Analysis of vibratinal spectra of 8-hydroxyquinoline and its 5,7-dichloro, 5,7-dibromo, 5,7-diiodo and 5,7-dinitro derivatives based on density functional theory calculations

• Autorzy: Khaled Bahgat , Abdel Ragheb
• Języki publikacji: EN

Abstrakty

EN

The geometry, frequency and intensity of the vibrational bands of 8-hydroxyquinoline and its 5,7-dichloro, 5,7-dibromo, 5,7-diiodo and 5,7-dinitro derivatives were obtained by the density functional theory (DFT) calculations with Becke3-Lee-Parr (B3LYP) functional and 6-31G* basis set. The effects of chloride, bromide, iodide and nitro substituent on the vibrational frequencies of 8-hydroxyquinoline have been investigated. The assignments have been proposed with aid of the results of normal coordinate analysis. The observed and calculated spectra are found to be in good agreement. [...]

Słowa kluczowe

EN

DFT calculations; vibrational spectra; 8-hydroxyquinoline; 5,7-dichloro; 5,7-dibromo; 5,7-diiodo; 5,7-dinitro-hydroxyquinoline

• Czasopismo: Open Chemistry
• Rocznik: 2007
• Tom: 5
• Numer: 1
• Strony: 201-220

Daty

wydano

2007-03-01

online

2007-03-01

Twórcy

autor

Khaled Bahgat

• Chemistry Department, Faculty of Petroleum and Mining Engineering, Suez Canal University, Suez, Egypt,

autor

Abdel Ragheb

• Chemistry Department, Faculty of Petroleum and Mining Engineering, Suez Canal University, Suez, Egypt

Bibliografia

• [1] R.E. Bambury: Bnger’s Medicinal Chemistry Part II, John Wiley, New York, 1979, p. 41.
• [2] A. E. Martell and M. Calvin: Chemistry of the Metal Chelate Compounds, Prentice Hall, Englewood Cliffs, (1959).
• [3] S. Chabereck and A.E. Martell: Organic Sequestering Agents, Wiley, New York, NY, (1959).
• [4] V. Krishnakumar and R. Ramasay: ”DFT studiesand vibrational spectra of isoquinoline and 8-hydroxyquinoline”, Spectrochim. Acta A, Vol. 61, (2005), p. 673. http://dx.doi.org/10.1016/j.saa.2004.05.030[Crossref]
• [5] Kami Arici, Murat Yurdakul and Senay Yrdakul: “HF and DFT studies of the structure and vibrational spectra of 8-hydroxyquinoline and its mercury (II) halide complex”, Spectrochim. Acta A, Vol. 61, (2005), p. 37. http://dx.doi.org/10.1016/j.saa.2004.03.026[Crossref]
• [6] C.M. Cheatum, M.N. Heckscher and F.F. Crim: “Excited-state dynamics in 8-hydroxyquinoline dimmers”, Chem. Phys. Lett., Vol. 349, (2001), p. 37. http://dx.doi.org/10.1016/S0009-2614(01)01173-3[Crossref]
• [7] Q.S. Li, W.H. Fang: ”Theoretical studies of 8-hydroxyquinoline, Chem. Phys. Lett., Vol. 367, (2003), p. 673.
• [8] A. Ragheb, A. Shalabi, E. Sawi: ”Synthesis and characterization of hydroxyquinoline derivatives”, J. Serb. Chem. Soc., Vol. 52, (1987), pp. 697–703.
• [9] M.J. Frisch, G.W. Truchs, H.B. Schlegel, P.M. Johnson, M.A. robb, J.R. Cheeseman, T.A. Keith, G.A. Peterson, J.A. Montgomeri, M.A. Al-Laham, U.G. Zakrzewski, J.V. Ortiz, J.B. Fotesman, C.Y. Reng, P.Y. Ayala, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. defrees, J. Baker, J.P. Stewart, M. Head-Gardon, C. Gonzalea and A. Pople, gaussian94w (revision B. 3), gaussian, inc., pittsburgh, PA, 1995.
• [10] A.D. Beckee: ”Density-functional thermochemistry. III. The role of exact exchange”, J. Chem. Phys., Vol. 98, (1993), pp. 5648. http://dx.doi.org/10.1063/1.464913[Crossref]
• [11] C. Lee, W. Yang and R.G. Parr: “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B., Vol. 37, (1987), p. 785. http://dx.doi.org/10.1103/PhysRevB.37.785[Crossref]
• [12] P. Pulay, G. Fogarasi, G. pongor, J.E. Boggs and A. Vargha: “Combination of Theoretical ab Initio and Experimental Information to obtain reliable harmonic force constant. Scaled Quantum Mechanical Force Fields of Glyoxal, Acrolein, Butadiene, Formaldehyde and Ethylene”, J. Am. Chem. Soc., Vol. 105, (1985), p. 7037. http://dx.doi.org/10.1021/ja00362a005[Crossref]
• [13] G. Rauhut and P. Pulay: “Transferable Scaling Factors for Density Functional Derived Vibrational force Field”, J. Phys. Chem., Vol. 99, (1995), p. 3093. http://dx.doi.org/10.1021/j100010a019[Crossref]
• [14] G. Fogarasi, P. Pulay: Vibrational Spectra and Structure, Elsevier, Amsterdam, Vol. 14, 1985, pp. 125.
• [15] G. Fogarasi, X. Zhou, P.W. Taylor and P. Pulay: “The Calculation of ab initio molecular geometries: efficient optimization by natural internal coordinated and empirical correction by offset forces”, J. Am. Chem. Soc., Vol. 114, (1992), p. 8191. http://dx.doi.org/10.1021/ja00047a032[Crossref]
• [16] T. Sundius: “Molvib program for harmonic force fields by MOLVIB”, J. Mol. Struct., Vol. 218, (1990), p. 321. http://dx.doi.org/10.1016/0022-2860(90)80287-T[Crossref]
• [17] T. sundius: “Scaling of ab initio force fields by MOLVIB”, Vib. Spectrosc., Vol. 29, (2002), p. 89. http://dx.doi.org/10.1016/S0924-2031(01)00189-8[Crossref]
• [18] F.A. Cotton: Chemical Application of Group Theory, Wiley Interscience, New York, 1971.
• [19] P. Roychowdhury, B.N. Das and B.S. Basak: “Crystal and molecular structure of 8-hydroxyquinoline”, Acta Crystallogr., Vol. C43, (1978), p. 1047.
• [20] D.N. Sathyanarayana: Vibrational Spectroscopy Theory and Applications, 2nd ed., New Age international (P) Limited publishers, New Delhi, 2004.
• [21] J. Bellamy: The Infrared Spectra of Complex Molecules, Wiley, New York, 1975.
• [22] M.S. Soliman: “Normal coordinate and infrared band intensities of trichloronitromethane and trichloroacetate ions”, Spectrochim. Acta, Vol. 49A, (1993), p. 189.
• [23] G. Socrates: Infrared and Raman Characteristic Group frequencies, J. Wiley, Chichester, 2001.
• [24] J.K. Brown and N. Sheppard: “Infra-red spectroscopic studies of rotational isomerism. Part 3.-The n-propyl halides”, Trans. Faraday Soc., Vol. 50, (1954), p. 1164. http://dx.doi.org/10.1039/tf9545001164[Crossref]

Identyfikatory

DOI

10.2478/s11532-006-0061-x