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Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides.

ABSTRACT: N-oxides of N-heteroaromatic compounds find widespread applications in various fields of chemistry. Although the strictly planar aromatic structure of 1,10-phenanthroline (phen) is expected to induce unique features of the corresponding N-oxides, so far the potential of these compounds has not been explored. In fact, appropriate procedure has not been reported for synthesizing these derivatives of phen. Now, we provide a straightforward method for the synthesis of a series of mono-N-oxides of 1,10-phenanthrolines. The parent compounds were oxidized by a green oxidant, peroxomonosulfate ion in acidic aqueous solution. The products were obtained in high quality and at good to excellent yields. A systematic study reveals a clear-cut correlation between the basicity of the compounds and the electronic effects of the substituents on the aromatic ring. The UV spectra of these compounds were predicted by DFT calculations at the TD-DFT/TPSSh/def2-TZVP level of theory.

SUBMITTER: Najoczki F

PROVIDER: S-EPMC8231831 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Bis[1-hydroxy-ethyl-idenediphosphon-ato(1-)](1,10-phenanthroline)nickel(II) mono-hydrate.

Project description:In the mononuclear title compound, [Ni(C(2)H(6)O(7)P(2))(2)(C(12)H(8)N(2))]·H(2)O, the Ni(II) atom (site symmetry 2) is bonded to two phosphate-based O,O'-bidentate chelate ligands and one N,N'-bidentate 1,10-phenanthroline ligand, resulting in a slightly distorted cis-NiN(2)O(4) octa-hedral geometry. In the crystal structure, pairs of complexes are linked by double hydrogen bonds, forming a one-dimensional chain-like structure. Aromatic π-π stacking inter-actions [centroid-centroid separation = 3.768 (2) Å] and further hydrogen bonds generate a two-dimensional structure. The water O atom also lies on a crystallographic twofold axis.

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Bis(benzoato-?O,O')(1,10-phenanthroline-?N,N')lead(II) benzoic acid mono-solvate.

Project description:The reaction of lead acetate, benzoic acid and 1,10-phenanthroline (phen) in aqueous solution yielded the title complex, [Pb(C(7)H(5)O(2))(2)(C(12)H(8)N(2))]·C(7)H(6)O(2). In the crystal, the Pb(II) ion is hexa-coordinated by two N atoms from one 1,10-phenanthroline ligand and four O atoms from two chelate benzoate anions. If the second benzoate ligand is treated as one coordination site, the overall coordination may be represented as a distorted pseudo-square pyramid. An inter-molecular O-H?O hydrogen bond links the solvent benzoic acid mol-ecule with a metal-coordinated benzoate ligand. The shortest Pb?Pb distance is 3.864?(4)?Å, indicating a weak metal-metal inter-action. Two complex mol-ecules related by an inversion centre form dimeric units via Pb?O inter-actions of 3.206?(4)?Å.

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Synthesis, Characterization and Photobiological Studies of Ru(II) Dyads Derived from α-Oligothiophene Derivatives of 1,10-Phenanthroline.

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Difluoridodioxido(1,10-phenanthroline)molybdenum(VI).

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Palladium(II) complexes of 1,10-phenanthroline: Synthesis and X-ray crystal structure determination.

Project description:Two palladium(II) complexes, [Pd(phen)(N identical withCCH(3))(2)][O(3)SCF(3)](2) (1) and [Pd(phen)(mu-OH)](2)[O(3)SCF(3)](2).2H(2)O (2) (where phen= 1,10-phenanthroline), have been crystallized following the reaction of Pd(phen)Cl(2) with silver triflate, Ag(O(3)SCF(3)), in acetonitrile and water, respectively. The structures of both complexes are based on a Pd(phen)(2+) metal core, with two acetonitrile molecules binding in a monodentate fashion in complex 1 and two hydroxo bridges holding together two cores to form a dimer in complex 2. Additionally, both complexes present a hydrogen bonded 3-D network involving the triflate anions in 1, and water and triflate anions in 2. Both complexes have been characterized by infrared and (1)H NMR spectroscopy and their crystal structures determined by X-ray crystallography.

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1,10-Phenanthroline-5,6-dione ethanol monosolvate.

Project description:In the title compound, C12H6N2O2·C2H5OH, the mol-ecule of the 1,10-phenanthroline-5,6-dione is approximately planar, with a maximum deviation of 0.051?(1)?Å. In the crystal, mol-ecules are linked by O-H?N and weak C-H?O hydrogen bonds, forming supra-molecular chains propagating along [110]. ?-? stacking inter-actions are observed between the pyridine rings of neighbouring chains, the centroid-centroid separations being 3.6226?(11) and 3.7543?(11)?Å.

| S-EPMC4011276 | biostudies-literature

4,7-Diphenyl-1,10-phenanthroline methanol hemisolvate.

Project description:The asymmetric unit of the title compound, C24H16N2·0.5CH3OH, is comprised of two independent bathophenanthroline mol-ecules (systematic name: 4,7-diphenyl-1,10-phenanthroline) and one methanol mol-ecule. The bathophenanthroline mol-ecules are not planar as there is a considerable rotation of all terminal phenyl rings with respect to the central phenanthroline units [dihedral angles in the range 52.21?(12)-62.14?(10)°]. In addition, a non-negligible torsion is apparent in one of the phenanthroline units: the angle between the mean planes of the two pyridine rings is 14.84?(13)°. The methanol solvent mol-ecule is linked to both N atoms of a bathophenanthroline mol-ecule through a bifurcated O-H?(N,N) hydrogen bond.

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5H-Imidazo[4,5-f][1,10]phenanthroline.

Project description:The title mol-ecule, C(13)H(8)N(4), is is essentially planar [r.m.s. deviation for all non-H atoms = 0.025?(3)?Å]. In the crystal, mol-ecules are connected through one weak bifurcated N-H?(N,N) hydrogen bond and three ?-? stacking inter-actions between pyridine and imidazole rings [centroid-centroid distance = 3.631?(8)?Å] and between pyridine and benzene rings [centroid-centroid distances = 3.675?(5) and 3.666?(2)?Å].

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