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Tweaking the affinity of aryl-substituted diazosalicylato- and pyridine ligands towards Zn (II) and its neighbors in the periodic system of the elements, Cu (II) and Cd (II), and their antimicrobial activity

A series of six new Zn (II) compounds, viz., [Zn(HLASA)2(Py)2] (1), [Zn(HLMASA)2(Py)2] (2), [Zn(HLMASA)2(4-MePy)2] (3), [Zn(HLCASA)2(4-MePy)2] (4), [Zn(HLBASA)2(Py)2] (5), [Zn(HLBASA)2(4-MePy)2] (6) and representative Cu (II) and Cd (II) complexes, viz., [Cu(HLASA)2(Py)2(H2O)] (7) and [Cd(HLBASA)2(Py)3] (8) [(HLXASA)??=?para-substituted 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoate with X?=?H (ASA), Me (MASA), Cl (CASA) or Br (BASA); Py?=?pyridine; 4-MePy?=?4-methylpyridine] have been synthesized and characterized by spectroscopic techniques and single-crystal X-ray diffraction analysis. The structural characterization of the compounds revealed distorted tetrahedral (1–6), square-pyramidal (7) and pentagonal-bipyramidal (8) coordination geometries around the metal atom, in which the aryl-substituted diazosalicylate ligands are coordinated only through the oxygen atoms of carboxylate groups, either in an anisobidentate or isobidentate mode; meanwhile, the 2-hydroxy groups of the monoanionic ligand (HLXASA)? are involved only in intramolecular O-H···O hydrogen bonds with the carboxylate function. In the crystal structures of 1–8, the complex molecules are assembled by π-stacking interactions giving mostly infinite 1D strands. The intermolecular binding in the solid state structures is accomplished by diverse additional non-covalent contacts including C-H···O, C-H···N, C-H···π, C-H···Br, O···Br, Br···π and van der Waals contacts. Although the primary and secondary ligands in the Zn (II) complex series 1–6 carry different substituents at the periphery (X?=?H, Me, Cl, Br for (HLXASA)? and R?=?H, Me for 4-Py-R), five of the crystal structures were isostructural. Additionally, the antimicrobial activity of the pro-ligands H2LXASA and their Zn (II), Cu (II) and Cd (II) compounds were studied in a comparative manner, showing high sensitivity (IZD?≥?20) against Bacillus subtilis.

Mono- and di-anionic coordination modes of arylazosalicylates in their bis(η5-cyclopentadienyl)titanium(IV) complexes: Syntheses and crystal structures

The bis(η5-cyclopentadienyl)titanium(IV) complexes of 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids (H2LXASA) where the aryl group is an X-substituted phenyl ring such that X = CH, COEt, CMe, CF, CCl, CBr and N have been synthesised. Two types of titanium(IV) compounds viz. (i) [Ti(η5-C5H5)2(O2CC6H3(OH-2)(N[dbnd]NC6H4(H-4)-5))2] (3) and [Ti(η5-C5H5)2(O2CC6H3(OH-2)(N[dbnd]NC6H4(OC2H5-4)-5))2] (4), and (ii) [Ti(η5-C5H5)2(O2CC6H3(O-2)(N[dbnd]NC6H4(CH3-4)-5))] (5), [Ti(η5-C5H5)2(O2CC6H3(O-2)(N[dbnd]NC6H4(F-4)-5))] (6), [Ti(η5-C5H5)2(O2CC6H3(O-2)(N[dbnd]NC6H4(Cl-4)-5))] (7), [Ti(η5-C5H5)2(O2CC6H3(O-2)(N[dbnd]NC6H4(Br-4)-5))] (8) and [Ti(η5-C5H5)2(O2CC6H3(O-2)(N[dbnd]NC5H4(N-4)-5))] (9) were isolated and characterised by IR, 1H and 13C NMR spectroscopic techniques. The crystal and molecular structures of 3–9 have been determined by single crystal X-ray crystallography. Compounds 3 and 4 conform to the formula Cp2Ti(HLXASA-κO)2 with a monodentate carboxylate ligand while those of 5–9 conform to Cp2Ti(LXASA-κ2O1,O2) with the dianions chelating the titanium atoms via carboxylate-O and hydroxy-O atoms. The common feature of the molecular structures is the adoption of distorted tetrahedral geometries based (Cp)2O2 donor sets. Hydroxyl–O–H…O(carbonyl) bonding leads to supramolecular chains in the crystal of 4 but, these are absent in 3. Persistent Cp–C–H…O(carbonyl) interactions, with the carbonyl atoms accepting two or three such interactions, lead to supramolecular chains with helical (5, 7 and 8) or linear (6 and 9) topologies; C–X…π interactions also play an important role in the packing of 6–8.

Synthesis and characterization of triorganotin(IV) complexes of 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids. Crystal and molecular structures of a series of triphenyltin 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoates (aryl = phenyl, 2-methylphenyl, 3-methylphenyl and 4-methoxy...)

The triphenyltin and tri-n-butyltin complexes of some 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids have been synthesized and characterized by 1H-, 13C-, 119Sn-NMR, IR and 119mSn Moessbauer spectroscopic techniques in combination with elemental analysis. The crystal structures of triphenyltin 5-[(E)-2-(aryl-1-diazenyl]-2-hydroxybenzoates (aryl = phenyl, 2-methoxyphenyl, 3-metylphenyl and 4-methoxyphenyl) are reported. Both X-ray and 119Sn Moessbauer data indicate that the triphenyltin complexes adopt a monomeric distorted tetrahedral configuration with the carboxylate ligand coordinating in a monodentate mode. By contrast, 119Sn Moessbauer spectroscopy shows that each tributyltin complex is polymeric and features a trans-trigonal bipyramidal geometry with a planar SnBu3 unit and two apical carboxylate oxygen atoms derived from bidentate bridging carboxylate ligands. This is a solid-state effect, as both 119Sn-NMR and 1(13C-119/117Sn) coupling constant data indicate tetrahedral geometries in solution for the triphenyl and tri-n-butyl complexes.