Structure and properties of the sodium, potassium and calcium salts of 2-(2,3-dimethylphenyl)aminobenzoic acid

Kruszyński, Rafał; Trzęsowska-Kruszyńska, Agata; Majewski, Piotr; Łukaszewicz, Ewa; Majewska, K.; Sierański, Tomasz; Lewinski, Bartlomiej

doi:10.1016/j.molstruc.2010.02.045

Cited by 6 publications

(7 citation statements)

References 35 publications

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“…The analysed compound exhibits a molecular structure analogous to the coordination of the polymer of sodium diaquamefenamate-water (1/1) reported by Kruszynski et al (2010). The geometry of the chains built up from the sodium ions bridged by water molecules as well as the special arrangement of fenamate and mefenamate ions are distinctly similar.…”

Section: Resultssupporting

confidence: 57%

“…One can expect that the salts of fenamic acids with sodium or potassium will have improved solubility in water, which can result in higher bioaccessibility and reduction of undesired side effects. There are known salts of mefenamic acid with sodium, potassium and calcium and their crystal structures were investigated (Kruszynski et al, 2010), revealing the formation of polymeric structures. The crystals are stable and soluble in water.…”

Section: Introductionmentioning

confidence: 99%

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The Na—O bond in sodium fenamate

Krawczyk

Majerz

2019

Acta Crystallogr Sect B

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The one‐dimensional polymeric structure of sodium diaquafenamate–water (1/1) was studied by X‐ray diffraction. The sodium cation is coordinated to one oxygen atom of the carboxylate group and to four water oxygen atoms. To characterize the Na—O bonds, the quantum theory of atoms in molecules (QTAIM) and noncovalent interaction (NCI) approaches have been used. Both methods confirmed that the Na—O bonds are very weak, comparable with the weak N—H…O intramolecular hydrogen bond. The polymeric structure is stabilized by the interaction of the sodium cation with the surrounding water molecules.

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Section: Resultssupporting

confidence: 57%

Section: Introductionmentioning

confidence: 99%

The Na—O bond in sodium fenamate

Krawczyk

Majerz

2019

Acta Crystallogr Sect B

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“…Our vibrational analysis has considered the differences between the bands in Raman and infrared spectra owing to the existence of centrosymmetric dimers. This kind of analysis was not contemplated in previous studies where DFT calculations were used to investigate the vibrational properties of the MEF I dimer, 21 or the properties of the MEF I and MEF II monomers. 48 The high wavenumber region in the FT-Raman (Figure 6) and FTIR (Figure 7) spectra bands can be used to distinguish the polymorph forms.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…20 Despite the pharmaceutical importance of mefenamic acid polymorphism, a complete spectroscopic characterization of its polymorphs has not yet been performed. Although Kruszynski et al 21 have already compared the experimental and calculated vibrational spectrum of mefenamic acid, only the dimer of polymorph I was considered. In addition, the differences in the infrared and Raman spectra, due to the presence of the centrosymmetric dimer, were not highlighted.…”

Section: ■ Introductionmentioning

confidence: 99%

Mefenamic Acid Anti-Inflammatory Drug: Probing Its Polymorphs by Vibrational (IR and Raman) and Solid-State NMR Spectroscopies

et al. 2014

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This work deals with the spectroscopic (supported by quantum chemistry calculations), structural, and morphological characterization of mefenamic acid (2-[(2,3-(dimethylphenyl)amino] benzoic acid) polymorphs, known as forms I and II. Polymorph I was obtained by recrystallization in ethanol, while form II was reached by heating form I up to 175 °C, to promote the solid phase transition. Experimental and theoretical vibrational band assignments were performed considering the presence of centrosymmetric dimers. Besides band shifts in the 3345-3310 cm(-1) range, important vibrational modes to distinguish the polymorphs are related to out-of-phase and in-phase N-H bending at 1582 (Raman)/1577 (IR) cm(-1) and 1575 (Raman)/1568 (IR) cm(-1) for forms I and II, respectively. In IR spectra, bands assigned to N-H bending out of plane are observed at 626 and 575 cm(-1) for polymorphs I and II, respectively. Solid-state (13)C NMR spectra pointed out distinct chemical shifts for the dimethylphenyl group: 135.8 to 127.6 ppm (carbon bonded to N) and 139.4 to 143.3 ppm (carbon bonded to methyl group) for forms I and II, respectively.

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“…It also displays analgesic, anti-inflammatory, antipyretic, antioxidant and antiproliferative activity. Therefore, it is an important nonsteroidal drug used for treatment moderate pain of various origins (dysmenorrhea, rheumatic diseases, sciatica, headache, premenstrual syndrome, postoperative, posttraumatic and dental pains) [7,8]. Also, mefenamic acid shows therapeutic effects as anticancer agent (particularly colon and liver cancer cell lines) [9,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectral and thermal study of La(III), Nd(III), Sm(III), Eu(III), Gd(III) and Tb(III) complexes with mefenamic acid

Zapała

Kosińska

Woźnicka

et al. 2015

J Therm Anal Calorim

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New binuclear complexes of La(III), Nd(III), Sm(III), Eu(III), Gd(III) and Tb(III) ions with mefenamic acid were obtained in solid phase. For all compounds considered, complexation occurs at pH 6-6.5. The analyzed complexes were characterized on the basis of chemical and elemental analyses, molar conductance, UVVis, IR and 1H NMR spectroscopies as well as thermoanalytical techniques. According to the research results, the molecular formula of the complexes is Ln 2 (C 15 H 14 NO 2 ) 3 (OH) 3 9nH 2 O, with the exception of the La(III) complex which has the formula La 2 (C 15 H 14 NO 2 ) 5 (OH). The results show that only the carboxyl group is involved in the coordination of the rare earth ions in the bidentate mode. Coordination does not occur through the nitrogen atom. All the complexes are soluble in DMSO, and they are nonelectrolytes. The TG-FTIR technique was employed in order to study a decomposition pathway of the obtained compounds. The received results provide information on the composition, thermal stability, thermal decomposition, as well as the gaseous products that evolved during the thermal decomposition of the considered compounds.

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Structure and properties of the sodium, potassium and calcium salts of 2-(2,3-dimethylphenyl)aminobenzoic acid

Cited by 6 publications

References 35 publications

The Na—O bond in sodium fenamate

The Na—O bond in sodium fenamate

Mefenamic Acid Anti-Inflammatory Drug: Probing Its Polymorphs by Vibrational (IR and Raman) and Solid-State NMR Spectroscopies

Synthesis, spectral and thermal study of La(III), Nd(III), Sm(III), Eu(III), Gd(III) and Tb(III) complexes with mefenamic acid

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