Open for submissionsPeer reviewed, fully open access, and a low article processing charge.Submit manuscript

Research ArticleOpen AccessGoogle Scholar indexed

Quantum Mechanical Studies on the Mode of Hydrogen Bonding, Stability and Molecular Conformations of Phenol-Water Complexes

,
,
,
  1. 1 Department of Applied Sciences, Gauhati University, Guwahati, India
Computational Chemistry·Volume 07, Issue 3·Pages 59–71·Published 3 July 2019·DOI10.4236/cc.2019.73005
Download PDF

Abstract

It is experimentally well established that the phenolic systems such as phenol and diphenols undergo strong hydrogen bonding interaction with water molecule. But, the possible mode hydrogen bonding in phenol-water systems may be of different types. Although, the experimental methods are not always well enough to give the proper hydrogen bonding conformations in the phenol-water complexes. The hydrogen bonding ability in phenol-water systems can directly be influenced by changing the interacting sites in the given molecular systems, which could be investigated by theoretical studies. Generally, in phenol-water system, the hydrogen bonding is taking place through −OH group of phenol with water molecule, and this kind of interactions between phenol-water and diphenol-water complexes have been extensively investigated in electronic ground state by Quantum Mechanical MP4 calculations. It is also very important to study the stability of different phenol-water complexes and to find out the proper phenol-water complexes with minimized interaction energy. This study will also be helpful for understanding the effect of hydrogen bonding interaction in a better way on other aromatic systems.

KeywordsPhenolDiphenolMP4 MethodHydrogen Bonding
  1. Salonen, L.M., Ellermann, M. and Diederich, F. (2011) Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures. Angewandte Chemie International Edition, 50, 4808-4842. https://doi.org/10.1002/anie.201007560
  2. Schottel, B.L., Chifotides, H.T. and Dunbar, K.R. (2008) Anion-pi Interactions. Chemical Society Review, 37, 68-83. https://doi.org/10.1039/B614208G
  3. Ma, J.C. and Dougherty, D.A. (1997) The Cation-pi Interaction. Chemical Review, 97, 1303-1324. https://doi.org/10.1021/cr9603744
  4. Hunter, C.A., Lawson, K.R., Perkin, J. and Urch, C.J. (2001) Aromatic Interactions. Journal of the American Chemical Society, Perkin Transactions, 2, 651-669. https://doi.org/10.1039/b008495f
  5. Grabowski, S.J. (2011) What Is the Covalency of Hydrogen Bonding. Chemical Review, 111, 2597-2625. https://doi.org/10.1021/cr800346f
  6. Kone, M., Illien, B., Laurence, C. and Graton, J. (2011) Can Quantum-Mechanical Calculations Yield Reasonable Estimates of Hydrogen Bonding Acceptor Strength? The Case of Hydrogen-Bonded Complexes of Methanol. Journal of Physical Chemistry A, 115, 13975-13985. https://doi.org/10.1021/jp209200w
  7. Albrecht, L. and Boyd, R.J. (2012) Visualizing Internal Stabilization in Weakly Bound Systems Using Atomic Energies: Hydrogen Bonding in Small Water Clusters. Journal of Physical Chemistry A, 116, 3946-3951. https://doi.org/10.1021/jp301006g
  8. Lodish, H., Berk, A., Zipursky, S.L., Matsudaira, P., Baltimore, D. and Darnel, J. (2000) Molecular Cell Biology. 4th Edition, W. H. Freeman, New York.
  9. Biswal, H.S., Chakraborty, S. and Wategaonkar, S. (2008) Experimental Evidence of O-H-S Hydrogen Bonding in Supersonic Jet. Journal of Chemical Physics, 129, Article ID: 184311. https://doi.org/10.1063/1.3012569
  10. Biswal, H.S., Shirhatti, P.R. and Wategaonkar, S. (2010) O-H⋅⋅⋅O versus O-H⋅⋅⋅S Hydrogen Bonding. 2. Alcohols and Thiols as Hydrogen Bond Acceptors. Journal of Physical Chemistry A, 114, 6944-6955. https://doi.org/10.1021/jp102346n
  11. Xu, L.H., Liu, Q., Suenram, R.D., Lovas, F.J., Walker, A.R.H., Jensen, J.O. and Samuels, A.C. (2004) Rotational Spectra, Conformational Structures, and Dipole Moments of Thiodiglycol by Jet-Cooled FTMW and Ab Initio Calculations. Journal of Moleculer Spectroscopy, 228, 243-250. https://doi.org/10.1016/j.jms.2004.04.004
  12. Pal, D. and Chakrabarti, P. (1998) Different Types of Interactions Involving Cysteine Sulfhydryl Group in Proteins. Journal of Biomolecular Structure and Dynamics, 15, 1059-1072. https://doi.org/10.1080/07391102.1998.10509001
  13. Zauhar, R.J., Colbert, C.L., Morgan, R.S. and Welsh, W.J. (2000) Evidence for a Strong Sulfur-Aromatic Interaction Derived from Crystallographic Data. Biopolymers, 53, 233-248. https://doi.org/10.1002/(SICI)1097-0282(200003)53:3<233::AID-BIP3>3.0.CO;2-4
  14. Krepps, M.K., Parkin, S. and Atwood, D.A. (2001) Hydrogen Bonding with Sulfur. Crystal Growth Design, 1, 291-297. https://doi.org/10.1021/cg015505v
  15. Francuski, B.M., Novakovic, S.B. and Bogdanovic, G.A. (2011) Electronic Features and Hydrogen Bonding Capacity of the Sulfur Acceptor in Thioureido-Based Compounds. Experimental Charge Density Study of 4-methyl-3-thiosemicarbazide. CrystEngComm, 13, 3580-3591. https://doi.org/10.1039/c0ce00760a
  16. Howard, D.L. and Kjaergaard, H.G. (2008) Hydrogen Bonding to Divalent Sulphur. Physical Chemistry Chemical Physics, 10, 4113-4118. https://doi.org/10.1039/b806165c
  17. Novakovic, S.B., Fraisse, B., Bogdanovic, G.A. and Spasojevic-De Bire, A. (2007) Experimental Charge Density Evidence for the Existence of High Polarizability of the Electron Density of the Free Electron Pairs on the Sulfur Atom of the Thioureido Group, NH-C(S)-NH2, Induced by N-H⋅⋅⋅S and C-H⋅⋅⋅S Interactions. Crystal Growth Design, 7, 191-195. https://doi.org/10.1021/cg060497+
  18. Levitt, M. and Perutz, M.F. (1988) Aromatic Rings Act as Hydrogen Bond Acceptors. Journal of Molecular Biology, 201, 751-754. https://doi.org/10.1016/0022-2836(88)90471-8
  19. Brinkley, R.L. and Gupta, R.B (2004) Hydrogen Bonding with Aromatic Ring. American Institute of Chemical Engineers, 47, 948-953. https://doi.org/10.1002/aic.690470417
  20. Schamnad, S. and Chakraborty, S. (2015) Substituent Effect in O-H⋅⋅⋅Se Hydrogen Bond—Density Functional Theory Study of Para-Substituted Phenol-SeH2 Complexes. Chemical Physics Letters, 622, 28-33. https://doi.org/10.1016/j.cplett.2015.01.012
  21. Harada, T., Yoshida, H., Ohno, K., Matsuura, H., Zhang, J., Iwaoka, M. and Tomod, S. (2001) Implications of Intramolecular OH⋅⋅⋅Se Hydrogen Bonding and CH⋅⋅⋅O Interaction in the Conformational Stabilization of 2-(Methylseleno)ethanol Studied by Vibrational Spectroscopy and Density Functional Theory. Journal of Physical Chemistry A, 105, 4517-4523. https://doi.org/10.1021/jp003990j
  22. Nepal, B. and Scheiner, S. (2014) Effect of Ionic Charge on the CH⋅⋅⋅π Hydrogen Bond. Journal of Physical Chemistry A, 118, 9575-9587. https://doi.org/10.1021/jp5070598
  23. Xue, B., et al. (2014) Luminol: Extended Hydrogen Bond Network in Water Solution. Computational and Theoretical Chemistry, 1028, 81-86. https://doi.org/10.1016/j.comptc.2013.11.022
  24. Furutaka, S. and Ikawa, S. (1998) Hydrogen Bonding of Water with Aromatic Hydrocarbons at High Temperature and Pressure. The Journal of Chemical Physics, 108, 5159-5160. https://doi.org/10.1063/1.475953
  25. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, T., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewaki, V.G., Ortiz, J.V., Foresmann, J.B., Ciolowski, J., Stefanov, B.B., Namayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, W., Wong, M.W., Andres, J.L., Replogle, E.S., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., Defrees, D.J., Baker, J., Stewart, J.P., Head-Gordon, M., Gonzalez, C. and Pople, J.A. (2009) Gaussian 09. Gaussian Inc., Pittsburgh.
  26. Josefin, E.U., Mikael, K., Dick, S. and Bjorn, A. (2006) Water as a Hydrogen Bonding Bridge between a Phenol and Imidazole. A Simple Model for Water Binding in Enzymes. Biochimica et Biophysica Acta, 1757, 1592-1596. https://doi.org/10.1016/j.bbabio.2006.08.005