Vibrational spectra and normal coordinate analysis of diazepam, phenytoin and phenobarbitone

Gunasekaran, S.; Kumar, R. Thilak; Ponnusamy, S.

doi:10.1016/j.saa.2006.01.037

Cited by 66 publications

(36 citation statements)

References 12 publications

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“…On the other hand, the same hydrogen bond is arranged in a helical chain pattern along the [010] direction designated as C(8) graph set. Infrared spectra Table 4 lists the wavenumbers of the most important vibrations for the studied complexes and free ligand together with the proposed assignment [16,17]. The spectra of (1) and (2) are very similar indicating the same structure of the complexes.…”

Section: Resultsmentioning

confidence: 97%

“…The absorption band related to the stretching vibrations m(C4=O) was observed at 1720 and 1723 cm -1 , for (1) and (2), respectively. The m(C2=O) and m(C4=O) vibrations in pht and other hydantoins cause the absorption observed in the range 1783-1779 cm -1 and 1740-1720 cm -1 , respectively [16][17][18]. The low intensities of these bands in (1) and (2) are probably caused by the hydrogen bond activities involving O1 and O2 carbonyl oxygen and OW1 atoms of the water molecules coordinated to the metal ion.…”

Section: Resultsmentioning

confidence: 98%

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Interaction of hydantoins with transition metal ions: synthesis, structural, spectroscopic, thermal and magnetic properties of [M(H2O)4(phenytoinate)2] M = Ni(II), Co(II)

et al. 2009

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Complexes of Ni(II) and Co(II) of the formulae [Ni(H 2 O) 4 (pht) 2 ] (1) and [Co(H 2 O) 4 (pht) 2 ]Á1,5NH 3 ÁH 2 O (2) (where pht = phenotoinate anion) were obtained and characterized physicochemically. [Ni(H 2 O) 4 (pht) 2 ](1) crystallizes in a monoclinic space group P2 1 /c; a = 11.7358(8), b = 11,1250(8), 11.4182(7) Å ; b = 97.076(5)°; V = 1479.41 Å 3 ; Z = 2. The environment around the nickel and cobalt ions can be described as a distorted octahedron. The metal ion was found to bind to four water molecules and two nitrogen atoms derived from two anions of the monodentate phenytoinate. Four intramolecular hydrogen bonds designated as S(6) graph set are found in one [Ni(H 2 O) 4 (pht) 2 ] (1) molecule. Two chain HB patterns, constructed by the [Ni(H 2 O) 4 (pht) 2 ] molecules extending along the c and b axes, respectively, have been observed. The cobalt complex precipitates with the additional solvent molecules: one and a half of ammonia and one water. The results document the preferential binding of hydantoins to the metal ions through N(3) atom.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 98%

Interaction of hydantoins with transition metal ions: synthesis, structural, spectroscopic, thermal and magnetic properties of [M(H2O)4(phenytoinate)2] M = Ni(II), Co(II)

et al. 2009

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“…In this region, the signal positions (cm À1 ) were the same for all recorded spectra, but the ratio of the signal intensities varied. Signals in this area had been assigned to the bending vibrations of the hydantoin ring (Gunasekaran et al, 2006). Because the bending vibration is a complex movement of three atoms involved, it was difficult to clarify the relationship between the Raman signal intensity, polarization direction, and atomic movement, even though the hydantoin ring was proved to be placed parallel to the (0 0 1) face by the crystal structural analysis (Figs.…”

Section: Relationship Between Crystal Faces and Raman Spectramentioning

confidence: 99%

Crystal face identification by Raman microscopy for assessment of crystal habit of a drug

Moriyama

Furuno

Yamakawa

2015

International Journal of Pharmaceutics

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“…For heterocyclic compounds containing an N-H group, an N-H stretching band is observed in the 3500-3000 cm -1 region, the position of which depends upon the degree of hydrogen bonding [35,36]. In the present work, the theoretical calculation indicates that the scaled frequency value at 3610 cm -1 is assigned to N-H stretching vibrations.…”

Section: N-h Group Vibrationmentioning

confidence: 56%

Synthesis, spectroscopic investigations and computational study of monomeric and dimeric structures of 2-methyl-4-quinolinol

et al. 2015

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The present study aimed to determine an efficient and solvent-free method to synthesize 2-methyl-4-quinolinol (2MQ, also known as 4-hydroxy-2-methylquinoline) and includes spectroscopic investigations and computational studies. Molecular geometry and vibrational wavenumbers of 2MQ were investigated using the density functional (DFT/B3LYP) method with 6-311??G(d,p) and 6-311??G(2d,p) basis sets. According to calculations, the keto form of 2MQ is more stable than the annual form, and the dimeric conformation is predicted to be more stable than the monomeric conformations. A detailed analysis of the nature of the hydrogen bonding, using topological parameters such as electronic charge density, Laplacian, kinetic and potential energy density evaluated at the bond critical point, is also presented. The 1 H nuclear magnetic resonance chemical shifts of the molecule were calculated by the GIAO method. The molecule orbital contributions were studied by using total (TDOS) and partial (PDOS) density of states. The UV-visible spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were investigated by the time-dependent DFT (TD-DFT) approach. The linear polarizability (a) and the first-order hyperpolarizability (b) values of the investigated molecule were computed using DFT quantum mechanical calculations. The results show that the 2MQ molecule may have a nonlinear optical comportment with non-zero values. The stability and charge delocalization of the molecule was studied by natural bond orbital analysis.Electronic supplementary material The online version of this article (

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Vibrational spectra and normal coordinate analysis of diazepam, phenytoin and phenobarbitone

Cited by 66 publications

References 12 publications

Interaction of hydantoins with transition metal ions: synthesis, structural, spectroscopic, thermal and magnetic properties of [M(H2O)4(phenytoinate)2] M = Ni(II), Co(II)

Interaction of hydantoins with transition metal ions: synthesis, structural, spectroscopic, thermal and magnetic properties of [M(H2O)4(phenytoinate)2] M = Ni(II), Co(II)

Crystal face identification by Raman microscopy for assessment of crystal habit of a drug

Synthesis, spectroscopic investigations and computational study of monomeric and dimeric structures of 2-methyl-4-quinolinol

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