Molecular structure and vibrational spectra of ibuprofen using density function theory calculations

Liu, Lekun; Gao, Hongwei

doi:10.1016/j.saa.2011.12.068

Cited by 24 publications

(13 citation statements)

References 30 publications

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“…14 The molecular structure and vibrational spectra of IBP using density function theory (DFT) calculations were studied. 15 As seen in this research, many by-products have been detected, and several plausible degradation pathways have been proposed. However, little information about the mechanisms of OH-induced degradation of IBP by AOPs was reported.…”

Section: Introductionmentioning

confidence: 67%

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OH-initiated AOPs degradation mechanism of ibuprofen in aqueous environments

et al. 2014

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As a common pharmaceutical and personal care product, ibuprofen (IBP) is regarded as an important pollutant in aqueous environments. In this paper, the OH-initiated advanced oxidation processes (AOPs) degradation mechanism and its subsequent reaction mechanism with IBP were studied at the M06-2x/6-311++G(2d, p)//M06-2x/6-31+G(d,p) level. The frontier electron density and bond dissociation energy were analyzed. In addition, profiles of the potential energy surface were constructed, and all the possible pathways were discussed. H-atom abstraction is the most important mechanism. The dominant products were IBAP, 2-[4-(1-hydroxyisobutyl)phenyl]propionic acid, and 1-(4-isobutylphenyl)-1-ethanol, which is in good agreement with the experimental results.

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Section: Introductionmentioning

confidence: 67%

“…The bond lengths and main bond angles are compared with crystal experimental values, since we have no experimental values in liquid. 15 The mean relative deviation of bond lengths is 1.78%. The results are consistent with their experimental values.…”

Section: Resultsmentioning

confidence: 97%

OH-initiated AOPs degradation mechanism of ibuprofen in aqueous environments

et al. 2014

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“…The FTIR spectra of IBU showed a single characteristic peak at 1711 cm −1 due to carbonyl (C=O) stretching and three characteristic peaks between 2800 and 3300 cm −1 corresponding to the aromatic benzene ring C–H stretching [23]. S244FP carriers showed a stronger intensity band from 1300 to 900 cm −1 due to Si–O stretching of the silanol group [24].…”

Section: Resultsmentioning

confidence: 99%

Investigating the Effects of Loading Factors on the In Vitro Pharmaceutical Performance of Mesoporous Materials as Drug Carriers for Ibuprofen

et al. 2017

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The aim of the study was to investigate the effects of the loading factors, i.e., the initial drug loading concentration and the ratio of the drug to carriers, on the in vitro pharmaceutical performance of drug-loaded mesoporous systems. Ibuprofen (IBU) was used as a model drug, and two non-ordered mesoporous materials of commercial silica Syloid® 244FP (S244FP) and Neusilin® US2 (NS2) were selected in the study. The IBU-loaded mesoporous samples were prepared by a solvent immersion method with a rotary evaporation drying technique and characterized by polarized light microscopy (PLM), Fourier transform infrared (FTIR) spectroscopy, X-ray powder diffraction (XRPD) and differential scanning calorimetry (DSC). Dissolution experiments were performed in simulated gastric media at 37 °C under non-sink conditions. The concentration of IBU in solution was determined by HPLC. The study showed that the dissolution rate of IBU can be improved significantly using the mesoporous S224FP carriers due to the conversion of crystalline IBU into the amorphous form. Both of the loading factors affected the IBU dissolution kinetics. Due to the molecular interaction between the IBU and NS2 carriers, the loading factors had little effects on the drug release kinetics with incomplete drug desorption recovery and insignificant dissolution enhancement. Care and extensive evaluation must therefore be taken when mesoporous materials are chosen as carrier delivery systems.

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“…Indeed, previous quantum-chemical calculations predict a large number of low-energy conformers. [10][11][12][13] On the other hand, the carboxylic acid group can function both as hydrogen donor and acceptor, which is a main structural motif in crystalline ibuprofen and which can be important for its function as an inhibitor. 14,15 Furthermore, ibuprofen is chiral, featuring a stereogenic center at the a-carbon site connecting the carboxyl group and the aromatic ring.…”

Section: Introductionmentioning

confidence: 99%

The shape of ibuprofen in the gas phase

Betz

Zinn

Schnell

2015

Phys. Chem. Chem. Phys.

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Ibuprofen's pain-relieving properties arise from its ability to physically block the active site of an enzyme, thus making its structural and conformational properties highly interesting. We here present a conformer-selective high-resolution broadband rotational spectroscopy study of gas-phase ibuprofen. The interpretation of the spectroscopic results is supported by quantum-chemical calculations. We identify four low-energy conformers that differ in the structural arrangement of the isobutyl moiety with respect to the remainder of the molecule. While the isobutyl group shows high structural flexibility - resulting in distinct low-energy conformers - the propanoic acid group favors a stable arrangement.

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Molecular structure and vibrational spectra of ibuprofen using density function theory calculations

Cited by 24 publications

References 30 publications

OH-initiated AOPs degradation mechanism of ibuprofen in aqueous environments

OH-initiated AOPs degradation mechanism of ibuprofen in aqueous environments

Investigating the Effects of Loading Factors on the In Vitro Pharmaceutical Performance of Mesoporous Materials as Drug Carriers for Ibuprofen

The shape of ibuprofen in the gas phase

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