A study on tautomerism of dihydroxypyrimidines

Yıl 2005, Cilt: 1 Sayı: 4, 55 - 70, 01.02.2005

Alaattin Güven

https://izlik.org/JA99NG52CC

Öz

Anahtar Kelimeler

-

A study on tautomerism of dihydroxypyrimidines

https://izlik.org/JA99NG52CC

Öz

dihidroksipirimidin ve 4,5-dihidroksipirimidine ait tatomerik dengeler yarı-ampirik AM1, PM3, PM5 veyüksek seviyede B3LYP/6-31G(d) ve B3LYP/6-311++G(d,p) yöntemleri kullanarak incelenmifltir.Hesaplamalardan elde edilen sonuçlar mevcut deneysel veriler ile oldukça iyi uyum göstermifltir

Anahtar Kelimeler

pirimidin , tatomerik denge , konformasyon , AM1 , PM3 , PM5 , B3LYP , IEFPCM , COSMO

Kaynakça

• Katritzky, A.R.; Lagowski, J.M. Advances in Heterocyclic Chemistry, 1963, 1-81, 311-437.
• Elguero,J.; Marzin, C.; Katritzky, A.R.; Linda, P. The Tautomerism of Heterocycles; Academic Press: New York, 1976.
• Beak, P.; Fry, F.S.; Lee, Jr.J.; Steele, F. J. Am. Chem. Soc., 1976, 98, 171.
• Spinner, E.; Yeoh, G.B. J. Chem. Soc. (B), 1971, 296.
• Bean, G.P.; Cook, M.J.; Dand, T.M.; Katritzky, A.R.; Lea, J.R. J. Chem. Soc. (B) 1971, 2338.
• Cook, M.J.; Katritzky, A.R.; Linda, P.; Tack, R.D. J. Chem. Soc., Perkin Trans. 2, 1972, 1295.
• Cook, M.J.; Katritzky, A.R.; Linda, P.; Tack, R.D. J. Chem. Soc., Perkin Trans. 2, 1973,1080.
• Lapinski, L.; Nowak, M.J.; Fulara, J.; Les, A.; Adamowicz, L. J. Phys. Chem., 1992, 96, 6250.
• Katritzky, A.R. Chimia, 1970, 134.
• Cravero, R.M.; Sierra, M.G.; Olivieri, A.C. J. Chem. Soc., Perkin Trans. 2, 1993, 1067.
• Parchment, O.G.; Hillier, I.H.; Green, D.V.S., J. Chem. Soc. Perkin Trans. 2, 1991, 799.
• Anandan, K.; Kolandaivel P.; Kumaresan R. J. Mol. Struct. (Theochem), 2004, 686, 83.
• Greenwood, J.R.; Capper, H.R.; Allan, R.D.; Johnston, G.A.R. J. Mol. Struct. (Theochem), 1997, 419, 97.
• Karelson, M.M.; Katritzky, A.R.; Szafran M.; Zerner M.C. J. Org. Chem., 1989, 54, 6030.
• Yekeler, H. J. Mol. Struct. (Theochem), 2005, 713, 201.
• Katritzky, A.R.; Karelson, M., J. Am. Chem. Soc., 1991, 113, 1561.
• El-Nahas, A.M.; Hirao, K. J. Mol. Struct. (Theochem), 1999, 459, 229.
• Les, A.; Adamowicz, L. J. Am. Chem. Soc., 1990, 112, 1504.
• Trifonov, R.E.; Alkorta I.; Ostrovskii V.A.; Elguero J. J. Mol. Struct. (Theochem), 2004, 668, 123.
• Gould, I.R.; Burton, N.A.; Hall, R.J.; Hillier I.H. J. Mol. Struct. (Theochem), 1995, 331, 147.
• Leszczynski, J.; Sponer J. J. Mol. Struct. (Theochem), 1996, 388, 237.
• Fabian, W.M.F. J. Compt. Chem., 1991, 12, 17.
• Marshall, G.J.R.; Walker, J., J. Chem. Soc., 1951,1004.
• Parry, G.S. Acta Cryst., 1954, 7, 313.
• Hoogsteen, K. Acta Cryst. 1960, 13, 1050.
• Katritzky, A.R.; Waring, A.J. J. Chem. Soc., 1962, 1540.
• Beak, P.; White, M. J. Am. Chem. Soc., 1982, 104, 7073.
• Tsuchiya, Y.; Tamura, T.; Fujii M.; Ito, M. J. Phys. Chem., 1988, 92, 1760.
• Scanlan, M.J.¸Hillier, I.H. J. Chem. Soc., Chem. Commun., 1984, 102.
• Leszczynski, J.; Sponer J. J. Mol. Struct. (Theochem), 1996, 388, 237.
• Tanner, E.M. Spectrochim Acta, 1956, 8, 9.
• Brown, D.J.; Teitei, T., Aust. J. Chem., 1964, 17, 567.
• Kheifets, G.M.; Khromov-Borisov, N.U. Zh. Obshch. Khim., 1964, 34, 3134.
• Inoue, Y.; Furutachi, N.; Nakanishi, K. J. Org. Chem., 1966, 31, 175.
• Kheifets, G.M.; Khromov-Borisov, N.U.; Koltsov, A.I. Dokl.Akad. Nauk SSSR, 1966, 166, 635.
• Kheifets, G.M.; Khromov-Borisov, N.U.; Koltsov, A.I.; Volkenstein, M.V. Tetrahedron, 1967, 23, 1197.
• Katritzky, A.R.; Popp, F.D.; Waring, A.J. J. Chem. Soc., B, 1966, 565.
• Hurst, D.T.; McOmie, J.F.W.; Searle, J.B. J. Chem. Soc., 1965, 7116.
• Budesinsky, Z.; Prikryl, J.; Suatek, E., Collect. Czech. Chem. Commun., 1967, 32, 1637 ().
• Brederech, H.; Effenberger, F.; Österlin, H.G., Chem. Ber., 1967, 100, 2280.
• Dewar, M.J.S. J. Am. Chem. Soc., 1985, 107 3902.
• Stewart, J. J. P. J. Comp. Chem., 1989, 10, 209.
• Stewart, J.J.P., Fujitsu Limited, Tokyo, Japan. Stewart, J.J.P. J. Mol. Model., 2004, 10, 6.
• Stewart, J.J.P., Fujitsu Limited, Tokyo, Japan. ChemOffice CambridgeSoft Corporation 100 Cambridge Park Drive Cambridge, MA 021140 USA
• Beke, A.D., Phys. Rev. A., 1998, 38, 3098.
• Lee, C.; Wang, Y.; Parr, R.G., Phys. Rev. A., 1988, 45 785.
• Wong, M.W.; Frisch, M.J.; Wiberg, K.B., J. Am. Chem. Soc., 1991, 113, 4776.
• James B. Foresman and Æleen Frisch, Exploring Chemistry with Electronic Structure Methods, 2.Ed., Gaussian Inc., Pittsburg, 1996.