Three antipyrine derivatives of o-, m- and p-chlorobenzylideneaminoantipyrines were characterized by spectral techniques and density functional calculations. The optimized configurations are very close to the XRD values and are used as foundations to investigate the molecular properties. The spectral assignments were attempted to ascribe to the vibrational modes of the detailed substructures with the aid of theoretical calculations because of the satisfactory consistencies between the experimental and theoretical spectra for each of the studied compounds. Raman spectral ascriptions represent that the pi-conjugated moieties linked by Schiff base imines are responsible for the excellent Raman scattering activities of these compounds. The linear polarizabilities and first hyperpolarizabilities of the studied molecules indicate that the compounds are good candidates of nonlinear optical materials. The statistical thermodynamic functions and their correlations with temperatures obtained from the theoretical vibrations are similar to each other among the isomers.
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