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http://dx.doi.org/10.5012/jkcs.2011.55.3.392

Theoretical Studies of Hydrogen Bond Interactions in 4-Substituted Benzoic Acids Dimers  

Beni, Alireza Salimi (Department of Chemistry, Faculty of Science, Yasouj University)
Chermahini, Alireza Najafi (Department of Chemistry, Faculty of Science, Yasouj University)
Sharghi, Hashem (Department of Chemistry, Faculty of Science, Shiraz University)
Publication Information
Journal of the Korean Chemical Society / v.55, no.3, 2011 , pp. 392-399 More about this Journal
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 -589.3 for dimers. The natural bond orbital (NBO) analysis was applied to characterize nature of the interaction.
Keywords
Hydrogen bonding; Benzoic acid; Substituted effect; NBO analysis; DFT; MP2; HF;
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  • Reference
1 Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.   DOI
2 Becke, A. D. J. Chem. Phys. 1993, 98, 1372.   DOI
3 Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules, Oxford University Press: New York, 1994.
4 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B 37, 785.
5 Frisch, M. J. et al., GAUSSIAN 98, Revision A.11, Gaussian Inc., Pittsburgh, PA, 1998.
6 Boys, S. F.; Bernadari, F. Mol. Phys. 1970, 19, 553.   DOI
7 Boys, S. F.; Bernardi, F. Reprinted in Mol Phys. 2002, 100, 65.   DOI
8 Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1 Theoretical Chemistry Institute University of Wisconsin: Madison.
9 Wysokinski, R.; Michalska, D.; Bienko, D.C.; Ilakiamani, S.; Sundaraganesan, N.; Ramalingam, K. Journal of Molecular Structure. 2006, 791, 70.   DOI
10 Taylor, M. D. J. Am. Chem. Soc. 1951, 73, 315.   DOI
11 Karle, J.; Brockway, L. O. J. Am. Chem. Soc. 1944, 66, 574.   DOI
12 Frurip, D. J.; Curtiss, L. A.; Blander, M. J. J. Am. Chem. Soc. 1980, 102, 2610.   DOI
13 Aquino, A. J. A.; Tunega, D.; Haberhauer, G.; Gerzabek, M. H. Lischka, H. J. Phys. Chem. 2002, 106, 1862.   DOI   ScienceOn
14 Turi, L. J. Phys. Chem. 1996, 100, 11285.   DOI
15 Wolfs, I.; Desseyn, H. O. J. Mol. Struct. (Theochem.) 1996, 81, 360.
16 Lewandowski, H.; Koglin, E.; Meier, R. J. Vibrational Spectroscopy 2005, 39, 15.   DOI
17 Chocholousova, J.; Vacek, J.; Hobza, P. J. Phys. Chem. 2003, 107, 3086.   DOI   ScienceOn
18 Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197.   DOI
19 Steiner, T. Angew. Chem. Int. Ed. 2002, 41, 48.   DOI
20 Grabowski, S. J. Hydrogen Bonding-New Insights; Spriger: 2006.
21 Mani, P. Ph. D.; Thesis Pondicherry University, 2004, p107.
22 Jeffrey, G. A.; Saenger, W. Hydrogen bonding in biological systems, Spriger-Verlag: Berlin, 1991.
23 Hadzi, D. Theoretical Treatments of Hydrogen Bonding; John Wiley & Sons: Chichester, New York, Weinheim, Brisbane, Singapore, Toronto, 1997.
24 Minatchy, S.; Mathew, N. Ind. J. Chem. 1998, 37B, 1066.
25 Hartree, R. Proc. Camb. Philos. Soc. 1927, 24, 89.
26 Fock, V. Z. Phys. 1930, 61, 126.   DOI
27 Slater, J. C. Phys. Rev. 1930, 35, 210.
28 Scheiner, S. Hydrogen Bonding; Oxford University Press: New York, 1997.
29 Jeffery, G. A. Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
30 Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253.   DOI
31 Genin, F.; Quiles, F.; Burneau A. Phys. Chem. Chem. Phys. 2001, 3, 932.   DOI   ScienceOn
32 Emmeluth, C.; Suhm, M. A. Phys. Chem. Chem. Phys. 2003, 5, 3094.   DOI   ScienceOn
33 Goldman, M. A.; Emerson, M. T. J. Phys. Chem. 1973, 77, 2295.   DOI
34 Kanters, J. A.; Kroon, J. Acta Crysrallogr. 1972, 828, 1946.
35 Lumbroso-Bader, N.; Coupry, C.; Baron, D.; Clague, D. H.; Govil, G. J. Magnetic Resonance. 1969, 17, 386.
36 Yoshida, N. J. Phys. Chem. 1982, 86, 1785.   DOI
37 Stricter, F. J.; Templeton, D. H.; Scheuerman, R. F.; Sass, R. L. Acta Crysrallogr. 1962, 15, 1233.   DOI
38 Albinati, A.; Rouse, K. D.; Thomas, M. W. Acta Crystallogr., Sect, B: Struct. Crystallogr. Crystal Chem. 1978, 34, 2188.   DOI
39 Van Eijck, B. P; Brandts, P., Maas, J. P. M. Journal of Molecular Structure. 1978, 44, 1.   DOI
40 Van Eijck, B. P.; Van Der Plaats G Van Rogn PH; Journal of Molecular Structure. 1972, 11, 67.   DOI