Abstract
Quantum chemical calculations were performed at different levels of theory (SCF, DFT, MP2, and CCSD(T)) to determine the geometry and electronic structure of the HOH···CH4 complex formed by water and methane molecules, in which water is a proton donor and methane carbon (sp 3) is an acceptor. The charge distribution on the atoms of the complex was analyzed by the CHelpG method and Hirshfeld population analysis; both methods revealed the transfer of electron charge from methane to water. According to the natural bond orbital (NBO) analysis data, the charge transfer upon complexation is caused by the interaction between the σ orbital of the axial С–H bond of methane directed along the line of the O–H···C hydrogen bridge and the antibonding σ* orbital of the О–H bond of the water molecule. Topological analysis of electron density in the HOH···CH4 complex by the AIM method showed that the parameters of the critical point of the bond between hydrogen and acceptor (carbon atom) for the O–H···C interaction are typical for Н-bonded systems (the magnitude of electron density at the critical point of the bond, the sign and value of the Laplacian). It was concluded that the intermolecular interaction in the complex can be defined as an Н bond of O–H···σ(С–H) type, whose energy was found to be 0.9 kcal/mol in MP2/aug-cc-pVQZ calculations including the basis set superposition error (BSSE).
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A. Bhattacherjee, Y. Matsuda, A. Fujii, and S. Wategaonkar, ChemPhysChem 14, 905 (2013).
K. Grzechnik, K. Rutkowski, and Z. Mielke, J. Mol. Struct. 1009, 96 (2012).
H. S. Biswal and S. Wategaonkar, J. Phys. Chem. A 113, 12774 (2009).
G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology (Oxford, New York, 1999).
M. Nishio, in Encyclopedia of Supramolecular Chemistry, Ed. by J. L. Atwood and J. W. Steed (Marcel Dekker, New York, 2004).
E. Arunan, G. R. Desiraju, R. A. Klein, et al., Pure Appl. Chem. 83, 1637 (2011).
S. Glasstone, Trans. Faraday Soc. 33, 200 (1937).
J. F. J. Dippy, Chem. Rev. 25, 151 (1939).
D. J. Sutor, Nature 195, 68 (1962).
D. J. Sutor, J. Chem. Soc., 1105 (1963).
M. Oki and H. Iwamura, J. Am. Chem. Soc. 89, 576 (1967).
Z. Yoshida and E. Osawa, J. Am. Chem. Soc. 87, 1467 (1965).
M. F. Perutz, Phil. Trans. R. Soc. A 345, 105 (1993).
D. A. Rodham, S. Suzuki, R. D. Suenram, et al., Nature 362, 735 (1993).
E. S. Stoyanov, S. P. Hoffmann, K.-C. Kim, et al., J. Am. Chem. Soc. 127, 7664 (2005).
M. Saggu, N. M. Levinson, and S. G. Boxer, J. Am. Chem. Soc. 133, 17414 (2011).
M. Saggu, N. M. Levinson, and S. G. Boxer, J. Am. Chem. Soc. 134, 18986 (2012).
J. E. del Bene, Chem. Phys. Lett. 24, 203 (1974).
W. G. Read and W. H. Flygare, J. Chem. Phys. 76, 2238 (1982).
J. A. Shea and W. H. Flygare, J. Chem. Phys. 76, 4857 (1982).
B. G. de Oliveira, Phys. Chem. Chem. Phys. 15, 37 (2013).
D. Quiñonero, A. Frontera, D. Escudero, et al., Theor. Chem. Acc. 120, 385 (2008).
D. Quiñonero, C. Estarellas, A. Frontera, and P. M. Deyá, Chem. Phys. Lett. 508, 144 (2011).
A. Ebrahimi, M. Habibi, and H. R. Masoodi, Chem. Phys. Lett. 478, 120 (2009).
S. M. Malathy Sony and M. N. Ponnuswamy, Cryst. Growth Des. 6, 736 (2006).
K. E. Riley, M. Pitonák, J. Cerný, and P. Hobza, J. Chem. Theory Comput. 6, 66 (2010).
R. Parthasarathi, V. Subramanian, N. Sathyamurthy, and J. Leszczynski, J. Phys. Chem. A 111, 2 (2007).
D-l. Cao, X-q. Feng, et al., J. Mol. Struct.: THEOCHEM 849, 76 (2008).
F-d. Ren, D-l. Cao, W-l. Wang, et al., Chem. Phys. Lett. 455, 32 (2008).
J. P. Foster and F. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980).
A. E. Reed, F. Weinhold, L. A. Curtiss, and D. J. Pochatko, J. Chem. Phys. 84, 5687 (1986).
A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev. 88, 899 (1988).
J. Urban, S. Roszak, and J. Leszczynski, Chem. Phys. Lett. 346, 512 (2001).
J. J. Szymczak, S. J. Grabowski, S. Roszak, and J. Leszczynski, Chem. Phys. Lett. 393, 81 (2004).
S. J. Grabowski, W. A. Sokalski, and J. Leszczynski, J. Phys. Chem. A 108, 5823 (2004).
S. J. Grabowski, W. A. Sokalski, and J. Leszczynski, Chem. Phys. Lett. 432, 33 (2006).
R. F. W. Bader, Chem. Rev. 91, 893 (1991).
R. F. W. Bader, Atoms in Molecules, a Quantum Theory (Clarendon, Oxford, 1993).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, et al., Gaussian 09, Revision D.01 (Gaussian Inc., Wallingford CT, 2013).
R. A. Kendall, T. H. Dunning, and R. J. Harrison, J. Chem. Phys. 96, 6796 (1992).
C. Moller and M. S. Plesset, Phys. Rev. 46, 618 (1934).
J. A. Pople, R. Seeger, and R. Krishnan, Int. J. Quantum Chem. Symp. 11, 149 (1977).
G. D. Purvis and R. J. Bartlett, J. Chem. Phys. 76, 1910 (1982).
G. E. Scuseria and H. F. Schaefer, J. Chem. Phys. 90, 3700 (1989).
Y. Zhao and D. G. Truhlar, Theor. Chem. Acc. 120, 215 (2008).
M. A. Vincent and I. H. Hillier, Phys. Chem. Chem. Phys. 13, 4388 (2011).
M. J. Biller and S. Mecozzi, Mol. Phys. 110, 377 (2012).
M. Majumder, B. K. Mishra, and N. Sathyamurthy, Chem. Phys. 557, 59 (2013).
S. Karthikeyan, V. Ramanathan, and B. K. Mishra, J. Phys. Chem. A 117, 6687 (2013).
S. F. Boys and F. Bernardi, Mol. Phys. 19, 553 (1970).
T. Lu and F. Chen, J. Comput. Chem. 33, 580 (2012).
C. M. Breneman and K. B. Wiberg, J. Comput. Chem. 11, 361 (1990).
F. Martin and H. Zipse, J. Comput. Chem. 26, 97 (2005).
F. L. Hirshfeld, Theor. Chim. Acta (Berlin) 44, 129 (1977).
Ya. Gu, T. Kar, and S. Scheiner, J. Am. Chem. Soc. 121, 9411 (1999).
S. Scheiner, S. J. Grabowski, and T. Kar, J. Phys. Chem. A 105, 10607 (2001).
P. Hobza and Z. Havlas, Chem. Rev. 100, 4253 (2000).
S. Scheiner, Hydrogen Bonding: A Theoretical Perspective (Oxford Univ. Press, New York, 1997).
J. Mathieu and R. Panico, Reaction Mechanisms of Organic Chemistry (Hermann, Paris, 1972).
G. Praveena and P. Kolandaivel, J. Mol. Struct. 828, 154 (2007).
A. N. Isaev, Russ. J. Phys. Chem. A 90, 601 (2016).
U. Koch and P. L. A. Popelier, J. Phys. Chem. 99, 9747 (1995).
P. L. A. Popelier, J. Phys. Chem. A 102, 1873 (1998).
O. Mo, M. Yánez, and J. Elguero, J. Mol. Struct.: THEOCHEM 314, 73 (1994).
E. Espinosa, E. Molins, and C. Lecomte, Chem. Phys. Lett. 285, 170 (1998).
E. Cubero, M. Orozco, P. Hobza, and F. J. Luque, J. Phys. Chem. A 103, 6394 (1999).
S. J. Grabowski and P. Lipkowski, J. Phys. Chem. A 115, 4765 (2011).
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Original Russian Text © A.N. Isaev, 2016, published in Zhurnal Fizicheskoi Khimii, 2016, Vol. 90, No. 10, pp. 1497–1504.
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Isaev, A.N. O–H···C hydrogen bond in the methane–water complex. Russ. J. Phys. Chem. 90, 1978–1985 (2016). https://doi.org/10.1134/S0036024416100150
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DOI: https://doi.org/10.1134/S0036024416100150