Powiadomienia systemowe
- Sesja wygasła!
- Sesja wygasła!
Tytuł artykułu
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
Reported is the crystal structure of a formally symmetric bis(s-triazinyl) ether obtained as a by-product in the acylation reaction of less reactive nucleophiles with 2-acyloxy-4,6-dimethoxy-1,3,5-tri azines. The title ether shows conformational asymmetry evi - denced by different orientations of the four methoxy groups and the two aromatic rings in relation to the central etheric plane. Differentiation of the two O–C(triazine) bond lengths of the bis(triazinyl) ether can be correlated with the angles between s-triazine rings with the central etheric plane, indicating different degree of conjugation of the two pi-systems with alone pair of the central oxygen atom. It seems that primary reason for the observed asymmetry is crystal packing, causing different orientations of methoxy groups, which in turn induced bond lengths alternation in the s-triazine rings affecting their conjugations with central O atom through AGIBA effect. The experimental obser - vations are in agreement with ab in itio calculation.
Wydawca
Czasopismo
Rocznik
Tom
Strony
2163--2172
Opis fizyczny
Bibliogr. 28 poz., rys.
Twórcy
autor
autor
autor
autor
autor
- Institute of General and Ecological Chemistry Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland, marekglo@p.lodz.pl
Bibliografia
- 1. Kamiński Z.J., J. Prakt. Chem., 332, 579 (1990).
- 2. Sochacki M. and Kamiński Z.J., Org. Mass Spectrom., 29, 102 (1994).
- 3. Kamińska J.E., Kamiński Z.J. and Góra J., Synthesis, 593 (1999).
- 4. Kamiński Z.J., Kolesińska B., Kolesińska J., Sabatino G., Chelli M., Rovero R, Błaszczyk M., Główka M.L. and Papini A.M., J. Am. Chem. Soc., 127, 16912 (2005).
- 5. Speakman R.H., Chem. Ind., 232 (1977).
- 6. Sakurai R., Hashida Y. and Matsui K., Buli. Chem. Soc. Jpn., 51, 2175 (1978).
- 7. Vakhnatova G.M., Anisimova O.S. and Ihantov L.N., Khim. Geterotsikl. Soedin., 11, 1557 (1979).
- 8. Mikhailichenko S.N., Chesnyuk A.A., Konyushkin L.D. and Zaplishnyi V.N., Russ. Chem. Bull., Int. Ed, 52,2157(2003).
- 9. Sheldrick G.M., Acta Cryst., A64, 112 (2008).
- 10. Allen RH., CSD, Acta Cryst., B58, 380 (2002).
- 11. Bruno I.J., Cole J.C., Edgington P.R., Kessler M., Macrae C.R., McCabe P., Pearson J. and Taylor R., CONQUEST, Acta Cryst., B58, 389 (2002).
- 12. Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L., Taylor R., van de Streek J. and Wood P.A., MERCURY, J. Appl. Cryst., 41, 466 (2008).
- 13. VISTA- A Program for the Analysis and Display of Data Retrieved from the CSD. Cambridge Crystallography Data Centre, 12 Union Road, Cambridge, England, CDC (1994).
- 14. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S.J., Windus T.L., Dupuis M. and Montgomery J.A., GAMESS version 27 June 2005 (R5) from Iowa State University; J. Comput. Chem., 14, 1347 (1993).
- 15. Krishnan R., Binkley J.S., Seeger R. and Popie J.A., J. Chem. Phys., 72, 650 (1980).
- 16. Becke A.D., J. Chem. Phys., 98, 5648 (1993).
- 17. Stephens P.J., Devlin F.J., Chablowski C.F. and Frisch M.J., J. Phys. Chem., 98, 11623 (1994).
- 18. Hertwig R.H. and Koch W, Chem. Phys. Lett., 268, 345 (1997).
- 19. Główka M.L., Szczesio M. and Olczak A., 2009 in preparation.
- 20. Olczak A., private communication (2008).
- 21. Aakeroy C.B., Desper J. and Urbina J.F., CrystEngComm.,1, 193 (2005).
- 22. Klebe G., Struct. Chem., 1, 597 (1990).
- 23. Krygowski T.M., Wisiorowski M., Howard S.T. and Stolarczyk L.Z., Tetrahedron, 53, 13027 (1997).
- 24. Howard ST., Krygowski T.M., Ciesielski A. and Wisiorowski M., Tetrahedron, 54, 3533 (1998).
- 25. Krygowski T.M., Anulewicz R. and Kruszewski J., Acta Cryst., B39, 372 (1983).
- 26. Mrozek A. and Karolak-Wojciechowska J., Polish J. Chem., 81, 721 (2007).
- 27. Mrozek A., Karolak-Wojciechowska J., Amiel P. and Barbe J., J. Mol. Struct, 424, 151 (2000).
- 28. Mrozek A., Karolak-Wojciechowska L, Amiel P. and Barbe J., J. Mol. Struct., 424, 159 (2000).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ7-0016-0026