Vibrational spectra and first-order molecular hyperpolarizabilities of p-hydroxybenzaldehyde dimer

Sajan, D.; Erdoğdu, Y.; Kuruvilla, Thomas; Joe, I. Hubert

doi:10.1016/j.molstruc.2010.08.003

Cited by 27 publications

(9 citation statements)

References 35 publications

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“…While other angles exhibit small alterations, the dihedral angles 2 and 3 , which are primarily responsible for the gauche and the anti orientation, are quite different in HPE, compared with 2PE. The stable conformer of HBA exhibits a planar structure according to the present study, which is in agreement with a recent study (Sajan et al, 2010) based on the B3LYP/6-311++G(d,p) model. In Table 1 the calculated ring perimeter (R 6 ) (Wang et al, 2005) and bond angles of HBA exhibit good agreement with the crystal structure (Dickinson et al, 1997), and simulated dihedral angles of this study exhibit the planar shape of the molecule, which also agrees with the previous calculation (Sajan et al, 2010).…”

Section: Geometric Properties and Charge Distributionssupporting

confidence: 93%

Valence structures of aromatic bioactive compounds: a combined theoretical and experimental study

Arachchilage

Feyer

Plekan

et al. 2012

J Synchrotron Radiat

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Valence electronic structures of three recently isolated aryl bioactive compounds, namely 2-phenylethanol (2PE), p-hydroxyphenylethanol (HPE) and 4-hydroxybenzaldehyde (HBA), are studied using a combined theoretical and experimental method. Density functional theory-based calculations indicate that the side chains cause electron charge redistribution and therefore influence the aromaticity of the benzene derivatives. The simulated IR spectra further reveal features induced by the side chains. Solvent effects on the IR spectra are simulated using the polarizable continuum model, which exhibits enhancement of the O-H stretch vibrations with significant red-shift of 464 cm À1 in 2PE. A significant spectral peak splitting of 94 cm À1 between O(4)-H and O(8)-H of HPE is revealed in an aqueous environment. Experimental measurements for valence binding energy spectra for 2PE, HPE and HBA are presented and analyzed using outer-valence Green function calculations. The experimental (predicted) first ionization energies are measured as 9.19 (8.79), 8.47 (8.27) and 8.97 (8.82) eV for 2PE, HPE and HBA, respectively. The frontier orbitals (highest occupied molecular orbitals, HOMOs, and lowest unoccupied molecular orbitals, LUMOs) have similar atomic orbital characters although the HOMO-LUMO energy gaps are quite different.

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Section: Geometric Properties and Charge Distributionssupporting

confidence: 93%

Valence structures of aromatic bioactive compounds: a combined theoretical and experimental study

Arachchilage

Feyer

Plekan

et al. 2012

J Synchrotron Radiat

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“…The O–H stretching region of vanillin (4-hydroxy-3-methoxybenzaldehyde), with a wide signal between 3800 cm −1 and 2000 cm −1 , is characteristic of some spectra when obtained in solid phase in KBr pellets. 24–26 This band undergoes a change after formation of the inclusion complex with amylose similar to that observed by Rajendiran and Balasubramanian 24 when comparing the spectrum of pure vanillin with the spectrum of the sample of the inclusion complex with β-cyclodextrin as host. The observed change suggests a close interaction of the OH phenolic group with the amylose in the complex, leading to a noticeable shift to higher frequencies and a decrease in band width; still a faint shoulder can be seen at 3260 cm −1 overlapped by the O–H stretching band of the starch, which in fact also shifted from 3350 to 3415 cm −1 .…”

Section: Discussionsupporting

confidence: 77%

Host–Guest Molecular Interactions in Vanillin/Amylose Inclusion Complexes

Rodríguez

Bernik

2013

Appl Spectrosc

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18 19The interaction of 4-hydroxy-3-methoxybenzaldehyde (vanillin) and Hylon VII 20 due to the formation of an inclusion complex is studied by Fourier transformed infrared 21 spectroscopy (FTIR), differential scanning calorimetry (DSC) and circular dichroism 22 (CD). The results confirm the close interaction among the different functional groups of 23 vanillin and its host. In addition, a second case study was carried out with an amylose 24 from a different source (100% amylose, APTIII). As a result, remarkable differences 25 were found in the vanillin complexation capability of this amylose, which is only 26 evidenced in solution by circular dichroism spectroscopy studies through a clear Cotton 27effect. This finding confirm the value of using CD studies, which allow finding that, 28 depending of the amylose source, inclusion complexes can be found only in

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“…The O―H vibrations are extremely sensitive to formation of hydrogen bonding . The hydroxyl group which does not form hydrogen bond can strongly in the 3700 to 3584 cm −1 region, while the existence of intermolecular hydrogen bond formation can lower the O―H stretching wavenumber to the 3550 to 3200 cm −1 region .…”

Section: Resultsmentioning

confidence: 99%

Investigations on the structural, vibrational, computational, and molecular docking studies on potential antidiabetic chemical agent Diosmetin

Angamuthu

Ramachandrane²

2019

J of Molecular Recognition

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In the present study, the harmonic vibrational frequencies of Diosmetin(5, 7 dihydroxy-2(3-hydroxy-4 methoxyphenyl) chromen-4-one) have been investigated by both experimental (FTIR and FT-Raman) and theoretical (HF and DFT/B3LYP) method. The calculated harmonic vibrational frequencies were compared with experimental data. A detailed interpretation of the vibrational spectra of the compound has been made on the basis of the calculated potential energy distribution (PED). The 1 H, 13 C NMR chemical shifts and TD-DFT calculations of the molecule were calculated and compared with the available experimental observations. A study on the molecular electrostatic potential surface (MEP) of the compound was performed, and the electrophilic and nucleophilic reactive sites were identified. Furthermore, the inhibition effect of compound against aldose reductase enzyme has been analyzed by molecular docking method, and the results were compared with the standard drug. The docking study indicates that the investigated compound shows better inhibitory activity toward aldose reductase enzyme than the standard drug, and hence this study may be supportive in the field of drug discovery to design more potential antidiabetic agents.

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Vibrational spectra and first-order molecular hyperpolarizabilities of p-hydroxybenzaldehyde dimer

Cited by 27 publications

References 35 publications

Valence structures of aromatic bioactive compounds: a combined theoretical and experimental study

Valence structures of aromatic bioactive compounds: a combined theoretical and experimental study

Host–Guest Molecular Interactions in Vanillin/Amylose Inclusion Complexes

Investigations on the structural, vibrational, computational, and molecular docking studies on potential antidiabetic chemical agent Diosmetin

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