Hydrogen bonding in 2-hydroxybenzoyl and 2-hydroxythiobenzoyl compounds: Spectroscopic characterization and spectroscopic bond strength sequences

Steinwender, E.; Mikenda, W.

doi:10.1007/bf01277629

Cited by 20 publications

(5 citation statements)

References 19 publications

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“…The HBA molecules can easily form intramolecular hydrogen bonds, but the bonds are fairly weak and easy to break. In contrast, the intramolecular hydrogen bond in SiO 2 ‐APTMS‐UVA is much stronger than in HBA . The mechanism can explain well the difference in UV absorption between SiO 2 ‐APTMS‐UVA, other nanoparticles and HBA; furthermore the difference in photostabilization between the LDPE/SiO 2 ‐APTMS‐UVA and other LDPE composites or PP/SiO 2 ‐APTMS‐UVA and other PP composites can also be explained, as shown in Fig.…”

Section: Resultsmentioning

confidence: 72%

Nanosilica‐immobilized UV absorber: synthesis and photostability of polyolefins

Liu

Gao

Han

et al. 2015

Polymer International

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A nanosilica-immobilized UV absorber (SiO 2 -APTMS-UVA) was prepared by the following methods: the fumed nanosilica was first modified with an aminosilane coupling agent 3-aminopropyltrimethoxysilane (APTMS) and then reacted with hydroxy-benzoyl chloride. Several measurements confirmed that the UV absorber was chemically immobilized on the surface of the nanosilica. SEM observation showed that SiO 2 -APTMS-UVA was homogeneously dispersed in the matrix of low density polyethylene (LDPE) and polypropylene (PP). The photo-degradation of the nanocomposites was evaluated by an accelerated aging test. It was found that the SiO 2 -APTMS-UVA has a great effect on preventing the degradation of LDPE or PP under UV exposure.

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Section: Resultsmentioning

confidence: 72%

Nanosilica‐immobilized UV absorber: synthesis and photostability of polyolefins

Liu

Gao

Han

et al. 2015

Polymer International

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“…Recently, we have reported spectroscopic and theoretical data relevant to the characterization of intramolecular hydrogen bonding in a series of 2-hydroxybenzoyl compounds. , These studies have shown that the experimentally observed sequence of ν(OH) stretching frequencies, which can be directly related to the sequence of hydrogen bond strengths, is reasonably well reproduced by quantum chemical calculations at moderate computational levels, such as HF/6-31(d,p) or B3LYP/6-31(d,p). On the basis of hydrogen bond distances and partial charges, the calculations provided a consistent interpretation of this sequence.…”

Section: Introductionmentioning

confidence: 96%

Molecular Geometries and Vibrational Spectra of Phenol, Benzaldehyde, and Salicylaldehyde: Experimental versus Quantum Chemical Data

1997

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Geometric and vibrational spectroscopic data (rotational constants, bond distances and angles, vibrational frequencies, IR intensities, and OH/OD isotope effects) of phenol, benzaldehyde, and salicylaldehyde as calculated at various levels of theory (HF/6-31G(d,p), HF/6-311++G(d,p), MP2/6-31G(d,p), B3P86/6-31G(d,p), BLYP/6-31G(d,p), B3LYP/6-31G(d,p), and B3LYP/6-311++G(d,p)) are reported. The theoretical results are discussed mainly in terms of comparisons with available experimental data. For geometric data (rotational constants and bond distances) the best agreement between theory and experiment is obtained at the MP2 and B3LYP levels. B3P86 calculated data are slightly worse, while HF and BLYP calculations yield distinctly too small and too large bond distances, respectively. B3LYP calculated vibrational spectroscopic data excellently agree with experimental IR spectra for phenol, phenol-OD, and benzaldehyde, and with minor restrictions, also for salicylaldehyde and salicylaldehyde-OD. Considering frequency sequences, IR intensities, and OH/OD isotope effects, reliable and consistent assignments are given. BLYP and B3P86 calculated vibrational spectroscopic data are slightly worse, whereas MP2 and HF calculations suffer from several shortcomings that are already known from calculations of smaller molecules, such as benzene.

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“…This becomes particularly apparent if a series of compounds, including widely differing types of carbonyl groups, is considered. Recently, from a survey of spectroscopic data characterizing the intramolecular hydrogen bonds in a number of 2-hydroxybenzoyl compounds, it has been attempted to relate the hydrogen bond strengths, as determined from ν(OH) IR frequencies or from δ(OH) proton shifts, to other experimental quantities . The only significant result emerging from this analysis was that the sequence of hydrogen bond strengths can roughly be related to the ν(CO) carbonyl frequencies of the corresponding simple benzoyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in 2-Hydroxybenzoyl Compounds: Infrared Spectra and Quantum Chemical Calculations

1996

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IR gas-phase and quantum chemical data that characterize the intramolecular hydrogen bonds in a series of 2-hydroxybenzoyl compounds (Ph(OH)(COY): Y = Cl, OH, SH, OCH3, SCH3, H, CH3, Ph, N(CH(CH3)CH2)2CH2, N(CH2CH2)2CH2, N(CH3)2, NHCH3, NH2, NHNH2) are reported and discussed. The sequences of ν(OH) and of ν(CO) frequencies calculated at HF/3-21G, HF/6-31G**, and B3LYP/6-31G** computational levels agree reasonably well with the corresponding experimental sequences. The consistency of the calculated data is demonstrated by exploiting several relations between calculated frequencies, force constants, and bond distances. It is shown that the sequence of hydrogen bond strengths, as defined either by ν(OH) frequency shifts or by R(O−H) bond distances, may qualitatively be interpreted in terms of two quantities, the R(H···O) hydrogen bond distances and the Q(O) oxygen partial charges, which characterize the intrinsic differences between the carbonyl groups.

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Hydrogen bonding in 2-hydroxybenzoyl and 2-hydroxythiobenzoyl compounds: Spectroscopic characterization and spectroscopic bond strength sequences

Abstract: Summary.A survey of IR and NMR spectroscopic data is given for 30 2-hydroxybenzoyl and 2-hydroxy-thiobenzoyl compounds, which are representative for various kinds of (thio)carbonyl groups ( C

Cited by 20 publications

References 19 publications

Nanosilica‐immobilized UV absorber: synthesis and photostability of polyolefins

Nanosilica‐immobilized UV absorber: synthesis and photostability of polyolefins

Molecular Geometries and Vibrational Spectra of Phenol, Benzaldehyde, and Salicylaldehyde: Experimental versus Quantum Chemical Data

Intramolecular Hydrogen Bonding in 2-Hydroxybenzoyl Compounds: Infrared Spectra and Quantum Chemical Calculations

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