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http://dx.doi.org/10.5012/jkcs.2007.51.1.007

DFT Studies on the Proton Affinities of Oxazole  

Lee, Hyun-Mee (Department of Chemistry, Yeungnam University)
Lee, Gab-Yong (Department of Life Chemistry, Catholic University of Daegu)
Publication Information
Journal of the Korean Chemical Society / v.51, no.1, 2007 , pp. 7-13 More about this Journal
Abstract
The oxazole plays an important role in the binding of lexitropsin to the guanine-cytosine base pair from minor groove of DNA. The geometry optimization is performed with DFT calculations for the two possible conformations of the protonated oxazole. The proton affinities are calculated at B3LYP level of theory with 6-31G* basis set for the optimized geometry. It is found that the proton affinites of the conformations in which the oxazole nitrogen is the protonation center are greater than that of the conformations in which the oxazole oxygen is the protonation center. This result is in good agreement with molecular electrostatic potential (MEP) contour map. The proton affinities are also studied for various substituted oxazoles with the electron-donating and -withdrawing groups to estimate substitutent effect on the proton affinity at the hydrogen bonding site of the oxazoles. it is shown that the electron-donating substituents increase the proton affinity of oxazole, while the electron-withdrawing substituents decrease it.
Keywords
Oxazole; Proton affinity; Substituent effect; DFT;
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1 Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5. 129   DOI
2 Connolly, M. L.; Olson, G. A. J. Comput. Chem. 1985, 6, 1   DOI
3 Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650   DOI
4 Hout, Jr., R. F.; Pietro, W. J.; Hehre, W. J. A Pictorial Approach to Molecular Structure and Reactivity New York, U.S.A., 1984
5 Kumar, S.; Jaseja, M.; Zimmermann, J.; Yadagiri, B.; Pon, T. R.; Sapse, A-M.; Lown, J. W. J. Biomol. Struct. Dyn. 1990, 8, 99
6 Lee, H. M.; Lee, G. Y. J. Kor. Chem. Soc. 1994, 38, 21
7 Lee, H. M.; Lee, S. E.; Chang, M. S.; Park, B. K.; Lee, G. Y. J. Kor. Chem. Soc. 1995, 39, 493
8 Lee, G. Y.; Lee, H. M. J. Kor. Chem. Soc., 1998, 42, 1
9 Pindur, U.; Fischer, G. Curr. Med. Chem., 1996, 3, 379
10 Hurley, L. H. J. Med. Chem., 1989, 32, 2027   DOI
11 Neidle, S. Biopolymers, 1997, 44, 105   DOI   ScienceOn
12 Chaires, J. B. Curr. Opin. Struct. Biol., 1998, 8, 314   DOI   ScienceOn
13 Neidle, S. Nucleic Acid Structure and Recognition. Oxford University Press, Inc., NY. 2002
14 Hahn, F. E. in Antibiotic. Mechanism of Action of Anticrobial and Antitumor Agents Corcoran, J. W.; Hahn, F. E., Eds.; Springer-Verlag: New York, U.S.A., 1975, p 79
15 Arcamonen, F.; Orezzzi, P. G.; Barbieri, W.; Nicollela, V.; Penco, S. Gazz. Chim. Ital. 1967, 97, 1097
16 van Dyke, M. W.; Hertzberg, R. P.; Dervan, P. B. Proc. Natl Acad. Sci. USA, 1982, 79, 5470   DOI   ScienceOn
17 Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. J. Mol. Biol., 1985, 183, 553   DOI
18 Pelton, J. G.; Wemmer, D. E. Biochemistry, 1988, 27, 8088   DOI
19 Chaires, J. B. Biopolymers, 1997, 44, 201   DOI   ScienceOn
20 Catalan, J.; Mo, O.; de Paz, J. L. G.; Yanez, M. J. Org. Chem. 1984, 49, 4379   DOI
21 Lown, J. W.; Krowicki, K.; Balzarini, J.; Newman, R. A.; de Clercq E. J. Med. Chem. 1989, 32, 2368   DOI
22 O'Donnell, T. J.; Chabalowski, C. F. In Computer Graphics Applied to Molecular Modelling. in New Methods in Drug Research Makriyannis, A. Prous, R., Ed.: Barcelona, Spain, 1986, Vol. 2
23 Dolenc, J.; Ostenbrink1, C.; Koller, J.; van Gunsteren, W. F. Nucleic Acids Res. 2005, 33, 725   DOI   ScienceOn
24 Lown, J. W.; Krowicki, K.; Bhat, U. G.; Skorobogaty, A,; Ward, B.; Dabrowiak, J. C. Biochemistry, 1986, 25, 7408   DOI   ScienceOn
25 Lown, J. W. Org. Prep. Proced. INT. 1989, 21 1   DOI   ScienceOn
26 Lown, J. W. Anticancer Drug Des. 1988, 3, 25
27 Lee, M.; Chang, D. K.; Hartley, J. A.; Pon, R. T.; Krowicki, K.; Lown, J. W. Biochemistry, 1988, 27, 445   DOI   ScienceOn
28 Lee, M.; Coulter, D. M.; Pon, R. T.; Krowicki, K.; Lown, J. W. Biochemistry, 1988, 5, 1059
29 Coll, M.; Aymami, J.; van der Marel, G. A.; van Boom, J. H.; Rich, A.; Wang, A. H. Biochemistry, 1989, 28, 310   DOI   ScienceOn
30 Goodsell, D. S.; Ng, H. L.; Kopka, M. L.; Lown, J. W.; Dickerson, R. E. Biochemistry, 1995, 34, 16654   DOI   ScienceOn
31 Del Bene, J. E. J. Am. Chem. Soc. 1977, 99, 3617   DOI
32 Kabir, S.; Anne-Marie, S. J. Comput. Chem. 1991, 12, 1142
33 Rao, K. E.; Bathini, Y.; Lown, J. W. J. Org. Chem. 1990, 55, 728   DOI
34 Mo, O.; de Paz, J. L. G.; Yanez, M. J. Phys. Chem. 1986, 90, 5597   DOI
35 Gaussian 98, Revision A. 7, Frich, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakzewski, V. G.; Montgomery, Jr. J. A.; Stratman, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Morokuma, Q. Cui, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Stefanov, J. V.; Ortiz, B. B.; Liashenko, G. Liu, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen. M. W.; Wong, J. L.; Andres, W.; Head-Gordon., M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1998墲֗⨀ᄀĀ돀ᣨ?⨀塨?⨀ꁩ잖⨀섚돐잖⨀잖⨀졩잖⨀餚덐?잖⨀頚砚礙돀棠?⨀塨?⨀㣆?⨀儙돐잖⨀잖⨀磆?⨀⤙댐䁽ጄȀ
36 Politzer, P. Toxicology Letters, 1988, 43, 257   DOI   ScienceOn
37 Thomson, C.; Higgins, D. Int. J. Quantum Chem.: Quantum Chem. Symp. 1988, 22, 97
38 Lee, G. Y.; Lee, H. M. J. Kor. Chem. Soc., 1998, 42, 391