The oretical study on the molecular tautomerism of the 3-hydroxy-pyridin-4- one system

Molecular Physics

Volumn 111, Issue 8, 2013, Pages 958-967

  Zborowski, Krzysztof K ^a   Mohammadpour, Mehrdad ^b   Sadeghi, Amir ^b   Proniewicza, Leonard M ^a,c  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b ISFAHAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c State Higher Vocational School in Tarnow   (Poland)

Author keywords

AIM energy partition; Aromaticity; Equilibrium constants; Pyridin 4 ones; Tautomerism

Indexed keywords

AROMATICITIES; CO-ORDINATION CHEMISTRIES; ENERGY PARTITION; HARMONIC OSCILLATOR MODEL OF AROMATICITY; INTRA-MOLECULAR HYDROGEN BONDS; NUCLEUS INDEPENDENT CHEMICAL SHIFTS; PYRIDIN-4-ONES; TAUTOMERISM;

AROMATIC COMPOUNDS; COORDINATION REACTIONS; EQUILIBRIUM CONSTANTS; HYDROGEN BONDS; METAL IONS; MOLECULAR STRUCTURE; MOLECULES; OSCILLATORS (MECHANICAL); QUANTUM CHEMISTRY;

AROMATIZATION;

EID: 84880268680     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268976.2012.760052     Document Type: Article

References (59)

1. L. Merson and N. Olivieri, Blood Rev. 16, 127 (2002).
2. Y. Rombos, R. Tzanetea, K. Konstantopoulos, S. Simitzis, C. Zervas, P. Kyriaki, M. Kavouklis, A. Aessopos, N. Sakelleropoulos, M. Karagiorga, V. Kalotychou, and D. Loukopoulos, Haematologica 85, 115 (2000).
3. Stedman's Medical Dictionary, 27th ed. (Williams & Wilkins, Baltimore, CA, 2000).
4. M. Melchior, S.J. Rettig, B.D. Liboiron, K.H. Thompson, V.G. Yuen. J.H. McNeill, and C. Orvig, Inorg. Chem. 40, 4686 (2001).
5. R.A. Yokel, Neurotoxicity 21, 813 (2000).
6. M.A. Green and M.J. Welch, Nucl. Med. Biol. 16, 435 (1989).
7. IUPAC Gold Book: Tautomerism. http://goldbook.iupac. org/T06252.html
8. M. Mohammadpour (private communication).
9. M. Sraga, K. Zborowski, T. Kiss and L.M. Proniewicz, Ann. Pol. Chem. Soc. 2, 931 (2003).
10. C.C.J. Roothaan, Rev. Mod. Phys. 23, 69 (1951).
11. C. Møller and M.S. Plesset, Phys. Rev. 46, 0618 (1934).
12. B. Miehlich, A. Savin, H. Stoll, and H. Preuss, Chem. Phys. Lett. 157, 200 (1989).
13. C. Adamo and V. Barone, J. Chem. Phys. 108, 664 (1998).
14. J.P. Perdew, J.A. Chevary, S.H. Vosko, K.A. Jackson, M.R. Pederson, D.J. Singh, and C. Fiolhais, Phys. Rev. B 46, 6671 (1992).
15. A.D. Becke, J. Chem. Phys. 98, 5648 (1993).
16. Gaussian 09 User's Reference. http://www.gaussian.com/g-tech/g-ur/k-dft. htm
17. Y. Zhao and D.G. Truhlar, Theor. Chem. Acc. 120, 215 (2008).
18. S. Grimme, J. Chem. Phys. 124,034108 (2006).
19. T. Schwabe and S. Grimme, Phys. Chem. Chem. Phys. 8, 4398 (2006).
20. J.A. Pople, M. Head-Gordon, D.J. Fox, K. Raghavachari, and L.A. Curtiss, J. Chem. Phys. 90, 5622 (1989).
21. L.A. Curtiss, C. Jones, G.W. Trucks, K. Raghavachari, and J.A. Pople, J. Chem. Phys. 93, 2537 (1990).
22. L.A. Curtiss, K. Raghavachari, G.W. Trucks, and J.A. Pople, J. Chem. Phys. 94, 7221 (1991).
23. L.A. Curtiss, K. Raghavachari, P.C. Redfern, V. Rassolov, and J.A. Pople, J. Chem. Phys. 109, 7764 (1998).
24. L.A. Curtiss, P.C. Redfern, and K. Raghavachari, J. Chem. Phys. 126, 084108 (2007).
25. J.A. Montgomery Jr., M.J. Frisch, J.W. Ochterski, and G.A. Petersson, J. Chem. Phys. 112, 6532 (2000).
26. J.A. Montgomery Jr., M.J. Frisch, J.W. Ochterski, and G.A. Petersson, J. Chem. Phys. 110, 2822 (1999).
27. J.W. Ochterski, G.A. Petersson, and J.A. Montgomery Jr., J. Chem. Phys. 104, 2598 (1996).
28. R. Krishnan, J.S. Binkley, R. Seeger and J.A. Pople, J. Chem. Phys. 72, 650 (1980).
29. T.H. Dunning Jr., J. Chem. Phys. 90, 1007 (1989).
30. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg,M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O? . Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian 09, Revision A.02 (Gaussian, Inc., Wallingford, CT, 2009).
31. P. Hobza and J. Sponer, Chem. Rev. 99, 3247 (1999).
32. J.W. Ochterski, Thermochemistry in Gaussian (Gaussian White Papers). http://www.gaussian.com/g-whitepap/thermo.htm
33. P.vR. Schleyer, C. Marker, A. Dransfeld, H.J. Jiao, and N.J.R.V. Hommes J. Am. Chem. Soc. 118, 6317 (1996).
34. P.vR. Schleyer, M. Manoharan, Z.X. Wang, B. Kiran, H.J. Jiao, R. Puchta, and N.J.R.V. Hommes Org. Lett. 3, 2465 (2001).
35. C. Corminboeuf, T. Heine, G. Seifert, P.vR. Schleyer, and J. Weber, Phys. Chem. Chem. Phys. 6, 273 (2004).
36. K. Wolinski, J.F. Hilton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990)
37. T.M. Krygowski, J. Chem. Inf. Comp. Sci. 33, 70 (1993).
38. M. Palusiak and T.M. Krygowski, Chem. Eur. J. 13, 7996 (2007).
39. J. Poater, X. Fradera, M. Duran, and M. Sola, Chem. Eur. J. 9, 400 (2003).
40. P. Bultinck, M. Rafat, R. Ponec, B. van Gheluve, R. Carbo-Dorca, and P. Popelier, J. Phys. Chem. A 110, 7642 (2006).
41. P.v.R. Schleyer and F. Puhlhofer, Org. Lett. 4, 2873 (2002).
42. R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Clarendon Press, Oxford, 1990).
43. F.W. Bieglerkonig, R.F.W. Bader, and T.H. Tang, J. Comput. Chem. 3, 317 (1982).
44. T.A. Keith, AIMAll, version 11.10.16 (TK Gristmill Software, Overland Park, KS, 2011. aim.tkgristmill.com
45. J.P. Foster and F. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980).
46. W. Yan, Y. Xue, H. Zhu, J. Zeng, and D. Xie, J. Comput. Chem. 25, 1833 (2004).
47. V.M.F. Morris, M.S. Miranda, and M.A.R. Matos, J. Chem. Thermodyn. 38, 450 (2006).
48. T.M. Krygowski and M.K. Cyránski, Tetrahedron 52, 1713 (1996).
49. M.K. Cyránski, Chem. Rev. 105, 3773 (2005).
50. K.K. Zborowski, M. Sola, J. Poater, and L.M. Proniewicz, J. Phys. Org. Chem. 24, 499 (2011).
51. U. Koch and P.L.A Popelier, J. Phys. Chem. 99, 9747 (1995).
52. P.L.A. Popelier, J. Phys. Chem. A 102, 1873 (1998).
53. O. Ḿo and M. Yanez, J. Phys. Chem. A 102, 8174 (1998).
54. I. Rozas, I. Alkorta, and J. Elguero, J. Phys. Chem. A 105, 10462 (2001).
55. K.K. Zborowski and L.M. Proniewicz, J. Phys. Org. Chem. 21, 207 (2008).
56. K.K. Zborowski, Chem. Phys. Lett. 545, 144 (2012).
57. K.K. Zborowski, R. Grybós, A. Wesełucha-Birczýnska, Y. Kim, and L.M. Proniewicz, Mol. Phys. 110, 343 (2012).
58. K.K. Zborowski, R. Grybós, and L.M. Proniewicz, J. Mol. Struct. (Theochem) 639, 87 (2003).
59. K.K. Zborowski, A. Korenova, M. Uher, and L.M. Proniewicz, J. Mol. Struct. (Theochem) 683, 15 (2004