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

Abstract

KEYWORDSIn 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-(2methyl-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 E 2 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 1 H and 13 C 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.Vibrational spectra NBO analysis TD-DFT UV spectra NMR Metronidazole

Synthesis and structure investigation of novel pyrimidine-2,4,6-trione derivatives of highly potential biological activity as anti-diabetic agent

“…9. As can be seen from Table 6, there is good agreement between the experimental and calculated scaled IR vibrational frequencies [63].…”

Structural, spectral, thermodynamical, NLO, HOMO, LUMO and NBO analysis of fluconazole

“…Unassociated hydroxyl groups are absorbed strongly in the region3670-3580 cm -1 . Sirukarumbur Panduranga Vijaya Chamundeeswari et al, [47] observed a band at 3219 cm -1 in the IR spectrum as this ν O-H mode for2-(2-methyl-5-nitro-1-imidazolyl) ethanol. In 2,3-difluoro phenol [43], IR band observed at3372 cm −1 has been assigned to OH stretching vibration and comparison of those band with literature data predict that there is a deviation may be due to the fact that the presence of strong intramolecular hydrogen bonding.…”

“…The O-H in-plane bending vibration for phenol, in general, lies in the region 1150-1250 cm -1 and is not much affected due to hydrogen bonding unlike the stretching and out-of-plane bending wavenumber [49]. Sirukarumbur Panduranga VijayaChamundeeswari et al, [47] observed a band at 1265 and 1268 cm-1in the IR and Raman spectrum as this O-H inplane bending vibration mode for2-(2-methyl-5-nitro-1-imidazolyl) ethanol. In 2, 3-difluoro phenol [43], the medium IR band at1250 cm −1 has been assigned to OH in-plane bending vibration.…”

Spectral, thermal and kinetic studies of charge-transfer complexes formed between the highly effective antibiotic drug metronidazole and two types of acceptors: σ- and π-acceptors

“…(ii) C-H vibrations; it is easy to assign the C-H stretching vibration for the MZ donor because it has only one C-H stretching unit in the imidazole ring. The hetero aromatic structure of MZ shows the presence of C-H stretching vibration at 3100 cm -1 , which is the characteristic region for the ready identification of (C-H) [33]. (iii) CH 2 group vibrations; the C-H stretching vibrations of the methylene group are at lower frequencies than those of the aromatic C-H ring stretching.…”