European Journal of Chemistry 2011, 2(2), 136-145 | doi: | Get rights and content

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Theoretical and experimental studies on 2-(2-methyl-5-nitro-1-imidazolyl)ethanol

Sirukarumbur Panduranga Vijaya Chamundeeswari (1) , Emmanuel Rajan James Jebaseelan Samuel (2) , Namadevan Sundaraganesan (3,*)

(1) Photonics Division, School of Advanced Sciences, Vellore Institute of Technology University, Vellore, 632014, Tamilnadu, India
(2) Photonics Division, School of Advanced Sciences, Vellore Institute of Technology University, Vellore, 632014, Tamilnadu, India
(3) Department of Engineering Physics, Annamalai University, Annamalai Nagar Chidambaram, 608002, India
(*) Corresponding Author

Received: 16 Jun 2010 | Accepted: 14 Nov 2010 | Published: 30 Jun 2011 | Issue Date: June 2011


In this work, we report a combined experimental and theoretical study on molecular structure, vibrational spectra, natural bond orbital (NBO) and UV spectral analysis of [2-(2-methyl-5-nitro-1-imidazolyl) ethanol] (Metronidazole-MTD). The FT-IR solid phase (4000-400 cm-1) liquid phase, and FT-Raman spectra (3500-50 cm-1) of MTD were recorded. The molecular geometry, harmonic vibrational frequencies and bonding features of MTD in the ground state have been calculated using the density functional method B3LYP with 6-311G(d,p) as basis set. The assignments of the vibrational spectra have been carried out with the help of the Gauss view program package. Stability of the molecule arising from hyperconjugative interactions and charge delocalization have been analyzed using natural bond orbital analysis. The results show that charge in electron density (ED) in the σ* and π* antibonding orbitals and second order stabilization energies E2 confirms the occurrence of Intramolecular Charge Transfer (ICT) within the molecule. The UV spectrum was measured in ethanol solution. The energy and oscillator strength calculated by Time-Dependent Density Functional Theory (TD-DFT) results complement the experimental findings. The calculated HOMO and LUMO energies show that charge transfer occurs within the molecule. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge Independent Atomic Orbital (GIAO) method and compared with experimental results.  Finally the results of calculations were applied to simulate Infrared and Raman spectra of the title compound which show good agreement with observed spectra.



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European Journal of Chemistry


Vibrational spectra; NBO analysis; TD-DFT; UV spectra; NMR; Metronidazole

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DOI: 10.5155/eurjchem.2.2.136-145.169

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How to cite

Vijaya Chamundeeswari, S.; Jebaseelan Samuel, E.; Sundaraganesan, N. Eur. J. Chem. 2011, 2(2), 136-145. doi:10.5155/eurjchem.2.2.136-145.169
Vijaya Chamundeeswari, S.; Jebaseelan Samuel, E.; Sundaraganesan, N. Theoretical and experimental studies on 2-(2-methyl-5-nitro-1-imidazolyl)ethanol. Eur. J. Chem. 2011, 2(2), 136-145. doi:10.5155/eurjchem.2.2.136-145.169
Vijaya Chamundeeswari, S., Jebaseelan Samuel, E., & Sundaraganesan, N. (2011). Theoretical and experimental studies on 2-(2-methyl-5-nitro-1-imidazolyl)ethanol. European Journal of Chemistry, 2(2), 136-145. doi:10.5155/eurjchem.2.2.136-145.169
Vijaya Chamundeeswari, Sirukarumbur, Emmanuel Rajan James Jebaseelan Samuel, & Namadevan Sundaraganesan. "Theoretical and experimental studies on 2-(2-methyl-5-nitro-1-imidazolyl)ethanol." European Journal of Chemistry [Online], 2.2 (2011): 136-145. Web. 3 Jun. 2023
Vijaya Chamundeeswari, Sirukarumbur, Jebaseelan Samuel, Emmanuel, AND Sundaraganesan, Namadevan. "Theoretical and experimental studies on 2-(2-methyl-5-nitro-1-imidazolyl)ethanol" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

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