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Experimental and theoretical structural studies on 4-(2-phenylethyl)-5-(2-furyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

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Abstract

The structural and conformational features of 4-(2-phenylethyl)-5-(2-furyl)-2, 4-dihydro-3H-1,2,4-triazole-3-thione (1a), which can be related to the biological activity, have been investigated by X-ray diffraction and molecular modeling techniques. Ab initio method (RHF/6-31G) and density functional theory (B3LYP/6-31G(D)) have been used to calculate structural parameters, conformations, and relative energy of two tautomeric specious (1a and 1b) of the title compound. The geometry and the conformation of the thione form, 1a, is well reproduced by the DFT (B3LYP/6-31G(D)) method as compared with X-ray structure in which this form is found. The thione form is also predicted to be 14.42 kcal/mol more stable than the thiol form in the gas-phase by the DFT method.

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Acknowledgments

Financial support from the Research Foundation of Hacettepe University (Project number: 03 02 602 001) is gratefully acknowledged. The authors are deeply indebted to G. Çapan, who supplied the investigated compound.

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  1. Department of Physics Engineering, University of Hacettepe, 06800, Beytepe, Ankara, Turkey

    Arzu Karayel & Süheyla Özbey

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  1. Arzu Karayel
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  2. Süheyla Özbey
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Correspondence to Süheyla Özbey.

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Karayel, A., Özbey, S. Experimental and theoretical structural studies on 4-(2-phenylethyl)-5-(2-furyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione. Struct Chem 19, 391–397 (2008). https://doi.org/10.1007/s11224-008-9293-z

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  • DOI: https://doi.org/10.1007/s11224-008-9293-z

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