The Crystal Structure of Copper(II) 2-(o-Hydroxyphenyl)benzoxazole.

Sténson, Per; Jacobsen, G. G.; Seip, H. M.; Holme, Tord; Lindberg, Alf A.; Jansen, Gert; Lamm, Bo; Samuelsson, Benny

doi:10.3891/acta.chem.scand.23-1514

Cited by 21 publications

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“…33,34) In the Cu(II) complex 2f, the Cu(II) atom was coordinated by two N atoms and two O atoms from two 1a, forming a strictly square planar geometry (dihedral angle between two N-Cu-O planes: 0°). [35][36][37] In the Pd(II) complex 2g, the geometry at Pd(II) center was coordinated as nearly perfect square planar which are similar to that of the Cu(II) atom in 2f. 38) The crystal structure of Ag(I) complex 2h revealed to consist a 1 : 1 metal-ligand molar ratio and the Ag(I) ion exhibits a distorted trigonal pyramidal geometry by two 1a and the another Ag(I) atom, forming a 4-membered parallelogram Ag 2 O 2 ring.…”

Section: )mentioning

confidence: 92%

“…1 [29][30][31][32][33][34][35][36][37][38][39] In the Zn(II) complex 2b, the geometry at the Zn(II) center can be best described as a distorted tetrahedron in which two benzoxazole-2-chlorodifluoroacetonate (1b) ligands are placed in a similar disposition about the zinc center. [29][30][31] One coordination plane (N-O-Zn) in 2b is approximately perpendicular to the other with a dihedral angle of 89.2°.…”

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confidence: 99%

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Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

et al. 2018

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Key words antibacterial activity; fluorinated benzoxazole; metal complex; trifluoroacetylBacterial infection remains a serious threat to human lives due to rapid development of resistance to the existing antibiotics. In order to prevent this major medical problem, the discovery of new types of antimicrobial agents is a very important but challenging task.1,2) Transition metal complexes have received great attention because many drugs such as antibiotics and quinolone antibiotics possess better pharmaceutical properties when they are in the form of metal complexes. 3-7)Benzoxazole heterocycle system is an important pharmacophore and privileged structure in the medicinal chemistry. 8-10)Its derivatives and particularly, 2-substituted benzoxazoles exert various biological activities such as antimicrobial, antiviral, antifungal, and anticancer. [11][12][13][14][15] In previous studies, we have identified 2-trifluoroacetonylbenzoxazole (1a) with in vitro antimicrobial activity against Helicobacter pylori and Escherichia coli (Ec) from our compound library of trifluoromethyl ketones obtained by our developed reactions. 16,17) The heteroaryl-substituted alkenol systems such as 1a are known to chelate some metal ions such as aluminum 18) and to form a stable six-membered metal complexes in a bidentate mode, where the complexes were reinforced by a positive inductive effect of the heterocyclic moiety and a negative inductive effect of the CF 3 groups. [19][20][21][22][23] In the light of these knowledge, three 2-fluoroacetonylbenzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been synthesized in order to check how the metal ion binding may influence their antibacterial activity (Chart 1). In addition, syntheses of new metal [Mg(II), Ni(II), Cu(II), Pd(II), and Ag(I)] complexes 2d-h from 1a have been also described ( Table 1). The structures of six metal complexes 2b and 2d-h were determined by single-crystal X-ray diffraction analyses. In vitro antimicrobial activities of the ligands 1a-c and their metal complexes 2a-h were investigated against six Gram-positive (G(+)) and six Gram-negative (G(−)) bacteria and the results were compared with those of silver nitrate and appropriate antibiotics such as Kanamycin, Gentamicin, Norfloxacin, and/or Linezolid. The most potent Ag(I) complex 2h is bacteriostatic, disrupts membrane integrity observed by scanning electron microscopy (SEM) and is less likely to develop resistance development against Pseudomonas aeruginosa (Pa). Results and DiscussionChemistry First, three benzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been prepared in order to investigate the relationship of the ligands and their Zn(II) complexes with their antibacterial activities.Our synthetic protocol to obtain the ligand 1a consists of a trifluoroacetylation of 2-methylbenzoxazole with trifluoroacetic anhydride (TFAA) in the presence of pyridine 24) (Chart 1). The Zn(II) complex 2a was prepared by the reaction of 1a with zinc dust in MeCN in 78% yield, consisting of 1a with zinc(...

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confidence: 92%

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confidence: 99%

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

et al. 2018

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Komplexchemisches Verhalten von N‐substituierten 2‐(oHydroxyphenyl)‐Δ²‐imidazolinen als Metallextraktionsmittel

et al. 1983

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The Coordinative Behaviour of N‐Substituted 2‐(Δ2‐Imidazolin‐2‐yl)‐phenols as Metal Extractants N‐Substituted 2‐(Δ2‐imidazolin‐2‐yl)‐phenols (R4NNOH) are obtained by the reaction of N‐alkyl diaminoethane‐1, 2 and 2‐hydroxybenzoic acid esters. In contrast to many other copper(II) complexes with the donor set N2O22−(A), the species Cu(R4NNO)2(B) are easily soluble in nonpolar solvents. The reason is the monomeric square‐planar structure of B, which differs from the polymeric distorted octahedral structure of A. The two maxima in the vis‐spectra of Cu(R4NNO)2 and Ni(R4NNO)2 are assigned to the 3 dxy → 3 dx2‐y2 and the 3 dxz, 3 dyz → 3 dx2‐y2 electron transitions. The shift of these maxima, which is connected with the dissolution in chloroform, is explained by the formation of hydrogen bonds between the solvent and the N‐alkylated nitrogen atoms of the ligands. 1H‐n. m. r.‐spectra and solubility of the ligands and the crystal structure of Cu[(C4H9)NNO]2 are described.

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Substituierte 2‐(Thiazol‐4‐yl)‐phenole als Liganden und potentielle Extraktionsmittel für Kupfer(II)

Dinjus¹,

Uhlig²,

Beger³

et al. 1981

Zeitschrift anorg allge chemie

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Durch die HANTZSCHsche Synthese werden substituierte 2‐(Thiazol‐4‐yl)‐phenole HLn hergestellt. Ihre Löslichkeit ist in Toluen besser als in n‐Octan und hängt von der Stellung, der Kettenlänge und der Polarität der Substituenten ab. Aus alkoholischen Lösungen kristallisieren Komplexe des Typs CuL2n. Je nach den Substituenten ist ihre Struktur verzerrt oktaedrisch (CuL22, CuL23) oder verzerrt tetraedrisch (CuL28, CuL29). Alle neu dargestellten Kupfer(II)‐Komplexe sind in Toluen und aliphatischen Kohlenwasserstoffen schwer löslich. Dagegen lösen sich die Verbindungen CuL28 und CuL29 gut in Chloroform. Kupfer(II) kann daher mit HL8 und HL9 in Chloroform als Verdünnungsmittel extrahiert werden.

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The Crystal Structure of Copper(II) 2-(o-Hydroxyphenyl)benzoxazole.

Cited by 21 publications

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Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Komplexchemisches Verhalten von N‐substituierten 2‐(oHydroxyphenyl)‐Δ²‐imidazolinen als Metallextraktionsmittel

Substituierte 2‐(Thiazol‐4‐yl)‐phenole als Liganden und potentielle Extraktionsmittel für Kupfer(II)

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The Crystal Structure of Copper(II) 2-(o-Hydroxyphenyl)benzoxazole.

Cited by 21 publications

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Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Komplexchemisches Verhalten von N‐substituierten 2‐(oHydroxyphenyl)‐Δ2‐imidazolinen als Metallextraktionsmittel

Substituierte 2‐(Thiazol‐4‐yl)‐phenole als Liganden und potentielle Extraktionsmittel für Kupfer(II)

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Komplexchemisches Verhalten von N‐substituierten 2‐(oHydroxyphenyl)‐Δ²‐imidazolinen als Metallextraktionsmittel