On n-pi Elektron Distribution in Simple Keto-Enol tautomeric Systems: H3C-C(R)=O==H2C=C(R)-OH and RH@C-CH=O==RHC=CH-OH

• Autorzy: Raczyńska E.
• Języki publikacji: EN

Abstrakty

EN

Variations of the n- electron distribution during the tautomeric interconversion and substituent effects were analysed for simple keto-enol tautomeric systems of general formulae H3C-C(R)=O H2C=C(R)-OH and RH2C-CH=O RHC=CH-OH using the geometry-based HOMA index.

Słowa kluczowe

EN

tautomerism; n-pi electron distribution; HOMA indices; substituent effects

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 4
• Strony: 749--758
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Raczyńska E.

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

Bibliografia

• 1.Rappoport Z. (Ed), The Chemistry of Enols, Wiley, Chichester, 1990.
• 2.Toullec J., Adv. Phys. Org. Chem., 18, 1 (1982).
• 3.Shainyan B.A. and Mirskova A.N., Russ. Chem. Rev., 48, 107 (1979).
• 4.Krygowski T.M., J. Chem. Inf. Comput. Sci., 33, 70 (1993).
• 5.Taft R.W. and Topsom R.D., Prog. Phys. Org. Chem., 16, 1 (1987).
• 6.Schleyer P. v. R., Chem. Rev., 101, 1115 (2001).
• 7.a) Krygowski T.M., Cyrahski M.K., Czamocki Z., Hafelinger G. and Katritzky A.R., Tetrahedron, 56, 1783 (2000); b) Krygowski T.M. and Cyrariski M.K., Chem. Rev., 101, 1385 (2001).
• 8.Krygowski T.M., Cyrariski M.K. and Anulewicz-Ostrowska R., Polish J. Chem., 75, 1939 (2001).
• 9.a) Cyrahski M.K., Gilski M., Jaskólski M. and Krygowski T.M., J. Org. Chem., 68, 8607 (2003); b) Raczynska E.D., Darowska M., Cyrariski M.K., Makowski M., Rudka T., Gal J.-F. and Maria P.-C., J. Phys. Org. Chem., 16, 783 (2003).
• 10.Smith B.J., Nguyen M.T., Bouma W.J. and Radom L., J. Am. Chem. Soc., 113, 6452 (1991).
• 11.Turecek R and Cramer C.J., J. Am. Chem. Soc., 117, 12243 (1995).
• 12.Rodriguez-Santiago L., Vendrell O., Tejero 1., Sodupe M. and Bertran J., Chem. Phys. Let., 334, 11 (2001), and references cited therein.
• 13.Haranczyk M., Burgers P.C. and Ruttink P.J.A., Int. J. Mass Spectrom., 220, 53 (2002), and reference cited therein.
• 14.Krygowski T.M. and Cyranski M.K., Tetrahedron, 52, 1713 (1996).
• 15.Kim Y., Lim S., KimH.-J.and Kim Y., J. Phys. Chem. A, 103,617(1999).
• 16.Lammertsma K. and Prasad B.V., J. Am. Chem. Soc., 116, 642 (1994).
• 17.Komaromi I. and Tronchet J.M.J., J. Mol. Struct. (Theochem), 366, 147 (1996); Long J.A., Harris N and Lammertsma K., J. Org. Chem., 66, 6762 (2001).
• 18.Lammertsma K. and Prasad B.V., J. Am. Chem. Soc., 115, 2348 (1993).
• 19.Delaere D., Raspoet G. and Nguyen M.T., J. Phys. Chem. A, 103, 171 (1999).
• 20.Wu C.-C. and Lien M.-H., J. Phys. Chem., 100, 594 (1996).
• 21.Su C.-C., Lin C-K., Wu C.-C. and Lien M.-H., J. Phys. Chem., 103, 3289 (1999).
• 22.Hansch C., Leo A. and Taft R.W., Chem. Rev., 91, 165 (1991).
• 23.Lin J-F., Wu C.-C. and Lien M.-H., J. Phys. Chem., 99, 16903 (1995).