On n-pi Electron Distribution in Simple Acyclic Tetrad and Pentad Tautomeric Systems

• Autorzy: Raczyńska E.
• Języki publikacji: EN

Abstrakty

EN

Variations of the n-pi electron distribution during the tautomeric interconversion were analysed for simple acyclic tetrad and pentad tautomeric systems using the geometry- based HOMA index. Internal effects such as Y-conjugation, push-pull effect and intramolecular H-bonding were discussed.

Słowa kluczowe

EN

tautomerism; tetrad and pentad systems; n-pi electron distribution; HOMA indices

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 6
• Strony: 1003--1013
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Raczyńska E.

• Department of Chemistry, Agricultural University (SGGW), ul. Nowoursynowska 159c, 02-776 Warszawa, Poland

Bibliografia

• 1.Carey F.A. and Sundberg R.J., Advanced Organic Chemistry, 3rd ed., Plenum Press, New York, 1993.
• 2.Saenger W., Principles of Nucleic Acid Structure, Springer, New York, 1994.
• 3.a) Pauling L. and Wheland G.W., J. Chetn. Phys., 1, 362 (1933); b) Pauling L., The Nature of tt Chemical Bond, 3rd ed., Cornell University Press, New York, 1960; c) Hiickel E., Z. Phys., 70, 2( (1931); d) Shaik S., Shurki A., Danovich D. and Hiberty P.C., Chem. Rev., 101, 1501 (2001).
• 4.a) Katritzky A.R., Jug K. and Oniciu D.C., Chem. Rev., 101,1421 (2001); b) Balaban A.T., Oniciu D. and Katritzky A.R., Chem. Rev., 104, 2777 (2004).
• 5.Raczynska E.D., Polish. J. Chem., 79, 749 (2005).
• 6.Krygowski T.M., J. Chem. Inf. Comput. Sci., 33, 70 (1993).
• 7.Schleyer P. v. R„ Chem. Rev., 101, 1115 (2001).
• 8.a) Krygowski T.M. and Cyraiiski M.K., Chem. Rev, 101, 1385 (2001); b) Krygowski T.M., Cyraiis M.K. and Anulewicz-Ostrowska R., Polish J. Chem., 75, 1939 (2001); c) Anulewicz R., Krygows T.M. and Jagodziriski T., Polish J. Chem., 72, 439 (1998).
• 9.a) Olah G.A. and White A.M„J. Am. Chem. Soc., 90,1884 (1968); b) Olah G.A., Burrichter A., Rasul C Hachoumy M. and Prakash G.K.S., J. Am. Chem. Soc., 119, 12929 (1997).
• 10.Gund P., J. Chem. Educ., 49, 100(1972).
• 11.Raczyńska E.D., Cyrański M.K., Gutowski M., Rak J., Gal J.-F., Maria P.-C., Darowska M. and Due mal K.,J. Phys. Org. Chem., 16, 91 (2003).
• 12.Gobbi A. and Frenking G., J. Am. Chem. Soc., 115, 2362 (1993).
• 13.a) Amekraz B., Tortajada J., Morizur J.-P., Gonzalez A.I., M6 O., Yanez M., Lcito 1., Maria P.-C. a Gal J.-F., New J. Chem., 20, 1011 (1996); b) Caminiti R, Pieretti A., Bencivenni L., Ramondo F. a Sanna N., J. Phys. Chem., 100, 10928 (1996).
• 14.Su C.-C., Lin C.-K., Wu C.-C. and Lien M.-H., J. Phys. Chem. A, 103, 3289 (1999).
• 15.Gonzalez A.I., M6 O., Yanez M., Leon E., Tortajada J., Morizur J.P., Leito I., Maria P.-C. and Gal J.- J. Phys. Chem., 100, 10490 (1996).
• 16.Krygowski T.M., Anulewicz R., Raczynska E.D. and Laurence C., J. Phys. Org. Chem., 4,689 (1991).
• 17.Krygowski T.M. and Wozniak K., in The Chemistry of Amidines and Imidates, vol. 2, Patai S. a Rappoport Z. (eds.), Wiley, Chichester, 1991, chapt. 2.
• 18.Hansch C., Leo A. and Taft R.W., Chem. Rev., 91, 165 (1991).
• 19.Wu C.-C. and Lien M.-H., J. Phys. Chem., 100, 594 (1996).
• 20.Wheland G., Resonance in Organic Chemistry, Wiley, New York, 1955.
• 21.Sklenak S., Apeloig Y. and Rappoport Z., J. Am. Chem. Soc., 120, 10359 (1998).
• 22.a) Stinchcomb D.M. and Pranata J., J. Mol. Struct. (Theochem),370,25 (1996); b) WuD.-H.and Ho J.-J. Phys. Chem. A, 102, 3582 (1998).
• 23.a) Larsen I.K., Acta Crystallogr. B, 44, 527 (1988); b) Lipczynska-Kochany E. and Iwamura H., J. Org. Chem., 47, 5277 (1982).
• 24.Delchev V.B. and Nikolov G.S., Monatsh. Chem., 131, 99 (2000).
• 25.Nagashima N., Kudoh S., Takayanagi M. and Nakata M., J. Phys. Chem., 105, 10832 (2001); and references cited therein.
• 26.Gonzalez L„ Mo O. and Yafiez M., J. Org. Chem. A, 64, 2314(1999).
• 27.Fischer G. and Fabian J., Zeitschrift Phys. Chem., 209, 93 (1999).
• 28.BuemiG.,ZuccarelloF., Venuvanalingam P. and Ramalingam M., Theor. Chem. Acc., 104,226(2000).
• 29.Gilli G., Bertulucci F., Ferretti V. and Bertolasi V., J. Am. Chem. Soc., Ill, 1023 (1989).