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Molecular structure and effects of intermolecular hydrogen bonding on the vibrational spectrum of trifluorothymine, an antitumor and antiviral agent

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Abstract

In the present work, the experimental and the theoretical vibrational spectra of trifluorothymine were investigated. The FT-IR (400–4000 cm−1) and μ-Raman spectra (100–4000 cm−1) of trifluorothymine in the solid phase were recorded. The geometric parameters (bond lengths and bond angles) and vibrational frequencies of the title molecule in the ground state were calculated using ab initio Hartree–Fock (HF) method and density functional theory (B3LYP) method with the 6-31++G(d,p) and 6-311++G(d,p) basis sets for the first time. The optimized geometric parameters and the theoretical vibrational frequencies were found to be in good agreement with the corresponding experimental data and with results found in the literature. Vibrational frequencies were assigned based on the potential energy distribution using the VEDA 4 program. The dimeric form of trifluorothymine was also simulated to evaluate the effect of intermolecular hydrogen bonding on the vibrational frequencies. It was observed that the stretching modes shifted to lower frequencies, while the in-plane and out-of-plane bending modes shifted to higher frequencies due to the intermolecular N–H⋯O hydrogen bonds.

The optimized molecular structure of dimeric trifluorothymine.

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Acknowledgements

This work was supported by the research fund of Erzincan University (project no: 2011BAP-10.01.15). The computing resources used in this work were provided by the National Center for High Performance Computing of Turkey (UYBHM) under grant number 10812009. We also thank Assist. Prof. Dr. Hamit Mermerkaya for his assistance.

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  1. Department of Physics, Arts and Sciences Faculty, Erzincan University, 24100, Erzincan, Turkey

    Çağrı Çırak & Nurettin Koç

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  1. Çağrı Çırak
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Correspondence to Çağrı Çırak.

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Çırak, Ç., Koç, N. Molecular structure and effects of intermolecular hydrogen bonding on the vibrational spectrum of trifluorothymine, an antitumor and antiviral agent. J Mol Model 18, 4453–4464 (2012). https://doi.org/10.1007/s00894-012-1449-5

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