Theoretical Studies of Hydrogen Bond Interactions in 4-Substituted Benzoic Acids Dimers
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Two conformations of benzoic acid derivatives (NH_2, OH, H, F, Cl, CN, NO, NO_2) have been investigated at MP2, DFT and HF level using the 6-311++G(d,p) basis set. It was found that the cis isomers are more stable. Hydrogen bonding formation of benzoic acids has been estimated from stabilization energies. The calculated hydrogen-bonding energies of dimers showed a cooperative interaction in the cyclic ones. It was found that an electron-releasing group (ERG) into the phenyl rings resulted in the formation of more stable hydrogen bonding. Red shift of O–H bond was found from -565.3 to -589.3for dimers. The natural bond orbital (NBO) analysis was applied to characterize nature of the interaction.
Abstract
Two conformations of benzoic acid derivatives (NH_2, OH, H, F, Cl, CN, NO, NO_2) have been investigated at MP2, DFT and HF level using the 6-311++G(d,p) basis set. It was found that the cis isomers are more stable. Hydrogen bonding formation of benzoic acids has been estimated from stabilization energies. The calculated hydrogen-bonding energies of dimers showed a cooperative interaction in the cyclic ones. It was found that an electron-releasing group (ERG) into the phenyl rings resulted in the formation of more stable hydrogen bonding. Red shift of O–H bond was found from -565.3 to -589.3for dimers. The natural bond orbital (NBO) analysis was applied to characterize nature of the interaction.
참고문헌 (40)
- Scheiner, S., "Hydrogen Bonding" (1997), Oxford University Press
- Jeffery, G. A., "Introduction to Hydrogen Bonding" (1997), Oxford University Press
- Hobza, P., , Chem. Rev, 100, pp.4253~ (2000)
- Genin, F., , Phys. Chem. Chem. Phys, 3, pp.932~ (2001)
- Emmeluth, C., , Phys. Chem. Chem. Phys, 5, pp.3094~ (2003)
- Goldman, M. A., , J. Phys. Chem, 77, pp.2295~ (1973)
- Lumbroso-Bader, N., , J. Magnetic Resonance, 17, pp.386~ (1969)
- Yoshida, N., , J. Phys. Chem, 86, pp.1785~ (1982)
- Stricter, F. J., , Acta Crysrallogr, 15, pp.1233~ (1962)
- Kanters, J. A., , Kroon, J. Acta Crysrallogr, 828, pp.1946~ (1972)
- Albinati, A., , Acta Crystallogr., Sect, B: Struct. Crystallogr. Crystal Chem, 34, pp.2188~ (1978)
- Van Eijck, B. P, , Journal of Molecular Structure, 44, pp.1~ (1978)
- Van Eijck, B. P., , Journal of Molecular Structure, 11, pp.67~ (1972)
- Taylor, M. D., , J. Am. Chem. Soc, 73, pp.315~ (1951)
- Karle, J., , J. Am. Chem. Soc, 66, pp.574~ (1944)
- Frurip, D. J., , J. Am. Chem. Soc, 102, pp.2610~ (1980)
- Aquino, A. J. A., , J. Phys. Chem, 106, pp.1862~ (2002)
- Turi, L., , J. Phys. Chem, 100, pp.11285~ (1996)
- Wolfs, I., , J. Mol. Struct. (Theochem.), 81, pp.360~ (1996)
- Lewandowski, H., , J. Vibrational Spectroscopy, 39, pp.15~ (2005)
- Chocholousova, J., , J. Phys. Chem, 107, pp.3086~ (2003)
- Turi, L., , J. Phys. Chem., 97, pp.12197~ (1993)
- Grabowski, S. J., "Hydrogen Bonding-New Insights" (2006), Spriger
- Jeffrey, G. A., "Hydrogen bonding in biological systems" (1991), Spriger-Verlag
- Hadzi, D., "Theoretical Treatments of Hydrogen Bonding" (1997), John Wiley & Sons
- Steiner, T., , Angew. Chem. Int. Ed, 41, pp.48~ (2002)
- Minatchy, S., , Ind. J. Chem, 37, pp.1066~ (1998)
- Mani, P., , 박사, pp.2004
- Hartree, R., , Proc. Camb. Philos. Soc, 24, pp.89~ (1927)
- Fock, V. Z., , Phys, 61, pp.126~ (1930)
- Slater, J. C., , Phys. Rev, 35, pp.120~ (1930)
- Møller, C., , Phys. Rev, 46, pp.618~ (1934)
- Parr, R. G., "Density-Functional Theory of Atoms and Molecules" (1994), Oxford University Press
- Lee, C., , Phys. Rev, 37, pp.785~ (1988)
- Becke, A. D., , J. Chem. Phys, 98, pp.1372~ (1993)
- Frisch, M. J., "GAUSSIAN 98, Revision A.11" (1998), Gaussian Inc
- Boys, S. F., , Mol. Phys, 19, pp.553~ (1970)
- Boys, S. F., , Reprinted in Mol Phys, 100, pp.65~ (2002)
- Glendening, E. D., "NBO Version 3.1", Theoretical Chemistry Institute University of Wisconsin
- Wysokin´ ski, R., , Journal of Molecular Structure, 791, pp.10~ (2006)