Potential energy profile, structural, vibrational and reactivity descriptors of trans–2–methoxycinnamic acid by FTIR, FT-Raman and quantum chemical studies

Arjunan, V.; Anitha, R.; Thenmozhi, S.; Marchewka, M.K.; Mohan, S.

doi:10.1016/j.molstruc.2016.02.034

Cited by 21 publications

(10 citation statements)

References 53 publications

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“…The out of plane bending vibrations of the compound are observed in the low frequency region. The results are in good agreement with the literature values [27,28].…”

Section: C-h Vibrationssupporting

confidence: 92%

“…The shifting in vibrational frequencies is higher due to the high electro negativity of chlorine atom attached to the carbonyl group. The inductive effect of chlorine attract electrons from the C=O bond, which increases the force constant and leads to an increase in the absorption frequency [28,29]. CF3 vibrations: The trifluoromethyl group has seven fundamentals frequencies, CF3 group attached to an aromatic carbon absorbs strongly in the region 1360-1090 cm -1 [30].…”

Section: C-h Vibrationsmentioning

confidence: 99%

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Structure, Vibrations, Molecular Orbitals, Reactivity Properties of 3-Trifluoromethylphenylchloroformate by FT-IR, FT-Raman, FT-NMR and DFT Studies

Arjunan

Senthilkumari

Mohan³

2019

Asian J. Chem.

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Due to the high electronegativity and small size of fluorine, the replacement of hydrogen atoms by fluorine in organic compounds often results in the profound change in their physical and chemical properties, including the stability, high lipophilicity and bioavailability [1-3]. Organo fluorine compounds have found broad applications in both life science and material sciences. Around 20 % of all pharmaceuticals and 30-40 % of all agrochemicals on the market contain fluorine [4,5]. Nucleophilic and perfluoroalkylation using organometallic compounds of lithium, magnesium and zinc has been vastly studied [6]. Chloroformates are useful catalysts for the polymerization of unsaturated compounds and in the preparation of polycarbonates, polyesters and formaldehyde polymers. Chloroformates are used as intermediates in the synthesis of pesticides, herbicides, perfumes, pharmaceuticals, foods, polymers and dyes. Chloroformates are also used for conversion to peroxydicarbo

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“…The out of plane bending vibrations of the compound are observed in the low frequency region. The results are in good agreement with the literature values [27,28].…”

Section: C-h Vibrationssupporting

confidence: 92%

Section: C-h Vibrationsmentioning

confidence: 99%

Structure, Vibrations, Molecular Orbitals, Reactivity Properties of 3-Trifluoromethylphenylchloroformate by FT-IR, FT-Raman, FT-NMR and DFT Studies

Arjunan

Senthilkumari

Mohan³

2019

Asian J. Chem.

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“…These results may appear unexpected, as, in the previous literature, on the basis of hybrid-DFT calculations, OMC trans isomers (with respect to the C3=C4 double bond) are quoted to be more stable than the cis ones in both gas and solution phases . 48,50,76 On the other hand, the higher stability of Trans2 with respect to Trans1 is not surprising, as the…”

Section: Resultsmentioning

confidence: 97%

A Post-HF Approach to the Sunscreen Octyl Methoxycinnamate

Fois¹,

Oriani²,

Tabacchi

2021

Preprint

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Octyl methoxycinnamate (OMC) is a commercial sunscreen with excellent UVB filter properties. However, it is known to undergo a series of photodegradation processes that decrease its effectiveness as UVB filter. In particular, the trans (E) form - which is considered so far the most stable isomer - converts to the cis (Z) form under the effect of light. In this work, by using post-Hartree-Fock approaches (CCSD, CCSD(t) and CCSD+T(CCSD)) on ground state OMC geometries optimized at the MP2 level we show that the cis and trans form of the gas-phase OMC molecule have comparable stability. Our results suggest that the cis form is stabilized by intra-molecular dispersion interactions, leading to a folded, more compact structure than the trans isomer.<br>

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“…(2a) and 2000-400 cm -1 Fig. (2b) and the vibration assignments were described in Table 2 followed the literatures [30,31]. ) 1248 vs 1246 m βC-C-C 515 m a ν-stretching; β-in-plane bending; δ-deformation; ρ-rocking; γ-out-of-plane bending; ω-wagging.…”

Section: Characterization Of 4-ethoxy-cinnamic Acidmentioning

confidence: 82%

Effect oF β-Alanine on The Preparation of 4-Ethoxy-Cinnamic Acid

Hoài¹,

Ngoc²,

Nam³

et al. 2018

TOMSJ

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Objective: Cinnamic acid and its derivatives have a numerous potential applications in many different fields such as pharmacy, organic “building blocks”, and corrosion inhibitors. Method: It is well-known that Verley-Doebner modification is a high efficient method for the preparation of cinnamic acid derivaties, especially with the compounds containing electron-donating subtituents at para position in aromatic ring. In this paper, 4-ethoxy-cinnamic acid was synthesized according to Verley-Doebner reaction with the use of pyrine acting as catalyst and solvent. The effect of the β-alanine concentration on the conversion of the starting material of 4-ethoxy-benzaldehyde was thoroughly investigated using high performance liquid chromatography. The results showed that consuming of 8% of β-alanine would convert 100% of 4-ethoxy-benzaldehyde to 4-ethoxy-cinnamic acid. Result: The structure of the obtained 4-ethoxy-cinnamic acid was also confirmed using Fourier transform infrared spectroscopy, Raman spectroscopy, and Gas chromatography-Mass spectroscopy. Cinnamic acid and its derivatives have numerous potential applications in many different fields such as pharmacy, organic “building blocks”, and corrosion inhibitors. It is well-known that Verley-Doebner modification is a high efficient method for the preparation of cinnamic acid derivaties, especially with the compounds containing electron-donating subtituents at para position in aromatic ring. In this paper, 4-ethoxy-cinnamic acid was synthesized according to Verley-Doebner reaction with the use of pyrine acting as catalyst and solvent. The effect of the β-alanine concentration on the conversion of the starting material of 4-ethoxy-benzaldehyde was thoroughly investigated using high performance liquid chromatography. The results showed that consuming 8% of β-alanine would convert 100% of 4-ethoxy-benzaldehyde to 4-ethoxy-cinnamic acid. The structure of the obtained 4-ethoxy-cinnamic acid was also confirmed using Fourier transform infrared spectroscopy, Raman spectroscopy, and Gas chromatography-Mass spectroscopy.

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Potential energy profile, structural, vibrational and reactivity descriptors of trans–2–methoxycinnamic acid by FTIR, FT-Raman and quantum chemical studies

Cited by 21 publications

References 53 publications

Structure, Vibrations, Molecular Orbitals, Reactivity Properties of 3-Trifluoromethylphenylchloroformate by FT-IR, FT-Raman, FT-NMR and DFT Studies

Structure, Vibrations, Molecular Orbitals, Reactivity Properties of 3-Trifluoromethylphenylchloroformate by FT-IR, FT-Raman, FT-NMR and DFT Studies

A Post-HF Approach to the Sunscreen Octyl Methoxycinnamate

Effect oF β-Alanine on The Preparation of 4-Ethoxy-Cinnamic Acid

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