HOMA Model Extension for the Compounds Containing the Carbon-Selenium Bond

• Autorzy: Zborowski K. K. , Proniewicz L. M.
• Języki publikacji: EN

Abstrakty

EN

The HOMA (Harmonic Oscillator Model of Aromaticity) index is one of the most useful and popular calculation methods in the p-electron delocalization studies. Its idea is simple and calculations are very fast. Nevertheless, the HOMA method has not been applied so far to the compounds containing the carbon-selenium bond(s). In this work the HOMA parameters for such compounds are presented and several model selenium compounds are investigated. In order to obtain the deeper insight, calculations have been executed for oxygen and thio analogs of studied selenium compounds. HOMA values have been compared with the data provided by other aromaticity indices like IA, NICS(0) and NICS(1).

Słowa kluczowe

EN

aromaticity; heteroaromaticity; HOMA model; selenium compounds

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 3
• Strony: 477--484
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Zborowski K. K.

autor

Proniewicz L. M.

• Faculty of Chemistry, Jagiellonian University, 3 Ingardena Str., 30-060 Kraków, Poland ; tel.: [phone]/ext. 2067; fax: [phone],

Bibliografia

• l. Krygowski T.M., Cyranski M.K., Czarnooki Z., Hafelinger G. and Katritzky A.R., Tetrahedron, 56, 1783 (2000).
• 2. Krygowski T.M. and Cyranski M.K., Chem. Rev., 101, 1385 (2001).
• 3. Kruszewski J. and Krygowski T.M., Tetrahedron Len., 13, 3839 (1972).
• 4. Krygowski T.M., J. Chem. Inf. Comput. Sci., 33, 70 (1993).
• 5. Madura D., Krygowski T.M. and Cyranski M.K., Tetrahedron, 54, 14913 (1998).
• 6. Schleyer P. v R., Marker C., Dransfeld A., Jiao H.J. and Hommes N.J.R.Y., J. Am. Chem. Soc.,118,6317(1996).
• 7. Schleyer R v R., Manoharan M., Wang Z.X., Kiran B., Jiao H.J., Puchta R. and Hommes N.J.R.Y., Org. Lett.,3,2465(2001).
• 8. Bird C.W., Tetrahedron, 41, 1409 (1985).
• 9. Gordy W., J. Phys. Chem., 15, 305 (1947).
• 10. Bird C.W., Tetrahedron, 42, 89 (1986)
• 11. Becke A.D., J. Chem. Phys., 98, 5648 (1993).
• 12. Krishnan R., Binkley J.S., Seeger R. and Pople J.A., J. Chem. Phys., 72, 650 (1980).
• 13. Wolinski K. Hilton J.F. and Pulay R, J. Am. Chem. Soc., 112, 8251 (1990).
• 14. Gaussian 03, Revision C.02, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T, Kudin K.N., Burant J.C., Millam J.M., Iyengar 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., Bakken B.V., Adamo C., Jaramillo J., Gomperts J.R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.A., 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 R., Komaromi L, Martin R.L., Fox D.J., Keith T, Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gili RM.W., Johnson B., Chen W., Wong M.W., Gonzalez C. and Pople J.A.; Gaussian, Inc., Wallingford CT (2004).
• 15. Barrow R.F., Long D.A. and Millen D.J., Molecular Spectroscopy, The Chemical Society, Burlington House, London, 1975, vol. 3.
• 16. Brown R.D., Godfrey P.D., McNaughton D. and Taylor P.R., J. Mol. Spectr., 120, 292 (1986).
• 17. Katritzky A.R., Barczynski R, Musumurra G., Pisano D. and Szafran M., J. Am. Chem. Soc., 111, 7 (1989).
• 18. Jug K. and Koester A., J. Phys. Org. Chem., 4, 163 (1991).
• 19. Cyranski M.K. and Krygowski T.M., Polish J. Chem., 69, 1088 (1995).
• 20. Krygowski T.M. and Cyranski M.K., Tetrahedron, 52, 1713 (1996).
• 21. Pauling L., J. Am. Chem. Soc, 69, 542 (1947).
• 22. Krygowski T.M. and Cyranski M.K., Tetrahedron, 52,10255 (1996).
• 23. Cyranski M.K., Krygowski T.M., Katritzky A.R. and Schleyer P.V.R., J. Org. Chem., 67,1333 (2002).