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http://dx.doi.org/10.5012/jkcs.2003.47.2.096

DFT Studies on Hydrogen Bonding in Water Complexes of Amino-substituted Pyridine  

Gab-Yong Lee (Department of Chemistry, Catholic Univeristy of Daegu)
Ok-Ju Kim (Department of Chemistry, Catholic Univeristy of Daegu)
Publication Information
Journal of the Korean Chemical Society / v.47, no.2, 2003 , pp. 96-103 More about this Journal
Abstract
Density Functional Theory(DFT) calculations are performed to estimate the hydrogen bonding interaction energies in pyridine-water and amino-substituted pyridine-water complexes. Some equilibrium properties are also obtained for these complexes at B3LYP/aug-cc-pVDZ level. It is shown that the amino substitution increases the proton affinity of pyridine and stabilizes the hydrogen bond. The degree of stabilization upon formation of the complex varies with the number and the position of the amino groups.
Keywords
Amino-Substituted Pyridine-Water Complex; Hydrogen Bond; DFT Calculation;
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1 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, H.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, Y.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, F.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Gaussian, Inc.; Pittsburgh PA, 1995.
2 Andon, R. J. L.; Cox, J. D. J. Chem. Soc. 1952, 4601.   DOI
3 Cox, J. D. J. Chem. Soc. 1952, 4606.   DOI
4 Abe, J.; Nakanishi, K.; Touhara, H. J. Chem. Thermodyn. 1978, 10, 483.   DOI   ScienceOn
5 Marczak, W.; Giera, E. J. Chem. Thermodyn. 1988, 30, 241   DOI
6 Garland, C. W.; Nishigaki, K. J. Chem. Phys. 1976, 65,5298.   DOI
7 Narayanan, T.; Prafulla, B. V.; Kumar, A.; Gopal, E. S. R. Ber. Bunsen-Ges. Phy. Chem. 1991, 95, 12.   DOI   ScienceOn
8 Kieninger, M.; Suhai, S. J. Comput. Chem. 1996, 117,1508.   DOI   ScienceOn
9 Lozynski, M.; Rusinska-Roszak, D. J, Phys. Chem. A1998, 102, 2899.   DOI   ScienceOn
10 Novoa, J. J.; Sosa, C. J. Phys. Chem. 1995, 99, 15837.   DOI   ScienceOn
11 Adamo, C,; Barone, V. In Recent Advances in Density Functional Methods; Chong, D. P., Ed.; World Scientific: Singapore, 1997: Part III.
12 Guo, H.; Sirois, S.; Proynov, E. I.; Salahub, D. R. In Theoretical Treatments of Hydrogen Bonding; Hadzi, D., Ed.; Wiley: Chichester, 1997.
13 Lozynski, M.; Rusiuska-Roszak, D.; Mack, H. G. J. Phys. Chem. A 1998, 102, 2899.   DOI   ScienceOn
14 Sorensen, G. O.; Mahler, L.; Rastrup-Andersen, N. J. Mol. Struct. 1974, 20, 119.   DOI   ScienceOn
15 Wang, J.; Johnson, B. G.; Boyd, R. J.; Eriksson, L. K.J. Phys. Chem. 1996, 100, 6317.   DOI   ScienceOn
16 Papai I.; Gabor, J. J. Phys. Chem. A 2000, 104, 2132.   DOI   ScienceOn
17 Reed. A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev.1988, 99, 899.   DOI   ScienceOn
18 Takahashi, H.; Mamola, K.; Plyler, E. K. J. Mol. Spectrosc.1966, 21, 217.   DOI
19 Schneider, G. Z. Phys. Chem. Neue Folge. 1963, 37, 333.   DOI   ScienceOn
20 Almasy, L.; Cser, L.; Jancso, G. Physica B, 2000, 276-278, 446.   DOI   ScienceOn
21 Jeffrey, G. A. An Introduction to Hydrogen Bonding;Oxford University Press; New York, 1997.
22 Scheiner, S. Hydrogen Bonding; Oxford University Press; New York, 1997.   DOI   ScienceOn
23 Halgren, T. A. J. Comput. Chem. 1996, 17, 520.   DOI   ScienceOn
24 Tsuzuki, S.; Uchimaru, T.; Matsumura, K.; Mikami, M.; Tanabe. K. J. Chem. Phys. 1999, 110, 11906.   DOI
25 Becke, A. D. J Chem. Phys. 1993, 98, 1372.   DOI
26 Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. A 1998, 102, 3782.   DOI   ScienceOn
27 Del Bene, J. E.; Person, W. B.; Szczepaniak, K. J. Phys. Chem. 1995, 99, 10705.   DOI   ScienceOn
28 Elstner, M.; Hobza, P.; Franenheim, T.; Suhai. S.; Kaxiras, E. J. Chem. Phys. 2001, 114, 5149.   DOI   ScienceOn
29 Chandra, A. K.; Nguyen, M. T.; Zeegers-Huyskens, T.J. Phys. Chem. A 1998, 102, 6010.   DOI
30 Mo, O.; Janez, M. J. Phys. Chem. A 1998, 102, 8174.   DOI   ScienceOn
31 Gu, J.; Leszczynski, J. J. Phys. Chem. A 1998, 103,2744.   DOI
32 Sahn, V., Density Functional Theory III., Springer: New York, 1996.   DOI   ScienceOn
33 Niu, H.; Alexander, D. Mackerell, Jr. J. Phys. Chem. A2002, 106, 7820.   DOI   ScienceOn
34 Kohn, W.; Sham, L. J Phys. Rev. 1965, A140, 1133.   DOI   ScienceOn
35 Atkins, P. W.; Friedman, R. S. Molecular Qunaturm Mechanics, Oxford Univ. Press; New York, 1997.
36 Ostlund, N. HyperChem, Autodesk, Inc., Sausalito, CA, 1993.   DOI   ScienceOn
37 Dewar, M. J. S.; Zoebish, E. J.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.   DOI   ScienceOn
38 Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.   DOI   ScienceOn
39 Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am, Chem. Soc. 1985, 108, 3902.
40 Kasende, O.; Zeegers-Huyskens, Th. Spectrosc. Lett.1980, 13, 493.   DOI   ScienceOn
41 Zoidis, E.; Yarwood, J.; Danten, Y.; Besnard, M.Mol. Phys. 1995, 85, 373.   DOI   ScienceOn
42 Zoidis, E.; Yarwood, J.; Danten, Y.; Besnard, M. Mol. Phys. 1995, 85, 385.   DOI   ScienceOn
43 Kim, K.; Jordan, K. D. J. Phys. Chem. 1994, 98, 10089.   DOI   ScienceOn
44 Samanta, U.; Chakrabarti, P.; Chandrasekhar, J. J. Phys. Chem. A 1998, 102, 8964.   DOI
45 Del Bene, J. E. J. Am. Chem. Soc. 1975, 97, 5330.   DOI
46 Alagona, G.; Ghio, C.; Nagy, P. J. Mol. Struct. (THEOCHEM).1989, 187, 219.   DOI   ScienceOn
47 Ahn, D. S.; Park, S. W.; Lee, S.; Kim, B. J. Phys. Chem. A. 2003, 107, 131.   DOI   ScienceOn