Powiadomienia systemowe
- Sesja wygasła!
Tytuł artykułu
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
Experimental geometry of 1,3,5-triformylobenzene and the optimized geometry of mono, meta- and para- diformylo - and 1,3,5-triformylo- benzene deriva tives were used for analysis of structural and energetic consequences of angular group induced bond alternation (AGIBA) effect of substituent. The effect is mostly observed by a substantial imbalance of the Kekulé structures of the ring in molecules in questions - the cis-type bonds in the ring in respect to CO bond in the formyl groups are al ways longer than the trans ones. Energetic differences between molecules with and with out AGIBA ef fects are rather small. Key words: substituent effect, pi-electron delocalization, canonical structures, AGIBA
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
1999--2007
Opis fizyczny
Bibliogr. 22 poz., rys.
Twórcy
autor
autor
autor
autor
- Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland, tmkryg@chem.uw.edu.pl
Bibliografia
- 1. a) Krygowski T.M., Anulewicz R., Jarmula A., Bak T., Rasała D. and Howard S.T., Tetrahedron, 46,13155 (1994); b) Howard S.T., Krygowski T.M. and Główka M.L., Tetrahedron, 52, 11379 (1996);c) Krygowski T.M., Anulewicz R. and Hiberty P.C., J. Org. Chem., 61, 8533 (1996).
- 2. Krygowski T.M. and Stępień B.T., Chem. Rev., 105, 3482 (2005).
- 3. a) Exner O., in: Advances in Linear Free Energy Relationships, Chapman N.B. and Shorter J., Eds.,Plenum Press: New York 1972, chpt. l, p. IfT; b) Exner O., in: Correlation Analysis of Chemical Data,Chapman N.B. and Shorter J., Eds., Plenum Press: New York 1988, chpt. 10, p. 439fF; c) Hansch C.,Leo A. and Taft R.W., Chem. Rev., 91, 165 (1991); d) Shorter J., Pure Appl. Chem., 66, 2451 (1994);e) Shorter J., PureAppl. Chem., 69, 2497 (1997).
- 4. Exner O. and Krygowski T.M., Chem. Soc. Rev., 25, 71 (1996).
- 5. a) Krygowski T.M., Wisiorowski M., Howard S.T. and Stolarczyk L.Z., Tetrahedron, 53,13027 (1997); b) Howard S.T., Krygowski T.M., Ciesielski A. and Wisiorowski M., Tetrahedron, 54, 3533 (1998);c) For review see: Krygowski T.M. and Cyrański M.K., Synlett, 7, 922 (2003).
- 6. a) Krygowski T.M., Howard S.T., Martynowski D. and Główka M.L., J. Phys. Org. Chem., 10, 125 (1997); b) Krygowski T.M., Piętka E., Anulewicz R., Cyrański M.K. and Nowacki J., Tetrahedron, 54, 12289(1998).
- 7. Kirillov S.A., Morresi A., Paolantoni M. and Sassi P., J. Phys. Org. Chem., 20, 568 (2007).
- 8. Wiberg K.B., Acc. Chem. Res., 32, 922 (1999).
- 9. Arnold Z. and Žemlička J., Coll. Czechoslov. Chem. Commun., 25, 1318 (1960).
- 10. Oxford Diffraction (2001). CrysAlis CCD and CrysAlis RED. Version 1.171.27p5 beta. Oxford Diffraction Ltd., Wrocław, Poland.
- 11. Sheldrick G.M., Acta Crystallogr. A, 46, 467 (1990).
- 12. Sheldrick G.M., SHELXL93. Program for the Refinement of Crystal Structure; University of Göetingen: Germany, 1993.
- 13. Frisch M.J., Trucks G.W, Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven Jr. T., Kudin K.N., Burant J.C., Millam J.M., lyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y, Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., 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., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi L, Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y, Nanayakkara A., Challacombe M., Gili P.M.W., Johnson B., Chen W, Wong M.W, Gonzalez C. and Pople J.A., Gaussian, Inc., Wallingford CT, 2004.
- 14. Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H. and van Eikema Hommes N.J.R., J. Am. Chem. Soc., 118,6317(1996).
- 15. Schleyer P.v.R., Jiao H., van Eikema Hommes N. J.R., Malkin V.G. and Malkina O.L., J. Am. Chem. Soc.,119, 12669 (1997).
- 16. For review see: Chen Z., Wannere C.S., Corminboeuf C., Puchta R. and Schleyer P.v.R., Chem. Rev.,105, 3842 (2005).
- 17. a)Kruszewski J. andKrygowskiT.M., Tetrahedron Lett., 3842 (1972); b) Krygowski T.M., J. Chem. Inf.Comput. Sci., 33, 70 (1993); c) Krygowski T.M. and Cyrański M., in: Advances in Molecular Structure Research, Hargittai M., Hargittai L, (Eds.) JAI Press: London, 1997; d) Krygowski T.M. and Cyrański M.K., Chem. Rev., 101, 1385 (2001).
- 18. Krygowski T.M. and Cyranski M.K., Tetrahedron, 52, 1713 (1996).
- 19. a) Krygowski T.M., Anulewicz R. and Kruszewski J.,Acta Cryst. B, 39,732 (1983); b) Krygowski T.M.,Anulewicz R. and Wisiorowski M., PolishJ. Chem., 69,1579 (1995); c) Krygowski T.M., in: Structure and Reactivity, Liebman J.F., Greenberg A. (Eds.), VCH: Weinheim, 1988, chapt. 6, p. 231; d) Krygowski T.M., Progr. Phys. Org. Chem., 17, 239 (1991).
- 20. Krygowski T.M. and Stępień B.T., Polish J. Chem., 68,2213 (2004).
- 21. a) Nakata K., Fujio M., Saeki Y, Mishima M., Nishimoto K. and Tsuno Y, J. Phys. Org. Chem., 9, 561 (1996); b) Krygowski T.M., Stępień B.T., Cyrański M.K. and Ejsmont K., J. Phys. Org. Chem., 18, 886 (2005); c) Krygowski T.M., Dobrowolski M.A., Zborowski K. and Cyrański M.K., J. Phys. Org. Chem.,19, 889 (2006).
- 22. a) Krygowski T. M., J. Chem. Res. (S), 120 (1987); b) Exner O. and Bohm S., Curr. Organic Chem., 10,763 (2006).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0024-0156