Synthesis, crystal structures and antimicrobial activity of dimeric copper(II) complexes with 2-hydroxyphenyl-ethylidene-dithiocarbazates

Lima, Francielle C.; Silva, Thayná de Souza; Martins, Carlos Henrique Gomes; Gatto, Claudia C.

doi:10.1016/j.ica.2018.08.032

Cited by 29 publications

(14 citation statements)

References 35 publications

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“…The three remaining structures have a methyl substituent at the imine-C atom. Two of these have 2-OH substituents in the benzene ring, one with R = benzyl (QUCLIL; Biswal et al, 2015), with a twisted conformation, and the other with R = CH 2 CH 2 (NILRII; Lima et al, 2018), being a planar molecule. The sixth and final analogue is a 3-OH derivative with R = benzyl (LUBNIH; Zangrando et al, 2015); this molecule exhibits a twisted conformation in its crystal.…”

Section: Database Surveymentioning

confidence: 99%

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

et al. 2020

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The title hydrazine carbodithioate chloroform hemisolvate, 2C15H14N2O2S2·CHCl3, comprises two independent hydrazine carbodithioate molecules, A and B, and a chloroform molecule; the latter is statistically disordered about its molecular threefold axis. The common features of the organic molecules include an almost planar, central CN2S2 chromophore [r.m.s. deviation = 0.0203 Å (A) and 0.0080 Å (B)], an E configuration about the imine bond and an intramolecular hydroxyl-O—H...N(imine) hydrogen bond. The major conformational difference between the molecules is seen in the relative dispositions of the phenyl rings as indicated by the values of the dihedral angles between the central plane and phenyl ring of 71.21 (6)° (A) and 54.73 (7)° (B). Finally, a difference is seen in the disposition of the outer hydroxyl-H atoms, having opposite relative orientations. In the calculated gas-phase structure, the entire molecule is planar with the exception of the perpendicular phenyl ring. In the molecular packing, the A and B molecules assemble into a two-molecule aggregate via N—H...S hydrogen bonds and eight-membered {...HNCS}2 synthons. The dimeric assemblies are connected into supramolecular chains via hydroxyl-O—H...O(hydroxyl) hydrogen bonds and these are linked into a double-chain through hydroxy-O—H...π(phenyl) interactions. The double-chains are connected into a three-dimensional architecture through phenyl-C—H...O(hydroxyl) and phenyl-C—H...π(phenyl) interactions. The overall assembly defines columns along the a-axis direction in which reside the chloroform molecules, which are stabilized by chloroform–methine-C—H...S(thione) and phenyl-C—H...Cl contacts. The analysis of the calculated Hirshfeld surfaces, non-covalent interaction plots and interaction energies confirm the importance of the above-mentioned interactions, but also of cooperative, non-standard interactions such as π(benzene)...π(hydrogen-bond-mediated-ring) contacts.

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Section: Database Surveymentioning

confidence: 99%

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

et al. 2020

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“…1D and 2D NMR spectra were recorded on a Bruker Advance III HD 600 spectrometer (14.1 Tesla) using an inverse detection 5-mm ( 1 H, 13 C, 15 N) cryoprobe and a z gradient, as well as automated tuning and marching (ATM) in (CD 3 ) 2 SO-d6 (99.95%, Sigma-Aldrich) as solvent purchased from Sigma-Aldrich TM, chemical shifts were referenced to tetramethylsilane (TMS). 2.4.…”

Section: Nuclear Magnetic Resonance (Nmr)mentioning

confidence: 99%

“…Biological tests. The MIC values (the lowest concentration of the compound capable of inhibiting microorganism growth) of the Resinic acid, Calcium resinate, Magnesium resinate and Zinc resinate were determined in triplicate by using the microdilution broth method in 96-well microplates, according to Lima et al, [13] with some modification.…”

Section: Nuclear Magnetic Resonance (Nmr)mentioning

confidence: 99%

“…The microplates (96 -wells) were sealed with plastic film and the time needed to promote growth was 24 hours, incubated at 37 o C under appropriate gaseous conditions. After that, resazurin (Sigma-Aldrich) -30 L in aqueous solution (0.02%) was added to the microplates, to indicate microorganism viability, the blue and red color indicated absence and presence of bacterial growth, respectively, for the determination of minimal inhibitory concentration [13].…”

Section: Assessment the Antibacterial Activity For Determination Of Mmentioning

confidence: 99%

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Obtaining salts of resin acids from Cuban pine by metathesis reactions

2020

Biointerface Res Appl Chem

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The resin acids obtained from the Cuban pine rosin are the starting material for the development and application of metathesis reactions. These reactions allow the obtaining of salts with high added value which could be used in the development of biomaterials for dental use. The objective of this work was to obtain calcium, magnesium and zinc resinates from the resin acid obtained from the Cuban pine resin by metathesis reaction for possible use in the development of biomaterials. The products obtained were evaluated by elemental analysis, X-ray powder diffraction, infrared spectroscopy, scanning electron microscopy associated with electron dispersion spectroscopy, nuclear magnetic resonance and biological tests (antibacterial activity). The results showed the formation of the different resinates, observing the presence of cations in the salts obtained. The disappearance of the signal corresponding to the hydrogen of the carboxyl group was verified by nuclear magnetic resonance analysis due to the reaction between the resinic acid and the different metals studied. The biological analyzes showed that the best results are achieved with zinc resinate.

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“…Schiff bases display significant biological and pharmacological activities that can be tuned by incorporating different types of substituents through the condensation reaction (How et al, 2008;Low et al, 2016). Transition-metal complexes containing Schiff base ligands have also been intensively studied because of their simple routes of synthesis, the variety of their structural geometries and, particularly pertinent, as small chemical changes often produce wide variations in their bioactivities (Mirza et al, 2014;Zangrando et al, 2015;Lima et al, 2018). Recently, a copper(II) dithiocarbazate complex containing a Schiff base derived from S-hexyldithiocarbazate and 4-methylbenzaldehyde was reported to have excellent anti-bacterial activity against Escherichia coli (Zangrando et al, 2017).…”

Section: Chemical Contextmentioning

confidence: 99%

Bis[S-benzyl 3-(furan-2-ylmethylidene)dithiocarbazato-κ² N ³,S]copper(II): crystal structure and Hirshfeld surface analysis

et al. 2019

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The title CuII complex, [Cu(C13H11N2OS2)2], features a trans-N2S2 donor set as a result of the CuII atom being located on a crystallographic centre of inversion and being coordinated by thiolate-S and imine-N atoms derived from two dithiocarbazate anions. The resulting geometry is distorted square-planar. In the crystal, π(chelate ring)–π(furyl) [inter-centroid separation = 3.6950 (14) Å and angle of inclination = 5.33 (13)°] and phenyl-C—H...π(phenyl) interactions sustain supramolecular layers lying parallel to (\overline{1}02). The most prominent interactions between layers, as confirmed by an analysis of the calculated Hirshfeld surface, are phenyl-H...H(phenyl) contacts. Indications for Cu...Cg(furyl) contacts (Cu...Cg = 3.74 Å) were also found. Interaction energy calculations suggest the contacts between molecules are largely dispersive in nature.

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Synthesis, crystal structures and antimicrobial activity of dimeric copper(II) complexes with 2-hydroxyphenyl-ethylidene-dithiocarbazates

Cited by 29 publications

References 35 publications

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

Obtaining salts of resin acids from Cuban pine by metathesis reactions

Bis[S-benzyl 3-(furan-2-ylmethylidene)dithiocarbazato-κ² N ³,S]copper(II): crystal structure and Hirshfeld surface analysis

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Synthesis, crystal structures and antimicrobial activity of dimeric copper(II) complexes with 2-hydroxyphenyl-ethylidene-dithiocarbazates

Cited by 29 publications

References 35 publications

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

Obtaining salts of resin acids from Cuban pine by metathesis reactions

Bis[S-benzyl 3-(furan-2-ylmethylidene)dithiocarbazato-κ2 N 3,S]copper(II): crystal structure and Hirshfeld surface analysis

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Bis[S-benzyl 3-(furan-2-ylmethylidene)dithiocarbazato-κ² N ³,S]copper(II): crystal structure and Hirshfeld surface analysis