2,6-Bis(p-nitrophenylthiomethyl)pyridine

Sillanpää, Reijo; Kivekäs, Raikko; Escriche, Lluís; Sánchez-Castelló, G.; Teixidor, Francesç

doi:10.1107/s0108270193013617

Cited by 4 publications

(3 citation statements)

References 1 publication

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“…It is well known that 2,6-bis(arylsulfanylmethyl)pyridines, because of the orientation of the S-atom lone pairs, drastically change their conformation to bind to transition metals (Teixidor et al, 2001). The conformations of (I)-(III) seem to be unique among uncoordinated 2,6-bis(arylsulfanylmethyl)pyridines (Luo et al, 2006;Sillanpä ä et al, 1994). This is likely allowed by the presence of ortho aromatic N atoms over the pendant side chains.…”

Section: Figurementioning

confidence: 99%

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

et al. 2009

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The structure of 2,6-bis(2-pyridyltsulfanylmethyl)pyridine (pytmp), (I), C(17)H(15)N(3)S(2), presents a twisted conformation, with the three planar moieties almost perpendicular to each other. The structures of two related derivatives, namely 2,6-bis(6-methyl-2-pyridylsulfanylmethyl)pyridine (mpytmp), (II), C(19)H(19)N(3)S(2), and 2,6-bis(4-methyl-2-pyrimidylsulfanylmethyl)pyridine (mprtmp) n-pentane hemisolvate, (III), C(17)H(17)N(5)S(2).0.5C(5)H(12), present extended planar fragments with just one quasi-perpendicular arylsulfanylmethyl side arm, such that the molecules are folded in an L-shaped conformation. All three conformations appear different from those adopted by similar compounds, demonstrating the great flexibility of such species, although such differences in conformational behaviour might drive specific coordination modes.

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Section: Figurementioning

confidence: 99%

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

et al. 2009

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“…No X-ray structures of free (pro)ligands presenting the OSNSO skeleton are available for comparison. However, the structural parameters of 1•H2 may be compared with those of related compounds incorporating the characteristic aryl 2-picolyl thioether scaffold [48][49][50][51]. In particular, both CH2-S (aver.…”

Section: Scheme 2 Synthesis Of the Osnso Pro-ligand 1•h2mentioning

confidence: 99%

“…In particular, both CH2-S (aver. S1 for the list of bond lengths and angles for 1•H2) [48][49][50][51].…”

Section: Scheme 2 Synthesis Of the Osnso Pro-ligand 1•h2mentioning

confidence: 99%

Cobalt complexes of an OSNSO-tetrapodal pentadentate ligand: Synthesis, structures and reactivity

Thevenin

Daran

Poli

et al. 2021

Inorganica Chimica Acta

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The novel pentadentate tetrapodal proligand 2,6-bis [(2-hydroxyphenyl)sulfanylmethyl]pyridine (1•H2) and its cobalt(II) complex [Co(1)] (2) were synthesized and characterized by several analytical (EA, ESI-MS) and spectroscopic methods (NMR or EPR, FT-IR), including X-ray crystallography for 1•H2. Cyclic voltammetry studies showed that 2 undergoes a reversible metal-based oxidation (Co II /Co III ). Complex 2 was designed to be applied to organometallic mediated radical polymerization (OMRP), however it exhibited an extremely poor solubility in non-coordinating solvents and several vinyl monomers (styrene, vinyl acetate and tert-butyl acrylate), which hampers its potential as moderator. Complex 2 has a high affinity towards Lewis bases, such as pyridine, leading to the clean formation of the monopyridine adduct 2•py, as confirmed by X-ray crystallography. In 2•py, ligand 1 is pentacoordinated to the Co II center, with the two thioether-phenolate (S,O) moieties oriented anti to each other, and the only free coordination site of the octahedron is completed by the additional pyridine, trans to the central pyridine linker of 1. The equilibrium between 2 and 2•py could be studied by 1 H NMR. Complex 2 could be cleanly and quantitatively oxidized to its diamagnetic iodo cobalt(III) analog [Co(1)I] (3), by simple reaction with iodine. The latter could then be subjected to a halide abstraction reaction, mediated by K[B(C6F5)], affording the cationic complex [Co(1)][B(C6F5)], 4. Highlights• Cobalt(II) complexes of a bis(thioether)-bis(phenolato)-pyridyl-based OSNSO-ligand.• Neutral (OSNSO)-cobalt(III) iodide and cationic (OSNSO)-cobalt(III) complexes.• XRD, NMR, CV and EPR studies.• Evaluation in radical polymerization.

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Ruthenium(II) Complexes with NS₂ Pyridine-Based Dithia-Containing Ligands. Proposed Possible Structural Isomers and X-ray Confirmation of Their Existence

et al. 1998

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Ligands L X of the type NS2 with S-aryl and S-alkyl substituents which incorporate the unit 2,6-bis(thiomethyl)pyridine are produced. Their reaction with [RuCl2(PPh3)3] and [RuCl2(DMSO)4] produces the first reported Ru(II)/NS2 complexes. They present the general formulas [RuCl2(L X )L‘], where L‘ = PPh3 or DMSO. Several isomers are possible; however, only two have been found in each reaction. The 1H NMR spectra show that the HaHb proton atoms of the pyridine−CHaHb−thioether unit are nonisochronous. A Δδ(HaHb) value close to 1 ppm is observed for the cis complexes while this is smaller for the trans analogues. The possible distinct isomers are discussed in terms of steric effects. It is hypothesized that the trans -dl, the trans -meso, and the cis -meso-E would be the structures more favored. Those structures have been confirmed by X-ray diffraction analysis of trans -dl-[RuCl2(L1)(DMSO)]·0.5MeOH, cis-[RuCl2(L5)(PPh3)]·CH2Cl2, and trans -meso-[RuCl2(L6)(PPh3)]·1.5MeOH.

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2,6-Bis(p-nitrophenylthiomethyl)pyridine

Cited by 4 publications

References 1 publication

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

Cobalt complexes of an OSNSO-tetrapodal pentadentate ligand: Synthesis, structures and reactivity

Ruthenium(II) Complexes with NS₂ Pyridine-Based Dithia-Containing Ligands. Proposed Possible Structural Isomers and X-ray Confirmation of Their Existence

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2,6-Bis(p-nitrophenylthiomethyl)pyridine

Cited by 4 publications

References 1 publication

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

Dithioether ligands containing a 2,6-disubstituted pyridine linker with two thioether-heterocycle arms

Cobalt complexes of an OSNSO-tetrapodal pentadentate ligand: Synthesis, structures and reactivity

Ruthenium(II) Complexes with NS2 Pyridine-Based Dithia-Containing Ligands. Proposed Possible Structural Isomers and X-ray Confirmation of Their Existence

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Ruthenium(II) Complexes with NS₂ Pyridine-Based Dithia-Containing Ligands. Proposed Possible Structural Isomers and X-ray Confirmation of Their Existence