Zwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2<i>H</i>-pyran-4-olate monohydrate

Djedouani, Amel; Boufas, Sihem; Allain, Magali; Bouet, Gilles; Khan, Mustayeen A.

doi:10.1107/s1600536808026032

Cited by 4 publications

(3 citation statements)

References 14 publications

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“…The H atom attached to N was located in a difference-Fourier map and freely refined. The resulting iminium and hydroxyl groups are linked by an intramolecular N-H…O hydrogen bond [0.90, 1.091 and 0.880 Å] for L1, L2 and L3 respectively, comparable with the similar zwitterions in the literature[35,36]. The bond distances shown in Table2indicate that the C-…”

supporting

confidence: 59%

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Boulemche

Anak

Djedouani

et al. 2019

Journal of Molecular Structure

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Three new Schiff bases compounds (L1-L2-L3) were synthesized by a condensation reaction in 1:1 molar ratios of dehydroacetic acid (3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione) and 4-fluoro/4chloro/4-bromo aniline in ethanol, the products were obtained in excellent yields. Their structures were characterized by spectroscopic techniques (FT-IR and 1H-NMR) and single-crystal X-ray diffraction. The three compounds display zwitterionic forms, with cationic iminium and anionic enolate groups.The aromatic ring and dehydroacetic acid ring are in a trans position with respect to the C=N bond. Calculations in the framework of the density-functional theory (DFT) were carried out to determine the optimized structures and electronic properties as the HOMO-LUMO energy gap.Hirshfeld surface analysis was used to support the packed crystal lattice 3D network intermolecular forces. The NH form is found to be more stable than OH form. On the other hand, the in situ generated copper (II) complexes were examined for their catalytic activities and were found to catalyze the oxidation reaction of catechol to o-quinone under atmospheric dioxygen. The present study reveals that the rate of oxidation depends on the nature of the substituents in the phenyl ring, the counter anion and the concentration of ligand. The combination L1(Cu(CH3COO)2) gives the highest rate.

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confidence: 59%

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Boulemche

Anak

Djedouani

et al. 2019

Journal of Molecular Structure

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“…For proton-transfer processes, see: Lussier et al (1987). For Schiff base structures, see: Djedouani et al (2007Djedouani et al ( , 2008. For Schiff base bond lengths and angles, see: ; ; Bai & Jing (2007 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…As part of our ongoing studies of Schiff bases (Djedouani et al, 2007(Djedouani et al, , 2008, we now describe the synthesis and the structure of the title compound, which takes the form phenol-imine and complete a six-membered pseudocycle via an…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of (E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one

Djedouani¹,

Boufas

Cleymand

et al. 2015

Acta Cryst E

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In the title Schiff base, C14H13NO4, which adopts the phenol–imine tautomeric form, the dihedral angle between the planes of the benzene and heterocyclic (r.m.s. deviation = 0.037 Å) rings is 53.31 (11)°. An intramolecular O—H⋯N hydrogen bond closes an S(6) ring. In the crystal, molecules are linked by O—H⋯O hydrogen bonds to generate C(11) chains propagating in the [010] direction. A weak C—H⋯O link is also observed, leading to the formation of R 5 5(32) rings extending parallel to the (101) plane.

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Bis{(E)-3-[(diethylmethylammonio)methyl]-N-[3-(N,N-dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium} tetraiodide pentahydrate

et al. 2009

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The title compound, 2C21H34N4O3S2+·4I−·5H2O, was prepared exclusively as the E isomer by methylation of the corresponding N-phenylpyridin-4-amine. There are two symmetry-independent molecules in the asymmetric unit with no significant differences in bond lengths and angles. The aromatic rings are not coplanar with the pyridin-4-imine groups, as indicated by the C—N—C—C torsion angles of 47.7 (7) and 132.6 (5)°.

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Zwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate

Cited by 4 publications

References 14 publications

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Synthesis, X-ray crystallography, computational studies and catecholase activity of new zwitterionic Schiff base derivatives

Crystal structure of (E)-4-hydroxy-3-{1-[(4-hydroxyphenyl)imino]ethyl}-6-methyl-2H-pyran-2-one

Bis{(E)-3-[(diethylmethylammonio)methyl]-N-[3-(N,N-dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium} tetraiodide pentahydrate

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