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Electron Density, Interaction Energy and Hydrogen-Bond Radius of C–H...O Interaction


Affiliations
1 Department of Physics, Amrit Campus, Tribhuvan University, Thamel, Kathmandu, Nepal
 

Atoms in theoretical analysis of molecules was used to study C–H...O interaction taking five different molecules with the same acceptor, O of water. The relation between electron density at hydrogen-bond critical point and interaction energy has been studied and hydrogen-bond radii were derived. Although a linear relationship was obtained like other intermolecular interactions, the value of linear parameters was found to be different when a similar type of interaction was compared suggesting that the parameters depend on the type of acceptor and donor and not the type of interaction. The H-bond radii for this type of interaction were found to have significant variance.

Keywords

Electron Density, Hydrogen-Bond Radius, Interaction Energy, Linear Parameters.
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  • Sutor, D. J., The C–H...O hydrogen bond in crystals. Nature, 1962, 195, 68–69.

  • Allen, F. H. et al., The Cambridge crystallographic data centre: computer-based search, retrieval, analysis and display of information. Acta Crystallogr., Sect. B, 1979, 835, 2331–2339.

  • Taylor, R. and Kennard, O., Crystallographic evidence for the existence of C–H...O, C–H...N and C–H...Cl hydrogen bonds. J. Am. Chem. Soc., 1982, 104, 5063–5070.

  • Takahashi, O. et al., Relevance of weak hydrogen bonds in the conformation of organic compounds and bioconjugates: evidence from recent experimental data and high-level ab initio MO calculations. Chem. Rev., 2010, 110, 6049–6076.

  • Desiraju, G. R. and Steiner, T., The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, UK, 1999.

  • Arunan, E. et al., Defining the hydrogen bond: an account (IUPAC technical report). J. Pure Appl. Chem., 2011, 83, 1619–1636.

  • Bader, R. F. W., Atoms in Molecules – A Quantum Theory, Oxford University Press, Oxford, UK, 1990.

  • Bader, R. F. W., A quantum theory of molecular structure and its applications. Chem. Rev., 1991, 91, 893–928.

  • Koch, U. and Popelier, P. L. A., Characterization of C–H–O hydrogen bonds on the basis of the charge density. J. Phys. Chem., 1995, 99, 9747–9754.

  • Lakshmi, B., Samuelson, A. G., Jovan Jose, K. V. and Gadre, S. R., Is there a hydrogen bond radius? Evidence from microwave spectroscopy, neutron scattering and X-ray diffraction results. New J. Chem., 2005, 29, 371–377.

  • Raghavendra, B., Mandal, P. K. and Arunan, E., Ab initio and AIM theoretical analysis of hydrogen-bond radius of HD (D = F, Cl, Br, CN, HO, HS and CCH) donors and some acceptors. Phys. Chem. Chem. Phys., 2006, 8, 5276.

  • Klein, R. A., Electron density topological analysis of hydrogen bonding in glucopyranose and hydrated glucopyranose. J. Am. Chem. Soc., 2002, 124, 13931–13937.

  • Klein, R. A., Modified van der Waals atomic radii for hydrogen bonding based on electron density topology. Chem. Phys. Lett., 2006, 425, 128–133.

  • Duchovic, R. J., Hase, W. L., Schlegel, H. B., Frisch, M. J. and Raghavchari, K., Ab initio potential energy curve for CH bond dissociation in methane. Chem. Phys. Lett., 1982, 89, 120–125.

  • McGivern, W. S., Derecskei-Kovacs, A., North, S. W. and Franscio, J. S., Computationally efficient methodology to calculate C−H and C−X (X = F, Cl, and Br) bond dissociation energies in haloalkanes. J. Phys. Chem. A, 2000, 104, 436–442.

  • Goebbert, D. J., Velarde, L., Khuseynov, D. and Sanov, A., C–H bond dissociation energy of malononitrile. J. Phys. Chem. Lett., 2009, 1, 792–795.

  • Barckholtz, C., Barckholtz, T. A. and Hadad, C. M., C–H and N–H bond dissociation energies of small aromatic hydrocarbons. J. Am. Chem. Soc., 1999, 121, 491–500.

  • http://www.chem.wisc.edu/areas/reich/pkatable/index.htm (accessed 28 March 2017).

  • Raghavendra, B. and Arunan, E., Hydrogen bonding with a hydrogen bond: The methane–water complex and the penta-coordinate carbon. Chem. Phys. Lett., 2008, 467, 37–40.

  • Rosenberg, R. E., Does fluoromethane form a hydrogen bond with water? J. Phys. Chem. A, 2012, 116, 10842–10849.

  • Frisch, M. J. et al., GAUSSIAN 03, revision E.01; Gaussian, Inc., Wallingford, CT, USA, 2004.

  • Biegler-Konig, F., Schonbohm, J., Derdau, R., Bayles, D. and Bader, R. F. W., AIM 2000, version 1; Buro fur Innovative Software, Bielefeld, Germany, 2000.

  • Boys, S. B. and Bernardi, F., The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys., 1970, 19, 553–566.

  • Raghavendra, B. and Arunan, E., Unpaired and sigma bond electrons as H, Cl, and Li bond acceptors: An anomalous one-electron blue-shifting chlorine bond. J. Phys. Chem. A, 2007, 111, 9699–9706.

  • Shahi, A. and Arunan, E., Hydrogen bonding, halogen bonding and lithium bonding: an atoms in molecules and natural bond orbital perspective towards conservation of total bond order, interand intra-molecular bonding. Phys. Chem. Chem. Phys., 2014, 16, 22935–22952.

  • Parajuli, R. and Arunan, E., Comprehensive investigations on DNA...A (D = H/F) complexes show why ‘sodium bonding’ is not commonly observed. Chem. Phys. Lett., 2013 568–569, 63–69.

  • Karan, N. K. and Arunan, E., Chlorine bond distances in ClF and Cl2 complexes. J. Mol. Struct., 2004, 688, 203–205.


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  • Electron Density, Interaction Energy and Hydrogen-Bond Radius of C–H...O Interaction

Abstract Views: 260  |  PDF Views: 75

Authors

R. Parajuli
Department of Physics, Amrit Campus, Tribhuvan University, Thamel, Kathmandu, Nepal

Abstract


Atoms in theoretical analysis of molecules was used to study C–H...O interaction taking five different molecules with the same acceptor, O of water. The relation between electron density at hydrogen-bond critical point and interaction energy has been studied and hydrogen-bond radii were derived. Although a linear relationship was obtained like other intermolecular interactions, the value of linear parameters was found to be different when a similar type of interaction was compared suggesting that the parameters depend on the type of acceptor and donor and not the type of interaction. The H-bond radii for this type of interaction were found to have significant variance.

Keywords


Electron Density, Hydrogen-Bond Radius, Interaction Energy, Linear Parameters.

References





DOI: https://doi.org/10.18520/cs%2Fv114%2Fi06%2F1295-1298