Experimental (FT-IR, FT-Raman, 1H, 13C NMR) and theoretical study of alkali metal 2-aminobenzoates

Samsonowicz, M.; Świsłocka, Renata; Regulska, E.; Lewandowski, W.

doi:10.1016/j.molstruc.2007.11.041

Cited by 12 publications

(5 citation statements)

References 14 publications

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“…FT-IR, FT-Raman, 1 H and 13 C NMR measurements as well as quantum chemical calculations were used in this research. The present work is a continuation of the recent reports [2,[5][6][7].…”

Section: Introductionsupporting

confidence: 60%

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Comparison of molecular structure of alkali metal ortho substituted benzoates

Świsłocka

2010

Spectroscopy

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Abstract. The influence of the amino-, nitro-, methoxy-, hydroxy-and chloro-substituents in the ortho position towards the carboxylic group as well as alkali metal on molecular structure of benzoates was estimated. Optimized geometrical structures were calculated by B3LYP/6-311++G** method. Experimental FT-IR, FT-Raman and NMR spectra of the title compounds were recorded and analyzed. Data of chemical shifts in 1 H and 13 C NMR as well as wavenumbers and intensities in IR and Raman spectra of studied benzoate derivatives were analyzed in comparison with benzoic acid and with alkali metal benzoates.

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“…FT-IR, FT-Raman, 1 H and 13 C NMR measurements as well as quantum chemical calculations were used in this research. The present work is a continuation of the recent reports [2,[5][6][7].…”

Section: Introductionsupporting

confidence: 60%

“…The alkali metal benzoates substituted in ortho position were prepared as described in the literature [2,[5][6][7]. The IR spectra were recorded with the EQUINOX 55, BRUKER FT-IR spectrometer within the range 4000-400 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Comparison of molecular structure of alkali metal ortho substituted benzoates

Świsłocka

2010

Spectroscopy

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“…The chemical shifts of protons ( 1 H NMR) and carbons ( 13 C NMR) in the series of alkali metal coumarates express the influence of studied metal cations on the electronic charge distribution around carbon and hydrogen atoms [12]. One may observe a decrease in chemical shifts in case of all protons in comparison to appropriate shifts in the spectra of ligand (Fig.…”

Section: Nmr Spectramentioning

confidence: 99%

“…Replacement of the carboxylic group hydrogen with a metal ion brought about characteristic changes in the IR and Raman spectra of the metal p-coumarates in comparison with the spectra of ligand [12]. One can observe disappearance of bands of the symmetric and asymmetric valence vibrations: stretching ν(C=O) at 1672 (IR) cm −1 , β(C=O) at 692 (IR) and 680 cm −1 (Raman), as well as γ(C=O) at 557 (IR) and 552 cm −1 (Raman) of the carbonyl group; disappearance of stretching vibrations ν(O-H) at 2839 cm −1 (IR) and deformation vibrations β (O-H); appearance of bands of the asymmetric and symmetric vibrations of the carboxylate anion ν as (COO − ), ν s (COO − ), as well as β as (COO − ), β s (COO − ), and disappearance or changes in positions and intensities of some aromatic bands.…”

Section: Ft-ir and Ft-raman Spectramentioning

confidence: 99%

Spectroscopic (FT-IR, FT-Raman,¹H and¹³C NMR) and theoretical studies ofp-coumaric acid and alkali metalp-coumarates

et al. 2012

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The evaluation of the electronic charge distribution in metal complexes enables more precise interpretation of mechanism by which particular metal ions affect biochemical properties of ligands [J. Inorg. Biochem. 99 (2005), 1407–1423, J. Mol. Struct. 919 (2009), 284–289]. In this paper we investigated the influence of alkali metal cations (lithium, sodium, potassium, rubidium and cesium) on the electronic structure ofp-coumaric acid (p-CA). It allowed to observe the systematic changes in the spectra of investigated complexes depending on the position of the element in the periodic table.p-Coumaric acid is a derivative of cinnamic acid that occurs in several plant species. Li, Na, K, Rb and Csp-coumarates were synthesized and the experimental and theoretical FT-IR, FT-Raman,1H and13C NMR spectra ofp-coumaric acid and its salts were registered and analyzed. The structures, atomic charges, infrared and NMR spectra ofp-coumaric acid and Li, Na, K salts were calculated by B3LYP/6-311++G**method.

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“…Data concerning the molecular structure of rosmarinic acid [7,8] and its antioxidant activity [9,10] are also available, but there is no information about alkali metal rosmarinates. The influence of metal ions on the structure parameters as well as some physical, chemical, and biological properties of biological active molecules were previously studied by our team [15,16,17,18].…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure and Antioxidant Properties of Alkali Metal Salts of Rosmarinic Acid. Experimental and DFT Studies

et al. 2019

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The molecular structure of alkali metal rosmarinates was studied in comparison to rosmarinic acid using FT-IR, FT-Raman, 1H and 13C NMR spectroscopy, as well as density functional theory (DFT) calculations. The B3LYP/6-311+G(d,p) method was used to calculate optimized geometrical structures of studied compounds, atomic charges, dipole moments, energies, as well as the wavenumbers and intensities of the bands in vibrational and NMR spectra. Theoretical parameters were compared to experimental data. Antioxidant activity was determined using two spectrophotometric methods: (i) Assessing the ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable radical and (ii) assay of antioxidant power of ferric ions reducing (FRAP). The linear correlations were found between HOMO–LUMO (highest occupied molecular orbital–lowest unoccupied molecular orbital) energy gap and the reducing power expressed as FRAP (R = 0.77) as well as between IC50 values (the ability of quenching DPPH radicals) and Δνas-s(COO) in IR spectra (differences between asymmetric and symmetric stretching vibrations bands) (R = 0.99). Photochemical properties of studied compounds were also evaluated. The influence of alkali metal on the electronic system of the rosmarinic acid molecule was discussed.

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Experimental (FT-IR, FT-Raman, 1H, 13C NMR) and theoretical study of alkali metal 2-aminobenzoates

Cited by 12 publications

References 14 publications

Comparison of molecular structure of alkali metal ortho substituted benzoates

Comparison of molecular structure of alkali metal ortho substituted benzoates

Spectroscopic (FT-IR, FT-Raman,¹H and¹³C NMR) and theoretical studies ofp-coumaric acid and alkali metalp-coumarates

Molecular Structure and Antioxidant Properties of Alkali Metal Salts of Rosmarinic Acid. Experimental and DFT Studies

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Experimental (FT-IR, FT-Raman, 1H, 13C NMR) and theoretical study of alkali metal 2-aminobenzoates

Cited by 12 publications

References 14 publications

Comparison of molecular structure of alkali metal ortho substituted benzoates

Comparison of molecular structure of alkali metal ortho substituted benzoates

Spectroscopic (FT-IR, FT-Raman,1H and13C NMR) and theoretical studies ofp-coumaric acid and alkali metalp-coumarates

Molecular Structure and Antioxidant Properties of Alkali Metal Salts of Rosmarinic Acid. Experimental and DFT Studies

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Spectroscopic (FT-IR, FT-Raman,¹H and¹³C NMR) and theoretical studies ofp-coumaric acid and alkali metalp-coumarates