A centric organic disulfide (C-S-S-C = 180.degree.): crystal and molecular structures of chloro[bis(2-pyrimidyl) disulfide]copper(I) monohydrate and of bis(2-pyrimidyl) disulfide

Simmons, Charles J.; Lundeen, Munime; Seff, K.

doi:10.1021/ic50202a031

Cited by 34 publications

(6 citation statements)

References 3 publications

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“…The C−Se−Se−C torsion angle and the Se−Se and the Se−C bond lengths of 2.2969(9) (Se1−Se2), 1.932(6) (Se1−C1), and 1.934(6) Å (Se2−C6) are in accordance with the values in other aromatic diselenides, ranging from 2.29(1) to 2.343(1) Å for Se−Se and from 1.910 to 1.934(6) Å for Se−C. (For disulfides a correlation between shorter S−S bonds and 0°/180° X−C−S−S torsion angles has been discussed in terms of interactions of sulfur 3pπ orbitals with the aromatic π system) . The coordination at selenium can be regarded as essentially tetrahedral (C1−Se1−Se2 = 102.8(2)°, Se1−Se2−C6 = 103.7(2)°) if the lone pairs are taken into account.…”

Section: Resultssupporting

confidence: 78%

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])

1996

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The coordination chemistry of 2,2'-dipyridyl diselenide (PySeSePy) (2) (C(10)H(8)N(2)Se(2)) has been investigated and its crystal structure has been determined (monoclinic, P2(1)/c, a = 10.129(2) Å, b = 5.7332(12) Å, c = 19.173(3) Å, beta = 101.493(8) degrees, Z = 4). In metal complexes the ligand was found to coordinate in three different modes, as also confirmed by X-ray structure determination. N,N'-coordination was found in the zinc complex [Zn(PySeSePy)Cl(2)] (3) (C(10)H(8)Cl(2)N(2)Se(2)Zn, triclinic, P&onemacr;, a = 7.9430(10) Å, b = 8.147(2) Å, c = 11.999(2) Å, alpha = 93.685(10) degrees, beta = 107.763(10) degrees, gamma = 115.440(10) degrees, Z = 2) and Se,Se'-coordination in the adduct of the ligand with bis(pentafluorophenyl)mercury(II) [PySeSePyHg(C(6)F(5))(2)] (5) (C(10)H(8)F(10)HgN(2)Se(2), monoclinic, P2(1)/n, a = 7.7325(10) Å, b = 5.9974(14) Å, c = 25.573, beta = 98.037(10) degrees, Z = 2), which however displays only weak interactions between selenium and mercury. The reaction of the ligand with norbornadiene carbonyl complexes of molybdenum and tungsten leads to reductive cleavage of the selenium-selenium bond with oxidation of the metal center and concomitant addition of the resulting selenolate to the metal carbonyl fragment. Thus the 7-coordinate complexes [Mo(SePy)(2)(CO)(3)] (6) (C(13)H(8)MoN(2)O(3)Se(2), monoclinic, P2(1)/n, a = 9.319(3) Å, b = 12.886(5) Å, c = 13.231(6) Å, beta = 109.23(3) degrees, Z = 4) and [W(SePy)(2)(CO)(3)] (7) (C(13)H(8)N(2)O(3)Se(2)W, monoclinic, P2(1)/n, a = 9.303(2) Å, b = 12.853(2) Å, c = 13.232(2) Å, beta = 109.270(10) degrees, Z = 4) were obtained. The same N,Se-coordination pattern emerges from the reaction of [Fe(2)(CO)(9)] with (2) leading to [Fe(SePy)(2)(CO)(2)] (8) (C(12)H(8)FeN(2)O(2)Se(2), monoclinic, P&onemacr;, a = 8.6691(14) Å, b = 12.443(2) Å, c = 14.085(2) Å, alpha = 105.811(10) degrees, beta = 107.533(8) degrees, gamma = 92.075(10) degrees, Z = 4).

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Section: Resultssupporting

confidence: 78%

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])

1996

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“…The conformations of di~henvldisulfides have received much experimentai (37-39) and theoretical (40)(41)(42)(43) attention. Here we take a simple view designed to rationalize the observed chemical shifts in terms of one conformation.…”

Section: Bis(2-hydroxy-ptert-butyl-5-methyl) Sulfidementioning

confidence: 99%

Conformational consequences of intramolecular hydrogen bonding by OH to the directional lone-pair of sulfur in derivatives of methyl phenyl sulfide, diphenyl sulfide, and diphenyl disulfide

Schaefer¹,

Salman²,

Wildman³

et al. 1982

Can. J. Chem.

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Complete spectral parameters for the 1H nmr spectra of 2-hydroxyphenyl methyl sulfide, 2, 2-hydroxyphenyl phenyl sulfide, 3, bis(2-hydroxy-3-tert-butyl-5-methylphenyl) sulfide, 4, and bis(2-hydroxyphenyl) disulfide, 5, are reported for CCl4 solutions at 305 K. For 2 the parameters are consistent only with a conformation in which the C—S—C plane is roughly perpendicular to the aromatic plane. The conformational determinant is the [Formula: see text] hydrogen bond which forces the mainly 3p orbital on sulfur into the benzene plane. In 3 a similar arrangement is found about the sulfur atom, with the phenyl group lying in the C—S—C plane and therefore perpendicular to the hydroxyphenyl plane (skew conformation). In 4 two [Formula: see text] hydrogen bonds exist, yielding a gable (twist) conformation. Compound 5 exists in the axial conformation with probable C2 symmetry, the CSSC dihedral angle and the CCSS torsion angles all being near 90°. For none of the compounds is there any evidence for [Formula: see text] interactions.

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“…As shown in Figure 1, the complex is a centrosymmetric dimer comprising two square-planar CuN,O, systems [Cu-N( I) 2.000 (7), Cu-N(2) 1.960 (7), Cu-O( 1) 1.967 (5), and Cu-0(3) 1.974( 6) A] linked by Cu -. -0 interactions to 0 (1) and O(1') [Cu-O(1') 2.353(5) A], which complete the squarepyramidal co-ordination.…”

mentioning

confidence: 99%

“…3.042 (7) A] where O(3) acts as the hydrogen donor. These bonds stabilise the crystal structure, which is further stabilised by a weak hydrogen bond between N(l) and C1-[3.203( 7) A] and a stacking interaction between the pyridine rings with C(5) * *…”

mentioning

confidence: 99%

Disulphide bond cleavage in a pyridine-containing disulphide–copper(II) system under aerobic conditions. X-Ray crystal structure analysis of the product, diaquabis{µ-2-[(2-pyridymethyl)-amino]ethylsulphinato-O}dicopper(II) dichloride

Odani¹,

Maruyama²,

Yamauchi³

et al. 1982

J. Chem. Soc., Chem. Commun.

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A centric organic disulfide (C-S-S-C = 180.degree.): crystal and molecular structures of chloro[bis(2-pyrimidyl) disulfide]copper(I) monohydrate and of bis(2-pyrimidyl) disulfide

Cited by 34 publications

References 3 publications

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])

Conformational consequences of intramolecular hydrogen bonding by OH to the directional lone-pair of sulfur in derivatives of methyl phenyl sulfide, diphenyl sulfide, and diphenyl disulfide

Disulphide bond cleavage in a pyridine-containing disulphide–copper(II) system under aerobic conditions. X-Ray crystal structure analysis of the product, diaquabis{µ-2-[(2-pyridymethyl)-amino]ethylsulphinato-O}dicopper(II) dichloride

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A centric organic disulfide (C-S-S-C = 180.degree.): crystal and molecular structures of chloro[bis(2-pyrimidyl) disulfide]copper(I) monohydrate and of bis(2-pyrimidyl) disulfide

Cited by 34 publications

References 3 publications

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl2], [(PySeSePy)Hg(C6F5)2], [Mo(SePy)2(CO)3], [W(SePy)2(CO)3], and [Fe(SePy)2(CO)2] (PySeSePy = C5H4NSeSeC5H4N; SePy = [C5H4N(2-Se)-N,Se])

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl2], [(PySeSePy)Hg(C6F5)2], [Mo(SePy)2(CO)3], [W(SePy)2(CO)3], and [Fe(SePy)2(CO)2] (PySeSePy = C5H4NSeSeC5H4N; SePy = [C5H4N(2-Se)-N,Se])

Conformational consequences of intramolecular hydrogen bonding by OH to the directional lone-pair of sulfur in derivatives of methyl phenyl sulfide, diphenyl sulfide, and diphenyl disulfide

Disulphide bond cleavage in a pyridine-containing disulphide–copper(II) system under aerobic conditions. X-Ray crystal structure analysis of the product, diaquabis{µ-2-[(2-pyridymethyl)-amino]ethylsulphinato-O}dicopper(II) dichloride

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Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])

Coordination Chemistry of 2,2‘-Dipyridyl Diselenide: X-ray Crystal Structures of PySeSePy, [Zn(PySeSePy)Cl₂], [(PySeSePy)Hg(C₆F₅)₂], [Mo(SePy)₂(CO)₃], [W(SePy)₂(CO)₃], and [Fe(SePy)₂(CO)₂] (PySeSePy = C₅H₄NSeSeC₅H₄N; SePy = [C₅H₄N(2-Se)-N,Se])