Metal coordination compounds derived from tinidazole and transition metals. Halogen and oxygen lone pair···π interactions

Alfaro-Fuentes, Israel; López-Sandoval, Horacio; Mijangos, Edgar; Duarte-Hernández, Angélica M.; Rodríguez‐López, Germán; Bernal-Uruchurtu, Margarita I.; Contreras, Rosalinda; Flores‐Parra, Angelina; Barba-Behrens, Noráh

doi:10.1016/j.poly.2013.09.030

Cited by 17 publications

(9 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The np* interaction plays a significant role in the structures of not only biomacromolecules but also materials. [78][79][80][81][82][83][84][85] There are quite extensive reports in the literature which show the existence of the np* interaction as well as its role in the supramolecular self assembly of molecules to give rise to specific structures of materials. Reedijk and co-workers have named this interaction as a new supramolecular bond.…”

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

The n → π* interaction: a rapidly emerging non-covalent interaction

Singh

Das

2015

Phys. Chem. Chem. Phys.

255

216

View full text Add to dashboard Cite

This perspective describes the current status of a recently discovered non-covalent interaction named as the n → π* interaction, which is very weak and counterintuitive in nature. In this review, we have provided a brief overview of the widespread presence of this interaction in biomacromolecules, small biomolecules and materials, as well as the physical nature of this interaction explored using various experimental and theoretical techniques. It has been found that this interaction is equally important to other non-covalent interactions for the stability and specific structures of biomolecules and materials. An in-depth understanding of this interaction can help in designing more efficient functional materials as well as drugs. The review also provides a future outlook in terms of exploring the detailed functional role of this interaction in biological processes and its direct spectroscopic evidence, which other commonly known non-covalent interactions (conventional hydrogen bonding, π-hydrogen bonding, π-stacking, etc.) have.

show abstract

Section: Significance Of the Np* Interaction In Materialsmentioning

confidence: 99%

The n → π* interaction: a rapidly emerging non-covalent interaction

Singh

Das

2015

Phys. Chem. Chem. Phys.

255

216

View full text Add to dashboard Cite

show abstract

“…The copper-containing reactant Cu(NO 3 ) 2 Á3H 2 O and ethanol solvent were of Merck reagent grade and were employed without further purification. The [Cu(NO 3 ) 2 (tnz) 2 ] complex was obtained following the procedure reported by Alfaro-Fuentes et al (2014) by adding the respective salt dissolved in ethanol and then mixing with a hot ethanol solution of tinidazole. The mixture was refluxed for 4 h, followed by rapid cooling in an ice bath.…”

Section: Methodsmentioning

confidence: 99%

Molecular structures of two copper complexes with the pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction

Zapata¹,

Carmona²,

Echeverría³

et al. 2022

Acta Crystallogr Sect B

View full text Add to dashboard Cite

The crystal structures of bis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-ium-4-yl)-1,4-dihydroquinoline-3-carboxylato]copper(II) sulfate heptahydrate, [Cu(C16H18FN3O3)2]SO4·7H2O or [Cu(nor)2]SO4·7H2O (nor is norfloxacin), and bis{1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimide}dinitratocopper(II), [Cu(NO3)2(C8H13N3O4S)2] or [Cu(NO3)2(tnz)2] (tnz is tinidazole), were solved by X-ray diffraction. Both complexes crystallize in the space group P21/c, with Z = 4 (for nor) and Z = 2 (for ntz) molecules per unit cell. In [Cu(nor)2]SO4·7H2O, the CuII ion is at the centre of a square-planar environment, trans coordinated to two independent norfloxacin molecules in the zwitterionic form acting as bidentate ligands through one of the carboxyl (cbx) and the carbonyl (cb) O atoms. The solid is further stabilized by an extensive network of N—H...O(sulfate), N—H...O(cbx), N—H...OW, OW—H...O(sulfate) and OW—H...OW hydrogen bonds. The [Cu(NO3)2(tnz)2] complex is centrosymmetric, with the CuII ion in a square planar environment, coordinated to a tinidazole molecule acting as a monodentate ligand through its imidazole N atom and to one nitrate O atom. The vibrational FT–IR absorption spectra and thermal behaviour of the complexes were also studied and are briefly discussed based on the crystal structures.

show abstract

“…Particularly, the asymmetric NO 2 stretching vibration 19,20,40 (observed at 1522 cm −1 in pure TNZ) from the TNZ component of TNZ-CAshifted hypsochromically, like in TNZ-PABA and TNZ-SA cocrystals, and its wavenumber (1540 cm −1 ) was similar to those of TNZ-PABA (1539 cm −1 ) and TNZ-SA (1537 cm −1 ). Taking into account that, in the crystal packing of the reported crystal structure of TNZ (CSD, 22 Refcode CEPSIZ) 41 21 the shift to a higher frequency of the asymmetric NO 2 stretching band of TNZ-CA is consistent with weak H-bonding and with the disruption of the TNZ tetramer, as observed in the crystal structures of TNZ-PABA (Figure 5a) and TNZ-SA (Figure 7a) cocrystals, thus confirming that the crystal structure of TNZ was changed in TNZ-CA.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The biological relevance, limited solubility, photochemical instability in the solid state, − and interesting structural properties of TNZ (due to the presence of a flexible chain and coordinating sites, as lone pairs and delocalized π-electrons), together with the lack of definitive previously published results, motivated us to investigate its capability of forming cocrystals and eutectics with pharmaceutically acceptable coformers and thus diversifying the novel crystal forms, which might then improve its aqueous solubility and physical stability. A careful literature and Cambridge Structural Database (CSD) search (version 5.40, updated to August 2019) showed that no cocrystal structures of TNZ have been reported.…”

Section: Introductionmentioning

confidence: 99%

Novel Cocrystals and Eutectics of the Antiprotozoal Tinidazole: Mechanochemical Synthesis, Cocrystallization, and Characterization

Fandiño

Reviglio

Linck

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

Antiprotozoal tinidazole (TNZ) exhibits low aqueous solubility (Sw) and poor photochemical stability. In this work, TNZ was used to form cocrystals and eutectics with the aim of enhancing its solubility and physical stability. The choice of coformers was based on a crystal engineering strategy focused on the success rate of supramolecular heterosynthon formation between azoles and carboxylic acids. By liquid-assisted grinding, three cocrystals [with p-aminobenzoic acid (PABA), citric acid (CA), and salicylic acid (SA)] and two eutectics [with nicotinamide and succinic acid] were obtained and characterized using powder X-ray diffraction, 13 C solid-state nuclear magnetic resonance, infrared spectroscopy, differential scanning calorimetry, thermogravimetry, and hot-stage microscopy. The crystal structures of TNZ-PABA and TNZ-SA were resolved by means of single-crystal X-ray diffraction, which revealed that they are a solvated and an unsolvated cocrystal, respectively. The Sw values of the obtained samples were determined at 37 °C, with the outcome that only the TNZ-CA cocrystal had a slightly higher Sw than pure TNZ. A physical stability study was also performed under UV−visible irradiation, and it was found that the three cocrystals showed better photostability when compared to TNZ, the two eutectics, and each respective physical mixture, a finding that could be relevant from the pharmacotechnical point of view.

show abstract

Metal coordination compounds derived from tinidazole and transition metals. Halogen and oxygen lone pair···π interactions

Cited by 17 publications

References 25 publications

The n → π* interaction: a rapidly emerging non-covalent interaction

The n → π* interaction: a rapidly emerging non-covalent interaction

Molecular structures of two copper complexes with the pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction

Novel Cocrystals and Eutectics of the Antiprotozoal Tinidazole: Mechanochemical Synthesis, Cocrystallization, and Characterization

Contact Info

Product

Resources

About