Synthesis, structure and biological activity of four new picolinohydrazonamide derivatives

2020 ◽  
Vol 76 (7) ◽  
pp. 673-680
Author(s):  
Małgorzata Szczesio ◽  
Katarzyna Gobis ◽  
Izabela Korona-Głowniak ◽  
Ida Mazerant-Politowicz ◽  
Dagmara Ziembicka ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Biological Activity ◽  
Nmr Spectroscopy ◽  
Low Temperature ◽  
Hydrogen Bonds ◽  
Essential Role ◽  
X Ray Diffraction ◽  
X Ray ◽  
Zwitterionic Form ◽  
Solvent Molecules

Four new picolinohydrazonamide derivatives, namely, 6-methyl-N′-(morpholine-4-carbonothioyl)picolinohydrazonamide, C12H17N5OS, 6-chloro-N′-(morpholine-4-carbonothioyl)picolinohydrazonamide methanol monosolvate, C11H14ClN5OS·CH3OH, 6-chloro-N′-(4-phenylpiperazine-1-carbonothioyl)picolinohydrazonamide, C17H19ClN6S, and 6-chloropicolinohydrazonamide, C6H7ClN4, have been synthesized and characterized by NMR spectroscopy and single-crystal low-temperature X-ray diffraction. In addition, their antibacterial and anti-yeast activities have been determined. The first three compounds adopt the zwitterionic form in the crystal structure regardless of the presence or absence of solvent molecules in the structure. They also adopt the same symmetry, i.e. P21/c (P21/n), unlike the fourth structure which is chiral and has the space group P212121. For all the studied cases, intermolecular N—H...O and N—H...N hydrogen bonds play an essential role in the formation of the structures.

π-Olefin-Iridium-Komplexe, XXII [1]. C-H-Aktivierung von aromatischen und aliphatischen Solvensmolekülen RH bei der Reaktion von [Cp*IrCI2]2 mit Butadienmagnesium unter Bildung von [Cp*Ir(η3-C4H7)R] sowie Kristallstruktur von [Cp*Ir(η3-C4H7)C6H5] / π-Olefin Iridium Complexes, XXII [1]. C-H Activation of Aromatic and Aliphatic Solvent Molecules RH in the Reaction of [Cp*IrCl2]2 with Butadienemagnesium with Formation of [Cp*Ir(η3-C4H7)R], and Crystal Structure of [Cp*Ir(η3-C4H7)C6H5]

1994 ◽  
Vol 49 (12) ◽  
pp. 1645-1653 ◽  
Author(s):  
Jörn Müller ◽  
Petra Escarpa Gaede ◽  
Ke Qiao
Keyword(s):  
Crystal Structure ◽  
Low Temperature ◽  
Diffraction Analysis ◽  
Iridium Complexes ◽  
X Ray Diffraction ◽  
X Ray ◽  
Nmr Spectrometry ◽  
Benzene Toluene ◽  
Solvent Molecules ◽  
Mechanism Of The Reaction

Reactions of [Cp*IrCl2]2 (Cp*=η3-C5Me5) with [MgC4H6·2 THF]n at low temperature give [Cp*Ir(η4-C4H6)] together with [Cp*Ir(η3-C4H7)R] compounds, the latter being formed via C-H activation of solvent molecules RH (RH = benzene, toluene, anisole, thiophene, furane, N-methylpyrrole, pentane, cyclohexane. THF). In the case of pyrrole, C-N -activation occurs. The ratio of syn and anti isomers of the 1-methylallyl complexes as well as the sites of C-H activation of RH were investigated by NMR spectrometry. An enantiomorphous crystal of [Cp*Ir(η3-C4H7)C6Hs] was characterized by X-ray diffraction analysis which reveals trigonal planar coordination at the Ir atom and an exo, syn conformation of the 1-methylallyl ligand. A mechanism of the reaction which involves 16-electron intermediates is discussed. The corresponding system [Cp*RhCl2]2/butadienemagnesium/RH gives only [Cp*Rh(η4-C4H6)], and no C-H activation is observed.

scholarly journals Crystal structure, synthesis and thermal properties of bis(4-benzoylpyridine-κN)bis(isothiocyanato-κN)bis(methanol-κN)iron(II)

2020 ◽  
Vol 76 (2) ◽  
pp. 276-280
Author(s):  
Carsten Wellm ◽  
Christian Näther
Keyword(s):  
Crystal Structure ◽  
Thermal Properties ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Aged Sample ◽  
X Ray Diffraction ◽  
Pure Sample ◽  
X Ray ◽  
Structure Synthesis ◽  
Solvent Molecules

In the crystal structure of the title compound, [Fe(NCS)2(C12H9NO)2(CH4O)2], the FeII cations are octahedrally coordinated by two N atoms of 4-benzoylpyridine ligands, two N atoms of two terminal isothiocyanate anions and two methanol molecules into discrete complexes that are located on centres of inversion. These complexes are linked via intermolecular O—H...O hydrogen bonds between the methanol O—H H atoms and the carbonyl O atoms of the 4-benzoylpyridine ligands, forming layers parallel to (101). Powder X-ray diffraction proved that a pure sample was obtained but that this compound is unstable and transforms into an unknown crystalline phase within several weeks. However, the solvent molecules can be removed by heating in a thermobalance, which for the aged sample as well as the title compound leads to the formation of a compound with the composition Fe(NCS)2(4-benzoylpyridine)2, which exhibits a powder pattern that is similar to that of Mn(NCS)2(4-benzoylpyridine)2.

scholarly journals Palladium(II) complexes with R2edda derived ligands, Part III: Diisobutyl (s,s)-2,2'-(1,2-ethanediyldiimino)di(4-methylpentanoate) and its palladium(II) complex: Synthesis and characterization

2009 ◽  
Vol 74 (11) ◽  
pp. 1249-1258 ◽  
Author(s):  
Bojana Zmejkovski ◽  
Goran Kaludjerovic ◽  
Santiago Gómez-Ruiz ◽  
Tibor Sabo
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Nmr Spectra ◽  
Symmetry Axis ◽  
Layer Structure ◽  
Synthesis And Characterization ◽  
X Ray Diffraction ◽  
X Ray ◽  
Ir And Nmr Spectroscopy

A new R2edda-type ester, diisobutyl (S,S)-2,2'-(1,2-ethane-diyldiimino) di(4-methylpentanoate) dihydrochloride, [(S,S)-H2iBu2eddl]Cl2, 1, and its palladium(II) complex, dichloro(diisobutyl (S,S)-2,2'-(1,2-ethanediyldiimino) di(4-methylpentanoate))palladium(II), [PdCl2{(S,S)-iBu2eddl}], 2, were synthesized and characterized by elemental analysis, as well as IR and NMR spectroscopy. It was found that complex 2 was obtained as mixture of two diastereoisomers, observed in NMR spectra. The crystal structure of compound 1 was determined by X-ray diffraction studies and is described. The isolated crystals consisted of one dicationic species [(S,S)-H2iBu2eddl]2+ and two Cl-. The crystal system was tetragonal with the space group P42. Hydrogen bonds significant for the manner of packing are N-H1N???Cl, 3.049(3) ?, 159(3)? and N-H2N???Cl, 3.100(3) ?, 164(3)?. An infinite chain was formed building a one layer structure, usual for these types of compounds. The C2 symmetry axis of the compound passes through the C1-C1i bond vector and lies perpendicular to the plane N2Cl2.

Two new organic-selenate salts: syntheses and crystal structures of bis(di-iso-propylammonium) selenate and di-n-butylammonium hydrogenoselenate

2017 ◽  
Vol 72 (6) ◽  
pp. 425-432
Author(s):  
Waly Diallo ◽  
Libasse Diop ◽  
Cheikh Abdoul Khadir Diop ◽  
Laurent Plasseraud ◽  
Hélène Cattey
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Elemental Analysis ◽  
X Ray Diffraction ◽  
Monoclinic System ◽  
Space Group ◽  
X Ray ◽  
Structural Characterizations

AbstractTwo new dialkyammonium selenate salts [i-Pr2NH2]2[SeO4] (1) and [n-Bu2NH2][HSeO4] (2) have been isolated and characterized by single-crystal X-ray diffraction. Salt 1 crystallizes in the monoclinic system, space group P21/n with a=8.7190(5), b=8.8500(4), c=22.5953(9) Å, β=94.6290(17)°, V=1737.84(14) Å3 and Z=4. Salt 2 crystallizes in the monoclinic system space group P21/n with a=10.9328(9), b=8.1700(6), c=13.8095(11) Å, β=97.130(3)°, V=1223.94(17) Å3 and Z=4. In both salts, dialkylammonium cations and selenate anions are connected through NH···O and OH···O hydrogen bonds. In the crystal structure, 1 and 2 are organized in layer-like arrangements. Structural characterizations were completed by infrared and 1H, 13C{1H} and 77Se NMR spectroscopy and elemental analysis which corroborate the X-ray elucidations.

Crystal structure of phenanthrenide salts stabilized by 15-crown-5 and 18-crown-6

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Natalie Eichstaedt ◽  
Kasper P. van der Zwan ◽  
Lina Mayr ◽  
Renée Siegel ◽  
Jürgen Senker ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Nmr Spectroscopy ◽  
Coordination Number ◽  
Solid State Nmr ◽  
Inert Atmosphere ◽  
Potassium Cation ◽  
X Ray Diffraction ◽  
X Ray ◽  
Solvent Molecules

Abstract Potassium 15-crown-5 phenanthrenide and potassium 18-crown-6 phenanthrenide were synthesized and characterized by powder X-ray diffraction and 39K solid state NMR spectroscopy. While the radical carbanion is very reactive in solution, the crystals are stable and storable under inert atmosphere. For 15-crown-5, a sandwich-like complex of potassium is formed with two molecules of crown ether per potassium resulting in a coordination number of 10. For the larger 18-crown-6 ligand, a 1:1 complex is obtained and a coordination number of 6 for the potassium cation. In neither crystal structure solvent molecules are incorporated. The 15-crown-5 compound crystallizes faster and is less soluble in THF as compared to the 18-crown-6 compound. Both compounds form solid phenanthrenide that is easy to handle and can be applied for reduction reactions.

Model compounds of aromatic nylons. 3. The conformation of the 4T Nylon, poly(tetramethylene terephthalamide), using X-ray diffraction, solid-state 13C nmr spectroscopy and ir spectroscopy

1989 ◽  
Vol 67 (5) ◽  
pp. 840-849 ◽  
Author(s):  
Josée Brisson ◽  
Johanne Gagné ◽  
François Brisse
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Solid State Nmr ◽  
13C Nmr Spectroscopy ◽  
X Ray Diffraction ◽  
Model Compounds ◽  
X Ray ◽  
Structure Determinations

Three model compounds of poly(tetramethylene terephthalamide) or 4T Nylon have been synthesized and characterized using single crystal X-ray diffractometry, infrared spectroscopy, and 13CCP/MAS nmr spectroscopy. The model compounds are the para-substituted N,N′-tetramethylene dibenzamides, where the substituents are the—OMe, —tBu, —CN, and —CH3 groups. The crystal structure determinations reveal three distinct conformations for the CO—NH—(CH2)4—NH—CO sequence of atoms. The conformation is all trans for OMe, tgtttg−t for the tBu substituent, and tsttts−t for the CN substituent ([Formula: see text], [Formula: see text], and [Formula: see text]). In all three derivatives, the dihedral angle between the aromatic ring and the amide plane is around 30°. The OMe and tBu para-substituted molecules are interconnected by nearly linear hydrogen bonds of normal N … O distances. However, for the CN derivative the N … O distance is exceptionally short, 2.402(4) Å. On the basis of its infrared and solid state nmr spectra, it is proposed that N,N′-tetramethylene di-para-methyl benzamide has a crystal structure comparable to that of its unsubstituted analog. The methylenic sequence of the parent polyamide, 4T Nylon, has the tgtttg−t conformation. Furthermore, the polyamide chains form sheets within which the chains, parallel to one another, are connected through hydrogen bonds. Keywords: polyamide, crystal structure, solid-state nmr.

scholarly journals Exploring the Structural Chemistry of Pyrophosphoramides: N,N′,N″,N‴-Tetraisopropylpyrophosphoramide

Chemistry ◽  
2021 ◽  
Vol 3 (1) ◽  
pp. 149-163
Author(s):  
Duncan Micallef ◽  
Liana Vella-Zarb ◽  
Ulrich Baisch
Keyword(s):  
Crystal Structure ◽  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
Room Temperature ◽  
Intermolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
X Ray

N,N′,N″,N‴-Tetraisopropylpyrophosphoramide 1 is a pyrophosphoramide with documented butyrylcholinesterase inhibition, a property shared with the more widely studied octamethylphosphoramide (Schradan). Unlike Schradan, 1 is a solid at room temperature making it one of a few known pyrophosphoramide solids. The crystal structure of 1 was determined by single-crystal X-ray diffraction and compared with that of other previously described solid pyrophosphoramides. The pyrophosphoramide discussed in this study was synthesised by reacting iso-propyl amine with pyrophosphoryl tetrachloride under anhydrous conditions. A unique supramolecular motif was observed when compared with previously published pyrophosphoramide structures having two different intermolecular hydrogen bonding synthons. Furthermore, the potential of a wider variety of supramolecular structures in which similar pyrophosphoramides can crystallise was recognised. Proton (1H) and Phosphorus 31 (31P) Nuclear Magnetic Resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS) were carried out to complete the analysis of the compound.

scholarly journals Crystal structure of 3-benzyl-2-[(E)-2-(furan-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one and 3-benzyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-2,3-dihydroquinazolin-4(1H)-one from synchrotron X-ray diffraction

2018 ◽  
Vol 74 (1) ◽  
pp. 10-14
Author(s):  
Flavien A. A. Toze ◽  
Vladimir P. Zaytsev ◽  
Lala V. Chervyakova ◽  
Elisaveta A. Kvyatkovskaya ◽  
Pavel V. Dorovatovskii ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Axial Position ◽  
Isatoic Anhydride ◽  
X Ray Diffraction ◽  
X Ray ◽  
Bond Angles ◽  
Pyramidal Geometry ◽  
Three Component Reaction ◽  
Racemic Crystals

The chiral title compounds, C21H18N2O2, (I), and C21H18N2OS, (II) – products of the three-component reaction between benzylamine, isatoic anhydride and furyl- or thienyl-acrolein – are isostructural and form isomorphous racemic crystals. The tetrahydropyrimidine ring in (I) and (II) adopts a sofa conformation. The amino N atom has a trigonal–pyramidal geometry [sum of the bond angles is 347.0° for both (I) and (II)], whereas the amido N atom is flat [sum of the bond angles is 359.3° for both (I) and (II)]. The furyl- and thienylethenyl substituents in (I) and (II) are planar and the conformation about the bridging C=C bond isE. These bulky fragments occupy the axial position at the quaternary C atom of the tetrahydropyrimidine ring, apparently, due to steric reasons. In the crystals, molecules of (I) and (II) form hydrogen-bonded helicoidal chains propagating along [010] by strong intermolecular N—H...O hydrogen bonds.

Synthesis, crystal structure and molecular conformation of (±)-1-oxoferruginol and (±)-shonanol

2004 ◽  
Vol 219 (10) ◽  
Author(s):  
Swastik Mondal ◽  
Monika Mukherjee ◽  
Arnab Roy ◽  
Debabrata Mukherjee
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Diffraction Data ◽  
Molecular Conformation ◽  
Membered Ring ◽  
Methyl Groups ◽  
Single Bond ◽  
X Ray Diffraction ◽  
X Ray ◽  
Chemical Structures

Abstract(±)-1-oxoferruginol and (±)-shonanol, two potential intermediates in the synthesis of tricyclic diterpenoid ferruginol, have been prepared and crystal structures of the compounds have been investigated using single-crystal X-ray diffraction data. The methyl groups of the isopropyl moiety in (±)-shonanol are disordered over two positions with occupation factors 0.65(1) and 0.35(1), respectively. Although the chemical structures of two compounds are very similar, a C—C single bond in the terminal six-membered ring of (±)-1-oxoferruginol is replaced by a C=C bond in (±)-shonanol, the quantitative isostructurality index calculations indicate that the structures are not isostructural. Intermolecular O—H…O hydrogen bonds between pairs of molecules in the compounds related by center of inversion lead to characteristic dimers forming R

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