Synthesis, Crystal Structure, Characterization and Ab Initio Calculations on a Dicycle Pyrazoline Derivative

• Autorzy: Guo H. M. , Zhang J. , Zhao P. S. , Jian F. F.
• Języki publikacji: EN

Abstrakty

EN

A dicycle pyrazoline derivative, 1-acetyl-5-(2-chlorophenyl)-3,4-(a-o-chlorotolylene-cyclohexano) pyrazoline, was synthesized and characterized by elemental analysis, IR, UV-Vis, fluorescence spectra and X-ray single crystal diffraction. Quantum chemical calculations were performed by using B3LYP and HF methods with 6-311G* basis set. Both methods can well simulate the molecular structure. Vibrational frequencies were predicted, assigned and compared with the experimental values, which suggest that both methods can only approximatively predict the vibrational frequencies. Electronic absorption spectra predicted by B3LYP/6-311G asterisk operator method well corresponding with the experimental data and natural bond orbital analyses indicate that the absorption bands are mainly derived from the contribution of n → pi asterisk operator and pi → pi asterisk operator transitions. For the system studied here, HF/6-311G asterisk operator method cannot be used to obtain the electronic absorption spectra. On the basis of vibrational analysis, the thermodynamic properties of the title compound at different temperature have been calculated, revealing the correlations between C0 p,m S 0 m, H0 m and temperature.

Słowa kluczowe

EN

crystal structure; vibrational frequency; electronic absorption spectra; fluorescence spectra; quantum chemical calculation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 2
• Strony: 263--274
• Opis fizyczny: Bibliogr. 28 poz., rys.

Twórcy

autor

Guo H. M.

autor

Zhang J.

autor

Zhao P. S.

autor

Jian F. F.

• Microscale Science Institute, Weifang College, Weifang Shandong 261061, P. R. China,

Bibliografia

• 1. Elguero J., ComprehensiveHeterocyclic Chemistryll, Katritzky A.R., Rees C. W. and Scriven E.F., Eds; Pergamon Press: Oxford, 1996; Vol. 3, p. 1.
• 2. Azarifar D. and Maleki B., J. Heterocycl Chem., 42, 157 (2005).
• 3. Levai A., J. Heterocycl. Chem., 39, l (2002).
• 4. Ramalingham K., Thyvekikakath G.X., Berlin K.D., Chesnut R.W., Brown R.A., Durham N.N., Ealick A.E. and van der Helm D., J. Med. Chem., 20, 847 (1977).
• 5. Brown R.E. and Shavrel Jr. J., Chem. Abstr., 76, 59618 (1972).
• 6. Lombardino J.G. and Otterness I.G., J. Med. Chem., 24, 830 (1981).
• 7. Fischer E. and Knövenagel O., Ann. Chem., 239, 194 (1887).
• 8. Levai A., ARKIVOC, ix, 344 (2005) and references therein.
• 9. Zhao P.S., Li Y.F., Guo H.M.,Wang X. and Jian F.F., Polish J. Chem., 81, 1735 (2007).
• 10. Zhao P.S., Li Y.F., Guo H.M., Jian F.F. and Wang, X., Bull. Korean Chem. Soc., 28, 1539 (2007).
• 11. Sheldrick G.M., SAINT v4 Software Reference Manual, Siemens Analytical X-ray System, Madison, WI, 1996.
• 12. Sheldrick G.M., SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Germany, 1996.
• 13. Sheldrick G.M., SHELXTL, v5 Reference Manual, Siemens Analytical X-Ray Systems: Madison, WI, 1997.
• 14. Wilson A.J., International Tables for X-Ray Crystallography, Kluwer Academic: Dordrecht, The Netherlands, 1992; Vol. C: Tables 6.1.1.4 (pp. 500-502) and 4.2.6.8 (pp. 219-222), respectively.
• 15. Dewar M.J.S., Zoebisch E.G. and Healy E.F., J. Am. Chem. Soc., 107, 3902 (1985).
• 16. Schlegel H.B., J. Comput. Chem., 3, 163 (1982).
• 17. Peng C., Ayala P.Y., Schiege J H.B. and Frisch M.J., J. Comput. Chem., 17, 49 (1996).
• 18. 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., Stefanoy 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.
• 19. Runge E. and Gross E.K.U., Phys. Rev. Lett., 52, 997 (1984).
• 20. Petersilka M., Gossmann U.J. and Gross E.K.U., Phys. Rev. Lett., 76, 1212 (1966).
• 21. Bauernschmitt R. and Ahlrichs R., Chem. Phys. Lett., 256, 1996 (1996).
• 22. Jamorski C., Casida M.E. and Salahub D.R., J. Chem. Phys., 104, 5134 (1996).
• 23. Foresman J.B., Head-Gordon M.J., Pople A. and Frisch M.J., J. Phys. Chem., 96, 135 (1992).
• 24. Hunter R.H., Haueisen R.H. and Irving A., Angew. Chem. Int. Ed. Engl., 33, 566 (1994).
• 25. Zhao P.S., Wang H.Y, Li R.Q. and Guo H.M., Indian J. Chem., A, 47, 986 (2008).
• 26. Zhao P.S., Guo H.M., Wang X. and Jian F.F., J. Chin. Chem. Soc., 55, 183 (2008).
• 27. Jian F.F., Zhao P.S., Yu Q., Wang Q.X. and Jiao K., J. Phys. Chem., A, 108, 5258 (2004).
• 28. Frish A., Nielsen A.B. and Holder A.J., Gaussview Users Manuał, Gaussian Inc, Pittsburgh, 2000.