Hydrogen bonding interaction between acrylic esters and monohydric alcohols in non-polar solvents: An FTIR study

Dharmalingam, K.; Ramachandran, K.; Sivagurunathan, Periyasamy

doi:10.1016/j.saa.2006.02.019

Cited by 39 publications

(27 citation statements)

References 17 publications

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“…[15][16][17][18][19][20] It is also noticed that the ν N-H stretching vibrations shift to high energy region and appear at 3475 and 3379 cm -1 suggesting the participation of NH 2 protons in host-guest interaction. …”

Section: Resultsmentioning

confidence: 90%

“…Figure 4 illustrates the 1 H NMR spectra of 1, 2d and 1:2d. FTIR spectroscopy analysis was performed also supported H-bonding interaction between 1 and 2d [15][16][17][18][19][20] (See experimental procedure). FTIR spectrum of 1 displays two sharp ν C=O stretching vibrations at 1726 and 1686 cm -1 due to the presence of methoxy ester carbonyls and two ν N-H stretching vibrations at 3457 and 3369 cm -1 which are characteristic for aromatic amines (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electron deficient nitroaromatics

Bayazit¹,

Coleman²

2014

Arkivoc

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Synthesis, characterization and the direct use of dimethyl 3-(4-aminophenyl)indolizine-1,2-dicarboxylate (1) as a photochemical sensor for the solution phase detection of nitroaromatics are presented. Fluorescent quenching experiments depict that nitroaromatics, particularly nitrophenol derivatives, may be probed by diester 1 with a detection limit of 6.66 × 10 -8 M. FTIR and 1 H NMR studies together with fluorescent spectral analysis suggest that H-bonding interaction between 1 and p-nitrophenol (2d) triggers the formation of ground-state complex (1:2d) which causes the fluorescent quenching via electron transfer from the HOMO of electron-rich indolizine to the LUMO of electron-deficient nitrophenolics through hydrogen bonding.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electron deficient nitroaromatics

Bayazit¹,

Coleman²

2014

Arkivoc

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“…It indicates the formation of a hydrogen bonding between –OH group of alcohol and C=O of coumarin. The relaxation time increases with the increase of bond length confirming the degree of cooperation, shape and size of the molecule [32]. …”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectroscopic, dielectric, molecular docking and DFT studies of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one: an anticancer agent

Beena

Sudha

Nataraj

et al. 2017

Chemistry Central Journal

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BackgroundCoumarin (2H-chromen-2-one) and its derivatives have a wide range of biological and pharmaceutical activities. They possess antitumor, anti-HIV, anticoagulant, antimicrobial, antioxidant, and anti-inflammatory activities. Synthesis and isolation of coumarins from different species have attracted the attention of medicinal chemists. Herein, we report the synthesis, molecular structure, dielectric, anticancer activity and docking studies with the potential target protein tankyrase.ResultsMolecular structure of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one (MBDC) is derived from quantum chemical calculations and compared with the experimental results. Intramolecular interactions, stabilization energies, and charge delocalization are calculated by NBO analysis. NLO property and dielectric quantities have also been determined. It indicates the formation of a hydrogen bonding between –OH group of alcohol and C=O of coumarin. The relaxation time increases with the increase of bond length confirming the degree of cooperation and depends upon the shape and size of the molecules. The molecule under study has shown good anticancer activity against MCF-7 and HT-29 cell lines. Molecular docking studies indicate that the MBDC binds with protein.ConclusionsIn this study, the compound (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one was synthesized and characterized by spectroscopic studies. The computed and experimental results of NMR study are tabulated. The dielectric relaxation studies show the existence of molecular interactions between MBDC and alcohol. Theoretical results of MBDC molecules provide the way to predict various binding sites through molecular modeling and these results also support that the chromen substitution is more active in the entire molecule. Molecular docking study shows that MBDC binds well in the active site of tankyrase and interact with the amino acid residues. These results are compared with the anti cancer drug molecule warfarin derivative. The results suggest that both molecules have comparable interactions and better docking scores. The results of the antiproliferative activity of MBDC and Warfarin derivative against MCF-7 breast cancer and HT-29 colon cancer cell lines at different concentrations exhibited significant cytotoxicity. The estimated half maximal inhibitory concentration (IC 50) value for MBDC and Warfarin derivative was 15.6 and 31.2 μg/ml, respectively. This enhanced cytotoxicity of MBDC in MCF-7 breast cancer and HT-29 colon cancer cell lines may be due to their efficient targeted binding and eventual uptake by the cells. Hence the compound MBDC may be considered as a drug molecule for cancer.Graphical abstractThe binding mode of the ligand MBDC at active site of protein and the graphical representation of cell inhibition for MCF-7 and HT-29 cell lines.

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“…Reports of alcohol/acrylic ester hydrogen bonding suggest that both monomer and alcohol structure impact the interactions. 39 Although t-butyl esters were not studied in these reports, it can be assumed that the increased steric hinderance from the bulky tertiary ester may disturb interactions between the propagating chain with MeOH. Polymerisation of tBuMA was noticeably slower, and its presence within the statistical copolymerisations extended reaction times and decreased second monomer conversion.…”

Section: Discussionmentioning

confidence: 99%

Exploring the homogeneous controlled radical polymerisation of hydrophobic monomers in anti-solvents for their polymers: RAFT and ATRP of various alkyl methacrylates in anhydrous methanol to high conversion and low dispersity

et al. 2015

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In previous reports, the use of anhydrous methanol in the homogeneous ATRP polymerisation of n-butyl methacrylate (nBuMA) was shown to yield polymers with dispersities as low as Ɖ = 1.02, despite methanol being widely regarded as an anti-solvent for p(nBuMA). Herein, we describe the homogeneous methanolic controlled radical polymerisation of three hydrophobic alkyl methacrylate monomers (methyl, t-butyl and n-butyl methacrylate) using both ATRP and RAFT to generate a range of homopolymers, statistical copolymers, amphiliphilic block copolymers and branched polymers. Methanolic ATRP and RAFT are compared, with RAFT able to target high degrees of polymerisation (800 monomer units) with very low dispersities (Ɖ = 1.06) in shorter reaction times (44 hrs) under these conditions. Poly(ethylene glycol)-derived macroinitiators were shown to generate well defined A-B and A-B-A block copolymers (Ɖ = 1.02-1.18) whilst branched A-B block copolymers with weight average molecular weights up to M w = 2.33x10 6 g/mol were readily synthesised. The role of methanol within the polymerisations is discussed.ATRP and RAFT of hydrophobic monomers in anhydrous methanol, a traditional precipitant for the polymers, has been shown to form homopolymers, branched copolymers and statistical copolymers from nBuMA, MMA and tBuMA at 60 °C and 25 °C to very high conversion, high molecular weight (DP n = 800 monomer units) and very low dispersities (as low as 1.02) without phase separation

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Hydrogen bonding interaction between acrylic esters and monohydric alcohols in non-polar solvents: An FTIR study

Cited by 39 publications

References 17 publications

Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electron deficient nitroaromatics

Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electron deficient nitroaromatics

Synthesis, spectroscopic, dielectric, molecular docking and DFT studies of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one: an anticancer agent

Exploring the homogeneous controlled radical polymerisation of hydrophobic monomers in anti-solvents for their polymers: RAFT and ATRP of various alkyl methacrylates in anhydrous methanol to high conversion and low dispersity

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