5,5′-Dinitro-2,2′-dithiodipyridine

Brito, Iván; Mundaca, Aldo; Cárdenas, Alejandro; López-Rodríguez, Matías; Vargas, Diego A.

doi:10.1107/s1600536807031091

Cited by 7 publications

(4 citation statements)

References 21 publications

(36 reference statements)

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“…1) is presented by the 5 nitro pyridinethiol 2 ate anion and the hydrazinium cation NH 2 N All bond lengths and bond angles in struc ture III are consistent with those observed in the organic structures containing similar ions [29,30]. The nitro group in the anion deviates from the plane of the pyridine cycle by 5.9°.…”

Section: Resultssupporting

confidence: 75%

Synthesis, structure, and NO-donor activity of bis(5-nitropyridine-2-thiolato)tetranitrosyliron

et al. 2012

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A new method is developed for the synthesis of the binuclear iron tetranitrosyl complex with 5 nitropyridine 2 thiolate, [Fe 2 (SC 5 H 3 N 2 O 2 ) 2 (NO) 4 ] (I), from 2,2' dithiobis(5 nitropyridine) and hydra zine hydrate in an aqueous alcohol solution followed by the replacement of the thiosulfate ligands in an aque ous solution of salt Na 2 [Fe 2 (S 2 O 3 ) 2 (NO) 4 ] ⋅ 4H 2 O by functional 5 nitropyridine 2 thiolates. It is established by the X ray diffraction method that the complex has the structure of the μ SR type and crystallizes as two polymorphs. The Moessbauer spectral parameters at 293 K (quadrupole splitting ΔE Q = 1.243(1) mm/s, iso meric shift δ Fe = 0.095(1) mm/s, and absorption line width Γ = 0.263(1) mm/s) for studied compound I are similar to the isoelectronic complexes with thiophenoxide, pyridyl 2 thiolate, and pyrimidyl 2 thiolate. According to the electrochemical analysis data, complex I is a more efficient donor of NO in hydrolytic decomposition in protic media with NO formation than its isostructural analog with the unsubstituted pyridylthiolate ligand. The maximum amount of NO generated by complex I in a 1% aqueous solution of dimethyl sulfoxide at T = 25°C and pH 7.0 is 7.4 nmoles and increases twofold with an increase in the acidity of the medium (to pH 6.5) or temperature (37°C).

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Section: Resultssupporting

confidence: 75%

Synthesis, structure, and NO-donor activity of bis(5-nitropyridine-2-thiolato)tetranitrosyliron

et al. 2012

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“…The synthesis of the title compound has been previously reported (Allinger & Youngdale, 1962), although by different methods from the preparation of the sample used for this study [a modification of the method given by Lu et al (2006)]. For related structures, see: Barnes et al (1981); Brito et al (2007); Cousson et al (1993); Housty (1961).…”

Section: Related Literaturementioning

confidence: 99%

Bis(2-nitrophenyl)methane

Janzen¹,

Crepeau²,

Hageseth³

et al. 2014

Acta Cryst E

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In the title compound, C13H10N2O4, the nitro groups are twisted significantly relative to the benzene rings [dihedral angles = 16.64 (18) and 28.02 (11)°]. The benzene groups are nearly perpendicular to each other [dihedral angle = 87.72 (6)°]. Short intermolecular N⋯O and C⋯O [2.981 (2) and 3.060 (2) Å, respectively] contacts suggest possible weak π-interactions between nitro groups and between benzene and nitro groups. In addition, there are π–π interactions between one benzene group and an inversion-related equivalent [interplanar separation = 3.494 (2) Å].

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“…In the title compound, C 10 H 6 N 4 O 4 S 2 , (I), the molecule has a centre of inversion. The structure is a positional isomer of 5,5 0dinitro-2,2 0 -dithiodipyridine [Brito, Mundaca, Cá rdenas, Ló pez-Rodríguez & Vargas (2007). Acta Cryst.…”

mentioning

confidence: 92%

3,3′-Dinitro-2,2′-dithiodipyridine

et al. 2008

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In the title compound, C(10)H(6)N(4)O(4)S(2), (I), the molecule has a centre of inversion. The structure is a positional isomer of 5,5'-dinitro-2,2'-dithiodipyridine [Brito, Mundaca, Cárdenas, López-Rodríguez & Vargas (2007). Acta Cryst. E63, o3351-o3352], (II). The 3-nitropyridine fragment of (I) shows excellent agreement with the bonding geometries of (II). The most obvious differences between them are in the S-S bond length [2.1167 (12) A in (I) and 2.0719 (11) A in (II)], and in the C-C(ipso)-N(ring) [119.8 (2) degrees in (I) and 123.9 (3) degrees in (II)] and S-C-C [122.62 (18) degrees in (I) and 116.0 (2) degrees in (II)] angles. The crystal structure of (I) has an intramolecular C-H...O interaction, with an H...O distance of 2.40 (3) A, whereas this kind of interaction is not evident in (II). The molecules of (I) are linked into centrosymmetric R(4)(4)(30) motifs by a C-H...O interaction. There are no aromatic pi-pi stacking and no C-H...pi(arene) interactions. Compound (I) can be used as a nucleophilic tecton in self-assembly reactions with metal centres of varying lability.

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5,5′-Dinitro-2,2′-dithiodipyridine

Cited by 7 publications

References 21 publications

Synthesis, structure, and NO-donor activity of bis(5-nitropyridine-2-thiolato)tetranitrosyliron

Synthesis, structure, and NO-donor activity of bis(5-nitropyridine-2-thiolato)tetranitrosyliron

Bis(2-nitrophenyl)methane

3,3′-Dinitro-2,2′-dithiodipyridine

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