Metal–organic coordination architectures of condensed heterocyclic based 1,2,4-triazole: Syntheses, structures and emission properties

Wang, Duo-Zhi; Zhang, Qin; Wu, Yuan-Gao; Cao, Liping; Ma, Peng-Yuan

doi:10.1016/j.poly.2012.05.028

Cited by 9 publications

(2 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The benzyl substituents at C2 for 4c, 4d and 4e destroy the molecular planarity although for 4c and 4d the C1 69 Eleven additional structures are found in which triazolothiadiazole derivatives act as ligands to transition metal complexes, binding to the metal exclusively via the N2 atoms of the triazole rings. 70,71 A significant elongation of the S1C2 distance in comparison to S1C3 bond in the molecules reported here appears from comparison with related compounds to be a characteristic feature of triazolo [3,4-b][1,3,4]thiadiazoles. Only three instances of compounds with furan substituents have been reported previously, two with the furan on the triazole 50−52 and the other on the thiadiazole ring.…”

Section: Resultsmentioning

confidence: 99%

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

Khan

Panini

Khan

et al. 2016

Crystal Growth & Design

View full text Add to dashboard Cite

A detailed analysis of the molecular and crystal packing of a series of pharmaceutically active triazolothiadiazole derivatives is reported. The most notable feature from the analysis of the supramolecular motifs is the presence of inversion dimers due to the formation of strong S•••N chalcogen bonds. This has been unequivocally established via inputs from energy calculations from PIXEL, the topological analysis using the approach of QTAIM from AIMALL, an analysis of the molecular electrostatic potentials plotted on Hirshfeld surfaces, and the analysis of the 3D-deformation densities obtained using Crystal Explorer. The total interaction energy for this contact is in the range of 28−33 kJ/mol in the molecules under investigation, and the electrostatic (Coulombic + polarization) contribution toward the total stabilization energy is more than 70%, indicating that such interactions are principally electrostatic in origin. The results from the analysis of the molecular ESP depict that this interaction exists between a strongly electropositive σ-hole on the sulfur atom and an electronegative region on the nitrogen. 3D-deformation density (DD) maps reveal the presence of a charge depletion (CD) region on the sulfur atom which is directed toward the charge concentration (CC) region on the nitrogen atom facilitating formation of such contacts in the crystal. These are further invesigated by QTAIM based calculations which establish the closed-shell nature of these contacts. The crystal packing is further stabilized by the presence of significantly important π•••π stacking interactions, wherein the interaction energies, calculated by the PIXEL method, reveal that some of these interactions in crystals have significant contributions from electrostatic components, with a lesser contribution from dispersion forces that normally dominate such interactions. The existence of a contribution of ∼48% from electrostatics between stacked rings owing to their unique electrostatic complementarity is a rare supramolecular feature observed in crystal packing in these solids. In addition, the existence of C−H•••O, C−H•••N, C−H•••F, and Cl•••N interactions is also characterized by a significant electrostatic component in their formation in crystals of these compounds.

show abstract

Section: Resultsmentioning

confidence: 99%

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

Khan

Panini

Khan

et al. 2016

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…Heterocyclic ligands have attracted much interest as versatile ligands with a variety of coordination modes with transition metal centres (Galani et al, 2014;Vimal Kumar & Radhakrishnan, 2011;Coropceanu et al, 2014;Wang, Chen et al, 2012). In particular, 1,2,4-triazole derivatives and their metal complexes have been studied extensively in recent years (Naik et al, 2011;Wang, Zhang et al, 2012;Wang et al, 2014;Liu, He et al, 2009), mainly because of their unique structures and their potential applications in optical (Manjunatha et al, 2013), electrical (Luo et al, 2013;Matesanz et al, 2004), and biological and antimicrobial areas (Tabatabaee et al, 2013;Xiong et al, 2014;Singh et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

A new Co^IIcomplex of diniconazole: synthesis, crystal structure and antifungal activity

Yan

et al. 2015

Acta Crystallogr C

View full text Add to dashboard Cite

A new Co(II) complex of diniconazole, namely diaqua[(E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl-κN(4))pent-1-en-3-ol]cobalt(II) dinitrate dihydrate, [Co(C15H17Cl2N3O)3(H2O)2](NO3)2·2H2O, was synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. Crystal structural analysis shows that the centrosymmetric Co(II) cation is coordinated by four diniconazole ligands and two water molecules, forming a six-coordinated octahedral structure. There are also two free nitrate counter-anions and two additional solvent water molecules in the structure. Intermolecular O-H...O hydrogen bonds link the complex cations into a one-dimensional chain. In addition, the antifungal activity of the complex against Botryosphaeria ribis, Gibberella nicotiancola, Botryosphaeria berengriana and Alternariasolani was studied. The results indicate that the complex shows a higher antifungal activity for Botryosphaeria ribis and Botryosphaeria berengriana than diniconazole, but a lower antifungal activity for Gibberella nicotiancola and Alternariasolani.

show abstract

Four cadmium(II) coordination polymers with an N- and O-donor ligand: Structural characterization, in situ reaction and fluorescent property

2013

View full text Add to dashboard Cite

Metal–organic coordination architectures of condensed heterocyclic based 1,2,4-triazole: Syntheses, structures and emission properties

Cited by 9 publications

References 50 publications

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

A new Co^IIcomplex of diniconazole: synthesis, crystal structure and antifungal activity

Four cadmium(II) coordination polymers with an N- and O-donor ligand: Structural characterization, in situ reaction and fluorescent property

Contact Info

Product

Resources

About

Metal–organic coordination architectures of condensed heterocyclic based 1,2,4-triazole: Syntheses, structures and emission properties

Cited by 9 publications

References 50 publications

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S···N and Cl···N Supramolecular Motifs in Crystalline Triazolothiadiazoles

A new CoIIcomplex of diniconazole: synthesis, crystal structure and antifungal activity

Four cadmium(II) coordination polymers with an N- and O-donor ligand: Structural characterization, in situ reaction and fluorescent property

Contact Info

Product

Resources

About

A new Co^IIcomplex of diniconazole: synthesis, crystal structure and antifungal activity