Change of Prototropic Equilibria for Uracil when Going from Neutral Molecule to Charged Radicals. Quantum-Chemical Studies in the Gas Phase

• Autorzy: Raczyńska E. D. , Zientara K. , Kolczyńska K. , Stępniewski T. M.
• Języki publikacji: EN

Abstrakty

EN

To understand various substitution, oxidation or degradation reactions for uracil, quantum-chem i calcalculations were performed for two classes of charged radicals (cations and anions) of uracil (U+ź and U-ź) and model compounds: phenol (P+ź and P-ź) and hydroxyazines (HP1-4+ź and HP1+-4-ź). In calculations, all possible eighteen prototropic tautomers-rotamers of U and all possible five prototropic tautomers-rotamers of P and HP1-4 were considered. Stabilities, internal effects and aromatic character, estimated for charged radicals, were compared with those observed previously for neutral molecules. The great est changes of the tautomeric preferences take place for radical anions. One-electron reduction stabilizes the keto and amide functions in studied compounds, whereas one-electron oxidation favors the enol function for ph nol and the amide function for uracil and hydroxyazines.

Słowa kluczowe

EN

uracil; hydroxyazines; charged radicals; prototropic equilibria; gas phase; AM1; DFT

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 5
• Strony: 821--834
• Opis fizyczny: Bibliogr. 24 poz., rys.

Twórcy

autor

Raczyńska E. D.

autor

Zientara K.

autor

Kolczyńska K.

autor

Stępniewski T. M.

• Department of Chemistry, Warsaw University of Life Sciences, 02-776 Warszawa, Nowoursynowska 159c, Poland,

Bibliografia

• 1.a) Pozharskii A.F., Soldatenkov A.T. and Katritzky A.R, Heterocycles in Life and Society, Wiley, New York, 1997; b) Katritzky A.R., Jug K. and Oniciu D.C., Chem. Rev., 101,1421 (2001); b) Balaban A.T, Oniciu D.C. and Katritzky A.R, Chem. Rev., 104, 2777 (2004); c) Stanovnik B, Tisler M, Katritzky A.K. and Denisko O.V., Adv. Heterocyclic Chem., 91, 1 (2006); d) Kwiatkowski J.S. and Pullman B, Adv. Heterocyclic Chem., 18,199 (1975); e) Kwiatkowski J.S. and Person W.B., In Theoreti¬cal Biochemistry and Molecular Biology, Beveridge D.L. and Lavery R. (Eds.), Academic Pu.j, New York, 1990; f) Rejnek J., Hanus M, Labelac M, Ryjacek F. and Hobza P., Phys. Chem. Chem. Phys., 7, 2006 (2005); g) Sanchez R., Giuliano B.M, Melandri S, Favero L.B. and Caminati W, J. Am. Chem. Soc, 129, 6287 (2007).
• 2. a) March J, Advanced Organic Chemistry, Reaction, Mechanism and Structure, 4th ed., Wiley J, New York, 1993; b) Carey FA. and SundbergR.J,^crva«cerf Organic Chemistry, 3rded, Plenum Press, New York, 1993; c) Weiss U. and Edwards J.M, The Biosynthesis of Aromatic Compounds, Wiley, New York, 1980; d) Haslam E, 77ie Shikimate Pathway, Halsted Press, Wdey, New York, 1974.
• 3. a) Jalbout A.F, Trzaskowski B, Xia Y, Li Y, Hu X, Li H, El-Nahas A. and Adamowicz L, Chem. Phys., 332, 152 (2007), and references cited therein; b) Kryachko E, Nguyen M.T and Zeegers-Huyskens T, J. Phys. Chem. A, 105, 1288 (2001); c) Tian S.X, Zhang C.F, Zhang Z.J, Chen X.J. and Xu K.Z., Chem. Phys., 242, 217 (1999).
• 4. a) Flossmann W, Westhof E. and Muller A, J. Chem. Phys., 64, 1688 (1976); b) Wetmore S.D, Boyd R.J. and Eriksson L.A, J. Phys. Chem. B, 102,5369 (1998); c) Chen Y. and Close D, Struct. Chem., 13, 203 (2002); d) Bachórz R.A., Rak J. and Gutowski M, Phys. Chem. Chem. Phys., 7, 2116 (2005);e) Li X, Bowen K.H, Haranczyk M, Bachórz RA, Mazurkiewicz K, Rak J. and Gutowski M., J. Chem. Phys., 127, art. no. 174309 (2007); f) Bachórz R.A, Klopper W, Gutowski M, Li X. and Bowen K.H., J. Chem. Phys., 129, art. no. 054309 (2008).
• 5. a) Raczyńska E.D, Gal J.-F, Maria P.-C, Zientara K. and Szeląg M, Anal. Bioanal. Chem., 389, 1365 (2007); b) Mallard W.G. and Linstrom P.J. (eds), NIST Chemistry WebBook. NIST Standard Reference Database. National Institute of Standards and Thechnology, Gaithersburg, 2005.
• 6. a) Glossary of Terms Used in Physical Organic Chemistry, IUPAC Recommendations, 1994; b) Gold V, PureAppl. Chem., 51, 1725 (1979).
• 7. a) Raczyńska E.D., Zientara, K, Kolczyńska K. and Stępniewski T, J. Mol. Struct. (Theochem), 894, 103 (2009); b) Raczyńska E.D., Zientara K, Stępniewski T. and Kolczyńska K, Collect. Czech Chem. Commun. (in the press).
• 8. a) Cyrański M.K, Gilski M, Jaskólski M. and Krygowski TM, J. Org. Chem., 68, 8607 (2003);b) Raczyńska E.D., Kosińska W, Ośmiałowski B. and Gawinecki R, Chem. Rev., 105,3561 (2005), and references cited therein.
• 9. a) Piskur J, Schnackerz K.D., Andersen G. and Bjornberg O, Trends Gen., 23, 369 (2007); b) Sousa M.M.L, Krokan H.E. and Slupphaug G, Mol Aspects Med., 28,276 (2007); c) Singh H.K, Saquib M, Haque MM. and Muneer M, J. Hazardous Mat., 142,425 (2007); d) Dhananjeyan M.R., Annapoorani R. and Renganathan R, J. Photochem. Photobiol. A: Chem., 109, 147 (1997); e) Annapoorani R, Dhananjeyan M.R. and Renganathan R, J. Photochem. Photobiol. A: Chem., Ill, 215 (1997); f) Chabita K, Basu S, Mandal P.C. and Bhattacharyya S.N, Radiat. Phys. Chem., 51, 93 (1998), and references cited therein; g) van Gennip A.H., Abeling N.G.G.M., Vreken P. and van Kuilenburg A.B.P, J. Inher Metah. Dis., 20, 203(I??7).
• 10. DewarM.J.S., Zoebisch E.G., HealyE.F. and Stewart J.J.P., J. Am. Chem. Sac, 107, 3902 (1985).
• 11. Parr R.G. and Yang W, Density Functional Theory of Atoms and Molecular Orbital Theory, Oxford Uni¬versity Press, New York, 1989.
• 12. a) Becke A.D., J. Chem. Phys., 98,5648 (1993); b) Lee C., Yang W. and Parr R.G., Phys. Rev. B, 37,785 (1988).
• 13. a) Sygula A., J. Chem. Res. (S), 56 (1989); b) Fabian W.M.F., J. Comput. Chem., 12, 17 (1991);c) Szafran M., Karelson MM, Katritzky A.R, Koput J. and Zemer M.C, J. Comput. Chem., 14, 371 (1993); d) Orgetir C. and Yaman M., J. Mol. Struct. (Theochem), 458, 217 (1999); e) Allegretti P.E., Milazzo C.B, Castro E.A. and Furlong J.J, J. Mol. Struct. (Theochem), 589-590,161 (2002); f) Böhm S, Fiedler P. and Exner O, New J. Chem., 28,67 (2004); g) Fiedler P., Böhm S, Kulhanek J. and Exner O, Org. Biomol. Chem., 4,2003 (2006); h) Exner O. and Böhm S, Collect. Czech. Chem. Commun., 71, 1239 (2006).
• 14. a) Hehre W.J, Radom L, Schleyer P.v.R. and Pople J. A., Ab initio Molecular Theory, Wiley, New York, 1986; b) Jensen F, Introduction to Computational Chemistry, John Wiley & Sons, New York, 1999.
• 15. a) Kruszewski J. and Krygowski T.M., Tetrahedron Lett., 3839 (1972); b) Krygowski T.M. and Kruszewski J, Bull. Acad. Polon. Sei., Ser. Sei. Chim., 21,409 (1973).
• 16. Krygowski T.M., J. Chem. Int. Comput. Sei., 33, 70 (1993).
• 17. HyperChem, Autodesk Inc., Sansalito CA 94965, USA, 1992.
• 18. Firsch M. J, Trucks G.W, Schlegel H.B, Scuseria G.E., Robb M. A, Cheeseman J.R, Montgomery J. A. Jr., Vreven T., Kudin K.N., Burant J.C, Millam J.M, Iyengar S.S., Tomasi J., Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson R, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Kiene M, Li X, Knox J.E, Hratchian H.P., Cross J.B, Bakken V, Adamo C, Jaramillo R, Gomperts R, Stratmann R.E., Yazyev O, Austin A.J., Cammi R, Pomelli C, Ochterski J.W, Ayala P.Y, Morokuma K, Voth G.A., Salvador P, Dannenberg J.J, Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C, Farkas O., Malick D.K., Rabuck A.D., Raghavachari K, Foresman J.B, Oritz J.V., Cui Q, Baboul A.G., Clifford S, Cioslowski J, Stefanov B.B, Liu G, Liashenko A., Piskorz P, Komaromi I, Martin R.L, Fox D.J, Keith T, Al-Laham MA, Peng C.Y., Nanayakkara A, Challacombe M, Gill P.M.W, Johnson B, Chen W, Wong M.W, Gonzalez C. and Pople JA, Gaussian-03, Revision E.Ol, Gaussian, Inc., Wallingford CT, 2004.
• 19. Kaiser E.T and Kevan L. (eds.), Radical Ions, Interscience, New York, 1968.
• 20. a)RothH.D., Topic Current Chem., 163,131 (1992);b)Davies A.G., Chem. Soc. Rev., 22,299 (1993); c) Lam A.K.Y, Abrahams B.F., Grannas MJ, McFadyen W.D. and O'Hair RA.J., Dalton Trans., 5051(2006) ; d) Schafer M, Drayss M, Springer A, Zacharias P. and Meerholz K., Eur. J. Org. Chem., 5162 (2007) ; e) Turecek F., Eur. J. Mass Spectrom., 13, 89 (2007); f) Wolken J.K, Yao C, Turecek F, Polce M.J. and Wesdemiotis C, Int. J. Mass Spectrom., 267, 30 (2007).
• 21. a) Lefler J.E. and Grunwald E., Rates and Equilibria of Organic Reactions, John Wiley and Sons, Inc., New York and London, 1963, ch. 6; b) Exner O, In Advances in Linear Free Energy Relationships, Plenum Press, London & New York, 1972, ch. 1.
• 22. Le H.T., Flammang R, Gerbaux P, Bouchoux G. and Nguyen M.T., J. Phys. Chem. A, 105, 11582 (2001).
• 23. a) Roca-Sanjuän D, Rubio M., MerchänM. and Serrano-Andres L, J. Chem. Phys., 125, art. no. 084302 (2006); b) Roca-Sanjuän D, Merchän M, Serrano-Andres L. and Rubio M.,J. Chem. Phys., 129, art. no. 095104 (2008).
• 24. a) Raczyńska E.D, Polish J. Chem., 73, 1863 (1999); b) Raczyńska E.D, Polish J. Chem., 74, 1283 (2000).