Conformational analysis and vibrational study of daidzein by using FT-IR and FT-Raman spectroscopies and DFT calculations

Singh, Harsh; Singh, Swapnil; Srivastava, Anubha; Tandon, Poonam; Bharti, Purnima; Kumar, Sandeep; Maurya, Rakesh

doi:10.1016/j.saa.2013.10.045

Cited by 40 publications

(25 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, the *1260-1030 cm -1 range is assigned to the C-O stretching vibration. As far as Dai is concerned, according to a complete vibrational assignment already reported in literature [46], hydroxyl groups stretching modes are detected at *3214 cm -1 (shoulder) and *3151 cm -1 , indicative of the existence of hydrogen bonding between OH groups and neighbouring molecules, whereas the C-H stretching is observed at *3010 cm -1 (shoulder). The C=O stretching mode is detected at *1625 cm -1 , and an intense C=C stretching vibration is revealed at *1596 cm -1 , followed by a double peak at *1450, and *1379.6 cm -1 .…”

Section: Characterization In Solid Statementioning

confidence: 64%

Isoflavone aglycons-sulfobutyl ether-β-cyclodextrin inclusion complexes: in solution and solid state studies

Stancanelli

Venuti

Arigò

et al. 2015

J Incl Phenom Macrocycl Chem

View full text Add to dashboard Cite

The effect of a polyanionic variably substituted sulfobutyl ether-b-cyclodextrin (SBE-b-CyD), complexation on the UV absorption of genistein (Gen) and daidzein (Dai) was studied in pure water. A phase solubility study was performed, according to the method reported by Higuchi and Connors, to evaluate the changes of isoflavones in the complexation state and type-A L solubility diagrams for both isoflavones were obtained suggesting that they form complexes with 1:1 molar ratio. These results were confirmed by Job's plot method. Complexation strongly increases the water solubility of isoflavones. The in vitro dissolution of isoflavones entrapped into SBE-b-CyD significantly surpassed that of the free isoflavones (over 90 % of the loaded Gen and Dai dissolved in 15 and 30 min, respectively). Finally, 1:1 molar ratio solid complexes were prepared by the kneading method and characterized in solid state by FTIR-ATR spectroscopy, with particular regard to O-H and C=O stretching vibrations, achieving structural information on the modifications induced by complexation on the H-bond scheme, also by applying band decomposition and curve-fit.

show abstract

Section: Characterization In Solid Statementioning

confidence: 64%

Isoflavone aglycons-sulfobutyl ether-β-cyclodextrin inclusion complexes: in solution and solid state studies

Stancanelli

Venuti

Arigò

et al. 2015

J Incl Phenom Macrocycl Chem

View full text Add to dashboard Cite

show abstract

“…bands have been assigned carefully by comparing previous reports of similar kind of molecules. [6][7][8][9][10] The calculated scaled and unscaled wavenumbers of both the conformers and the corresponding observed peaks are tabulated in Table 1.…”

Section: Vibrational Assignmentsmentioning

confidence: 99%

“…[6][7][8][9][10] Here, we report on concise Fourier transform Raman (FT-Raman) and Fourier transform infrared (FT-IR) spectroscopic studies of the title molecule. Density functional theory (DFT) has become a beneficial tool to study the vibrational spectra of the complex molecules.…”

Section: Introductionmentioning

confidence: 99%

Conformational Study and Vibrational Spectroscopic (FT-IR and FT-Raman) Analysis of an Alkaloid-Borreverine Derivative

Singh

Karthick

et al. 2017

ANAL. SCI.

Self Cite

View full text Add to dashboard Cite

In the present work, structural and spectroscopic investigations were carried out on a borreverine derivative. Borreverine is a class of alkaloid as well a natural antimalarial drug extracted from Borreria verticillata. With the aim of finding possible conformers, a detailed conformational analysis of a borreverine derivative was conducted utilizing density functional theory employing the B3LYP/6-31G(d,p) method. The crystallographic geometry was used for full geometry optimization, followed by a conformational analysis. The conformational investigation predicted the most stable conformer (conformer I), which was further compared with the initial crystallographic geometry (conformer V). The geometry optimization, vibrational frequency, and intensity of these two conformers (I and V) were calculated in the ground state using density functional theory with the B3LYP functional and 6-31G(d,p) basis set. The spectroscopic investigation was conducted using Fourier transform infrared (FT-IR) and Fourier transform Raman (FT-Raman) techniques. Tentative vibrational assignments of some selective modes were presented utilizing the observed FT-IR, FT-Raman, and calculated spectra. The scaled and observed wavenumbers were found to be in good agreement. The molecular electrostatic potential was computed and plotted so as to elucidate the reactive sites of the molecule. Natural bond orbital studies were performed to investigate the intramolecular charge transfer that results in molecular stability.

show abstract

“…The population ratio among different conformers of the phenylacetyl chloride can be calculated based on their energies by using Boltzmann factor; [20] this is the simplest way of relating the energy differences to the population differences and can be expressed as exp(ÀE A /RT). [21] The population ratio of the conformers is shown in Table 1. From the table, it can be seen that the MP2 energies correspond to a population composition of 65% A and 35% B at room temperature, which is in fair agreement with the experimental results.…”

Section: Conformational Analysismentioning

confidence: 99%

“…The observed bands identified in Raman spectrum at 3063 and 3009 cm À1 and IR bands at 3066 and 3033 cm À1 were designated as C-H stretching vibrations of phenyl ring for both the conformers, which are further supported by the PED values. In substituted phenyl rings, the C-H in-plane and out-of-plane bending vibrations generally lie in the region 1500-1100 cm À1 and 1000-700 cm À1 , [21] …”

Section: C-h Vibrationsmentioning

confidence: 99%

Conformational stability and vibrational study of phenylacetyl chloride

Tao

Han

et al. 2015

J of Physical Organic Chem

View full text Add to dashboard Cite

The Fourier transform infrared spectroscopy and Fourier transform Raman spectra of phenylacetyl chloride were recorded and analyzed in the range 3500-400 and 3500-200 cm À1 at room temperature, respectively. In order to obtain the structural information and conformational stabilities, a potential energy surface scan for internal rotation was carried out at the B3LYP/6-31G(d) level. The potential energy surface reveals that the title compound has two minimal conformers (A and B). The optimized geometries, structural parameters, stabilities, energies, thermodynamic parameters, vibrational wavenumbers, infrared intensities, and Raman activities for the two conformers (A and B) have been obtained by employing B3LYP and MP2 calculations with 6-311++G (d, p) basis sets. The conformational energy difference between A and B is very small, indicating that the B conformer coexists with the A conformer. The detailed vibrational assignments of vibrational spectra of each conformer have been made on the basis of the potential energy distributions analysis. The highest occupied molecular orbitallowest unoccupied molecular orbital energy gap and molecular electrostatic potential of the two conformers have been also calculated for comparison of their chemical activities.

show abstract

Conformational analysis and vibrational study of daidzein by using FT-IR and FT-Raman spectroscopies and DFT calculations

Cited by 40 publications

References 69 publications

Isoflavone aglycons-sulfobutyl ether-β-cyclodextrin inclusion complexes: in solution and solid state studies

Isoflavone aglycons-sulfobutyl ether-β-cyclodextrin inclusion complexes: in solution and solid state studies

Conformational Study and Vibrational Spectroscopic (FT-IR and FT-Raman) Analysis of an Alkaloid-Borreverine Derivative

Conformational stability and vibrational study of phenylacetyl chloride

Contact Info

Product

Resources

About