Angular Group Induced Bond Alternation (AGIBA). Part VII. The Case of a Branched Substituent - the Carboxylic Group

• Autorzy: Krygowski T. , Pindelska E.
• Języki publikacji: EN

Abstrakty

EN

Angular groups attached to aromatic rings cause an increase of the double bond localization, called Angular Group Induced Bond Alternation (AGIBA). The effect for the groups with single bonds, X-Y, increases the double bond character of the cis CC bond in the ring, whereas the groups with double bonds, X=Y, work in the opposite way. The group with a branched structure, like the carboxylic one, should exhibit an enhancement of the AGIBA effect. Analyses of 61 geometries for p-substituted derivatives of benzoic acid, as well as of the geometry of benzoic acid optimized at B3LYP/6-311G** level of theory, show that there is no cooperative effect in this kind of substituent.

Słowa kluczowe

EN

ab initio calculations; benzoic acid; substituent effect; double bond localization

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 2-3
• Strony: 325--329
• Opis fizyczny: Bibliogr. 30 poz., rys.

Twórcy

autor

Krygowski T.

• Department of Chemistry, University of Warsaw, 02 923 Warsaw, Pasteura 1, Poland

autor

Pindelska E.

• Department of Chemistry, University of Warsaw, 02 923 Warsaw, Pasteura 1, Poland

Bibliografia

• 1.Krygowski T.M.,Anulewicz R.,Jarmuła A.,Bąk T., Rasała D. and Howard S.T., Tetrahedron, 50,13155 (1994).
• 2.Howard S.T., Krygowski T.M. and Główka M.L., Tetrahedron, 52,11379 (1996).
• 3.KrygowskiT.M.,Howard S.T.,Martynowski D.and Główka M.L., J. Phys. Org. Chem., 10,125(1997).
• 4.Krygowski T.M., Anulewicz R. and Hiberty P.C.,J. Org. Chem., 61, 8533 (1996).
• 5.Krygowski T.M., Wisiorowski M., Howard S.T. and Stolarczyk L.Z., Tetrahedron, 53,13027 (1997).
• 6.Howard S.T., Krygowski T.M., Ciesielski A. and Wisiorowski M., Tetrahedron, 54, 3533 (1998).
• 7.Krygowski T.M., Pindelska E.,Cyrański M.K. and Grabowski S.J., Tetrahedron, 56, 8715 (2000).
• 8.Boese R., Polk M. and Blaser D.,Angew. Chem. Int. Ed. Engl., 28,245 (1987).
• 9.Maulitz A.H. Stellberg P. and Boese R., J. Mol. Struct., 338,131 (1995).
• 10.Krygowski T.M., AnulewiczR. and KruszewskiJ., ActaCryst.,B39, 732 (1983).
• 11.Krygowski T.M., Anulewicz R. and Wisiorowski M., Polish J. Chem., 69,1579 (1995).
• 12.Walsh A.D., Disc. Farad. Soc., 2,18 (1947).
• 13.Bent H.A., Chem. Rev., 61,275 (1961).
• 14.Mills W.H. and Nixon I.G., J. Chem. Soc., 2510 (1930).
• 15.Boese R., Blaeser D., Billups W.E., Haley M.M., Maulitz A.H., Mohler D.L. and Vollhardt K.P.C., Angew. Chem. Int. Ed. Engl, 33, 313 (1994).
• 16.Stanger A.,J. Am. Chem. Soc, 113, 8277 (1991).
• 17.Maksić Z.B., Eckert-Maksić M., Hodoscek M., Koch W. and Kovacek D., in Molecules in Natural Science and Medicine, Maksić Z.B. and Eckert-Maksić M.,(Eds.), Ellis Horwood,Chichester, 1991,p. 334.
• 18.Siegel J., Angew. Chem. Int. Ed., 33, 1721 (1994).
• 19.Koch W, Eckert-Maksić M. and Maksić Z.B., Int. J. Quant. Chem., 48,319 (1993).
• 20.Stanger A., J. Am. Chem. Soc, 120,12034 (1998).
• 21.Allen F.H., Bellard S., Brice M.D., Cartwright B.A., Doubleday A., Higgs H., Hummelink T.W.A., Hummelink-Peters B.G.M.C, Kennard O., Motherwell W.D. S., Rodgers J.R. and Watson D.G., Acta Cryst., 835,2331(1979).
• 22.Bernstein J., in Accurate Molecular Structures—Their Determination and Importance, A. Domenicano and I. Hargittai, (Eds.), Oxford University Press, 1992, p. 489.
• 23.Pindelska E., Krygowski T.M., Anulewicz R., Cyranski M.K. and Nowacki J., J. Phys. Org. Chem., in press.
• 24.Exner O., in Correlation Analysis in Chemistry-Recent Advances, Chapman N.B. and Shorter J., (Eds.), Plenum Press, London, 1978, p. 439.
• 25.Cochran W.G. and Snedecor G.W., Statistical Methods,The Iowa State University Press, Ames, 1973, p.59.
• 26.Leiserowitz L., ActaCryst., B32, 775 (1976).
• 27.Chojnacki H., this issue, Polish J. Chem., 76, 295 (2002) and references therein.
• 28.Anulewicz R., Wawer I., Krygowski T.M., Mannele F. and Limbach H.-H., J. Am. Chem. Soc, 119, 12223 (1997).
• 29.Krygowski T.M., Pindelska E., Anulewicz-OstrowskaR., Grabowski S.J. and Dubis A., J. Phys. Org. Chem., 14,349(2001).
• 30.Frisch M.J., Trucks GW, Schlegel H.B., Gili PMW,Johnson BG, Robb M.A., Cheesman JR, KeithT, Peterson G.A., Montgomery J.A., Raghavachari K., Al-Laham M.A., Zakrzewski V.G., Ortiz J.V., Foresman J.B.,Ciosłowski J., Stefanov B.B., Nanayakkara A., Challacombe M., Peng C.Y., Ayala P.Y., ChenW, Wong MW, AndresJ.L.,Replogle E.S., Gomperts R., Martin R.L., Fox D.J.,Binkley J.S., Defrees D.J.,Baker J., Stewart J.P, .Head-Gordon M, Gonzales C, Pople J.A. , Gaussian 94; Gaussian inc. Pittsburgh PA, 1995.