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Chumakov, Yu. M.; Antosyak, B. Ya.; Mazus, M. D.; Tsapkov, V. I.; Samus, N. M.

doi:10.1023/a:1004843109755

Cited by 12 publications

(15 citation statements)

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“…[32] Solidstate structures, inferred from X-ray data, reveal a complex and rather confusing situation. For instance, Chumakov et al [33] found that at 292 K the unit cell of compound 14 contains two tautomeric molecules with imine and enamine forms, respectively. However, Cungen et al [34] could only locate the enamine form at 298 K, a result further corroborated by Büyükgüngör and co-workers [35] at 208 K. The structures of a series of Schiff bases generated from TRIS and salicylaldehydes bearing different substituents -5-nitro- (15) [36] and 3-hydroxy-(16) at 223 K, [35] 3-methoxy-(17) at 213 K, [35] and 5-phenylazo-(18) [37] -were all determined to be enamine tautomers in the solid state.…”

Section: Introductionmentioning

confidence: 99%

“…However, Cungen et al [34] could only locate the enamine form at 298 K, a result further corroborated by Büyükgüngör and co-workers [35] at 208 K. The structures of a series of Schiff bases generated from TRIS and salicylaldehydes bearing different substituents -5-nitro- (15) [36] and 3-hydroxy-(16) at 223 K, [35] 3-methoxy-(17) at 213 K, [35] and 5-phenylazo-(18) [37] -were all determined to be enamine tautomers in the solid state. In the cases of the halogenated derivatives 19 [33] and 20, [36] the unit cell contains two molecules at 293 K, although both exhibit an enamine structure.…”

Section: Introductionmentioning

confidence: 99%

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Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Martínez¹,

Авалос²,

Babiano³

et al. 2011

Eur J Org Chem

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Three Schiff bases generated by conventional condensation of a simple aminopolyol (TRIS) and 5‐bromo‐ and 5‐iodosalicylaldehyde, and 2‐hydroxy‐1‐naphthaldehyde, have been fully characterized, both in solution and in the solid state. This study provides a complete analysis of imine–enamine equilibria, and sheds light onto the mechanism of hydrogen transfer, which has been controversial in the literature. Low‐temperature X‐ray diffraction accompanied by electron‐density maps have further been complemented by theoretical studies at the B3LYP/6‐31G* and M06‐2X/6‐311++G** levels. To ascertain the influence of crystal packing on tautomeric stability, the lattice has also been simulated by computation. This protocol involves the assessment of a supramolecular cluster around a core tautomer possessing either imine or enamine structures. Such an analysis, in full agreement with solid‐state data, reveals the greater stability of zwitterionic structures for the salicyl derivatives. In contrast, these substances show preferential imine forms in solution, whereas the naphthyl‐based compound exhibits a prevalent keto‐enamine structure in all cases.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Martínez¹,

Авалос²,

Babiano³

et al. 2011

Eur J Org Chem

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“…However, according to [5], these distances exceed the maximum possible length of the Cu···O coordination bond (3.07 Å) and thus cannot be regarded as coordination bonds. The TBP apices for the Cu (12) (2) Cu (1) [7], and 3-hydroxypropylsalicylaldiminatocopper [8], the analogous dihedral angle is 20.6°, 14.9°, and 22.7°, respectively. However, such a folding is absent from nitrato-2-(2-hydroxyethyliminomethyl)phenolocopper [9], nitrato-2-(2-hydroxyethyliminomethyl)phenolo-4-picolinecopper [10], and 2-(2-hydroxyethyliminomethyl)phenolocopper [11].…”

Section: Resultsmentioning

confidence: 99%

“…The starting 2-(2-hydroxybenzylideneamino)-2-hydroxymethylpropane-1,3-diol (HL) and 2-hydroxymethyl-2-(2-hydroxy-5-nitrobenzylideneamino)propane-1,3-diol (HL 1 ) were prepared as described in [2].…”

Section: Methodsmentioning

confidence: 99%

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Coordination Compounds of Copper(II) Nitrate with Products of Aminotris(hydroxymethyl)methane Condensation with Salicyl- and 5-Nitrosalicylaldehydes: Synthesis and Crystal Structures

et al. 2005

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Earlier [1], 3 d -element salts were found to react with the products of aminotris(hydroxymethyl)methane condensation with salicylaldehyde or its derivatives to give a variety of coordination compounds with fungicidal properties. Depending on the synthesis conditions and the nature of the starting reagents, mono-or polynuclear complexes can be obtained. Because only halides and acetates were used as starting salts, it was interesting to find out how the compositions and structures of the resulting coordination compounds would be affected by replacement of the above acid residues by the nitrate ion. In connection with this, we synthe-II ) and determined their crystal structures by X-ray diffraction analysis N OH HO HO OH N OH HO HO OH O 2 N ; (HL) (HL 1 )Abstract -The crystal structures of copper(II) nitrate complexes with 2-(2-hydroxybenzylideneamino)-2-hydroxymethylpropane-1,3-diol (HL) and 2-hydroxymethyl-2-(2-hydroxy-5-nitrobenzylideneamino)propane-1,3-diol (HL 1 ) were determined. The resulting complexes were formulated as [II ). The crystals of I are monoclinic, a = 17.809(4) Å, b = 30.549(6) Å, c = 18.962(4) Å, β = 115.36(3) ° , space group Cc , Z = 8, R = 0.0482. Complex I is composed of two independent three-dimensional µ 3 -oxo complexes; the coordination polyhedron of the copper atoms in both compounds is an elongated tetragonal bipyramid. The coordination polyhedron of the third Cu atom is a tetragonal pyramid. The bases of the pyramids are composed of the oxygen atoms of the phenol and alcohol OH groups, the imine N atom of ligand L, and µ 3 -oxo atoms. The phenol and water O atoms serve as the apices in both the tetragonal bipyramids. The crystals of II are triclinic, a = 6.062(1) Å, b = 7.701(2) Å, c = 16.162(3) Å, α = 88.15(3) ° , β = 84.94(3) ° , γ = 78.13(3) ° , space group P , Z = 2, R = 0.0272. Complex II is composed of polymer chains formed by coordination bonds between the copper atom and two O atoms of the amino alcohol in the azomethine of the neighboring complex connected to the initial one by translation along the x axis. These chains are linked through hydrogen bonds involving the oxygen atoms of the NO 2 groups. The benzene rings of the azomethine ligands of the adjoining complexes from different chains are antiparallel to each other. The coordination polyhedron of the central atom is an elongated tetragonal bipyramid. Its equatorial plane is formed by the phenol O atom, one of the alcohol O atoms, the N atom of ligand L 1 , and the O atom of the amino alcohol in the neighboring complex. The apices are the O atom of the water molecule and the O atom of the amino alcohol in the neighboring azomethine molecule. In complexes I and II , the outer-sphere nitrato group mainly serves to unite trimers and polymers in the crystal by means of hydrogen bonds.

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Synthesis, structural and corrosion inhibition studies on cobalt(II), nickel(II), copper(II) and zinc(II) complexes with 2-acetylthiophene benzoylhydrazone

Singh

2011

Inorganica Chimica Acta

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Cited by 12 publications

References 1 publication

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Coordination Compounds of Copper(II) Nitrate with Products of Aminotris(hydroxymethyl)methane Condensation with Salicyl- and 5-Nitrosalicylaldehydes: Synthesis and Crystal Structures

Synthesis, structural and corrosion inhibition studies on cobalt(II), nickel(II), copper(II) and zinc(II) complexes with 2-acetylthiophene benzoylhydrazone

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