin. J. Chem. Eng. 17, 268 (2009).
M. P. Allen and D. J. Tildesley, Computer Simulations of Liquids (Clarendon, Oxford, 1987).
S. Nose, Mol. Phys. 52, 255 (1984).
W. G. Hoover, Phys. Rev. A 31, 1695 (1985).
T. Darden, D. York, and L. Pedersen, J. Chem. Phys. 98, 10089 (1993).
U. Essmann, L. Perera, M. L. Berkowitz, et al., J. Chem. Phys. 103, 8577 (1995).
B. Hess, H. Bekker, H. J. C. Berendsen, and J. G. E. M. Fraaije, J. Comput. Chem. 18, 1463 (1997).
W. Humphrey, A. Dalke, and K. Schulten, J. Mol. Graphics 14, 33 (1996).
J. Hutter, A. Alavi, T. Deutch, et al., CPMD Program (MPI Festkörperforschung, Stuttgart, 1997–2001; IBM Corp., 1990–2008).
A. D. Becke, Phys. Rev. A 38, 3098 (1988).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
D. Vanderbilt, Phys. Rev. B 41, 7892 (1990).
D. L. Gurina, M. L. Antipova, and V. E. Petrenko, Russ. J. Phys. Chem. A 87, 1662 (2013).
J. Wang, Z. Wu, and F. Zhao, J. Supercrit. Fluids 58, 272 (2011).
ACKNOWLEDGMENTS
This study was financially supported by the Russian Foundation for Basic Research (project no. 16-33-60060).
We are grateful to the Joint Supercomputer Center, Russian Academy of Sciences (Moscow), for providing us with the resources on the MVS-100K cluster.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by L. Smolina
Rights and permissions
About this article
Cite this article
Gurina, D.L., Antipova, M.L., Odintsova, E.G. et al. Hydrogen-Bonded Complexes of p-Hydrobenzoic Acid and Its Derivatives with a Polar Cosolvent in Supercritical Carbon Dioxide. Russ. J. Phys. Chem. 93, 865–872 (2019). https://doi.org/10.1134/S0036024419050121
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024419050121