Crystal structure and spectroscopic properties of (E)-1,3-dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole

The title compound (E)-1,3-dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole, C11H12N6O2, has monoclinic (C2/c) symmetry at 100 K. This triazene derivative was synthesized by the coupling reaction of 1,3-dimethylimidazolium iodide with 1-azido-4-nitro benzene in the presence of sodium hydride (60% in mineral oil) and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule consists of six-membered and five-membered rings, which are connected by a triazene moiety (–N=N—N–). In the solid-state, the molecule is found to be planar due to conjugation throughout the molecule. The extended structure shows two layers of molecules, which present weak intermolecular interactions that facilitate the stacked arrangement of the molecules forming the extended structure. Furthermore, there are several weak pseudo-cyclical interactions between the nitro oxygen atoms and symmetry-adjacent H atoms, which help to arrange the molecules.

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3-pyridiniumindolyl-2-thiolates - New type of functionalized indoles

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19881761 ◽

1988 ◽

Vol 53 (8) ◽

pp. 1761-1769 ◽

Cited By ~ 6

Author(s):

Jozef Gonda ◽

Pavol Kristian

Keyword(s):

Diffraction Analysis ◽

Dimethyl Sulfoxide ◽

Mass Spectra ◽

Sodium Ethoxide ◽

Sodium Hydride ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

New Type ◽

C Nmr

2-Bromomethylphenyl isothiocyanate (I) reacts with pyridines to give 2-isothiocyanatobenzylpyridinium bromides II. Deprotonation of these compounds with sodium ethoxide in ethanol of sodium hydride in dimethyl sulfoxide afforded novel type of functionalized indoles, 3-pyridiniumindolyl-2-thiolates. Reaction of II with KOH or KCN gave products of addition to the NCS group VII and VIII, respectively. Structure of the obtained compounds was proven by IR, 1H NMR, 13C NMR, and mass spectra and was confirmed by X-ray diffraction analysis of 3-pyridiniumindolyl-2-thiolate.

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A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation

RSC Advances ◽

10.1039/c9ra01370a ◽

2019 ◽

Vol 9 (36) ◽

pp. 20505-20512 ◽

Cited By ~ 1

Author(s):

Mixia Hu ◽

YaLi Yan ◽

Baohua Zhu ◽

Fei Chang ◽

Shiyong Yu ◽

...

Keyword(s):

Carbon Monoxide ◽

Biological Activity ◽

Activated Carbon ◽

Fluorescence Spectroscopy ◽

Single Crystal ◽

Structural Characterization ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

C Nmr

Five Mn(i) photo-activated carbon monoxide-releasing molecules were synthesized by reactions of MnBr(CO)5 with L1–L4, and characterized via single crystal X-ray diffraction, 1H-NMR, 13C-NMR, IR, UV-vis and fluorescence spectroscopy.

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Microbial Transformation of Glycyrrhetinic Acid by Colletotrichum lini AS3.4486

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.1120-1121.877 ◽

2015 ◽

Vol 1120-1121 ◽

pp. 877-881

Author(s):

Chao Jun He ◽

Yu Min Yang ◽

Kong Yang Wu

Keyword(s):

Single Crystal ◽

Microbial Transformation ◽

Glycyrrhetinic Acid ◽

Conversion Product ◽

X Ray Diffraction ◽

Orthorhombic Space Group ◽

X Ray ◽

H Nmr ◽

Sole Product ◽

C Nmr

The biotransformation of 18β-glycyrrhetinic acid by Colletotrichum lini AS3.4486 was investigated. The conversion reaction was carried out for 72h, and the sole product was isolated by column chromatography and elucidated as 7β,15α-dihydroxy-18β-glycyrrhetinic acid by HR-ESI-MS, 1H-NMR , 13C-NMR and single–crystal X-ray diffraction. The crystal of the conversion product belongs to orthorhombic, space group P212121 with 11.828(1), 13.213(2), 19.606(2) Å , V = 3064.0 Å3, Z = 4. This study povides a new method for the synthesis of 7β,15α-dihydroxy-18β-glycyrrhetinic acid.

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β-Hydroxydithiozimtsäurederivate als Liganden. Synthese und Charakterisierung neuartiger 1,1-Ethendithiolato- und O,S-Chelatkomplexe / Derivatives of β -Hydroxydithiocinnamic Acids as Ligands. Syntheses and Characterisation of Novel 1,1-Ethenedithiolato and O,S-Chelate Complexes

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0323 ◽

2007 ◽

Vol 62 (3) ◽

pp. 475-482 ◽

Cited By ~ 7

Author(s):

Karsten Schubert ◽

Helmar Görls ◽

Wolfgang Weigand

Keyword(s):

Bidentate Ligand ◽

Molecular Structures ◽

X Ray Diffraction ◽

Chelate Complexes ◽

X Ray ◽

H Nmr ◽

Hexyl Ester ◽

Elemental Analyses ◽

Derivatives Of ◽

C Nmr

Starting from 4-bromoacetophenone 1, the 4-bromo-β -hydroxydithiocinnamic acid 2 and the 4-bromo-β -hydroxydithiocinnamic acid hexyl ester 3 were prepared using carbon disulfide and potassium-tert-butylate as a base. Acting as a ligand, the acid gives 1,1-ethenedithiolato complexes with (Ph3P)2Pt(II) (4a), (Et3P)2Pt(II) (4b), dppePt(II) (4c), (Ph3P)2Pd(II) (4d), dppePd(II) (4e), and dppeNi(II) (4f). In contrast to the acid, the deprotonated ester 3 forms a monoanionic bidentate ligand. [O,S] Complexes of Pt(II) (5a), Pd(II) (5b) and Ni(II) (5c) were obtained. All complexes have been fully characterised using 1H NMR, 13C NMR and 31P NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analyses. The molecular structures of the complexes 4b and 5a - 5c were determined by X-ray diffraction analyses.

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Synthesis and characterization of a new bis-NHC palladium complex and its catalytic activity in the Mizoroki–Heck reaction

Journal of Chemical Research ◽

10.1177/1747519820917883 ◽

2020 ◽

Vol 44 (11-12) ◽

pp. 684-688

Author(s):

Can Feng ◽

Cheng-xin Liu ◽

Yu-fang Wang ◽

Jin Cui ◽

Ming-jie Zhang

Keyword(s):

Palladium Complex ◽

Coupling Reaction ◽

Aryl Halides ◽

Heck Coupling ◽

X Ray ◽

X Ray Crystallography ◽

H Nmr ◽

Excellent Stability ◽

C Nmr

A new bis- N-heterocyclic carbene palladium complex, (C13H9N2F2)2PdCl2, is synthesized by a three-step reaction and characterized by 1H NMR and 13C NMR spectroscopy as well as by X-ray crystallography. This new bis- N-heterocyclic carbene palladium complex has excellent stability and is capable of efficiently catalyzing the Mizoroki–Heck coupling reaction of aryl halides with acrylates.

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On Attempts to Synthesize Lanthanide Complexes of the Dianionic Fluorenyl-alkoxo Ligand [C13H8-cyclo-C6H10-O]2-. Crystal Structure of (C13H9-cyclo-C6H10-O)LaI2(DME)2

Zeitschrift für Naturforschung B ◽

10.1515/znb-2003-0506 ◽

2003 ◽

Vol 58 (5) ◽

pp. 389-394 ◽

Cited By ~ 2

Author(s):

Alexander A. Trifonov ◽

Mikhail N. Bochkarev ◽

Herbert Schumann ◽

Sebastian Dechert

Keyword(s):

Molecular Structure ◽

Crystal Structure ◽

Ir Spectra ◽

Single Crystal ◽

Lanthanide Complexes ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

Elemental Analyses ◽

C Nmr

Racemic trans-2-(9(H)-fluoren-9-yl)cyclohexanol, C13H9-cyclo-C6H10-OH (1), reacts with two equivalents of potassium naphthalenide in THF to give the dipotassium salt [C13H8-cyclo-C6H10-O]- K2(THF) (2). Recrystallization of 2 from pyridine affords the solvent free salt [C13H8-cyclo-C6H10- O]K2 (3). The reactions of LaI3(THF)4 with one equivalent of 2 or of YbI2(THF)2 with equimolar amounts of 2 produce the alkoxolanthanum diiodide (C13H9-cyclo-C6H10-O)LaI2(DME)2 (4) and the ytterbium dialkoxide (C13H9-cyclo-C6H10-O)2Yb(THF)0.5(5), respectively. [(Me3Si)2N]3Y reacts with three equivalents of 1 with elimination of hexamethyldisilazane and formation of the yttrium trialkoxide (C13H9-cyclo-C6H10-O)3Y (6). The compounds 2 to 5 were characterized by elemental analyses, 1H NMR, 13C NMR and IR spectra. The molecular structure of 4 was determined by single crystal X-ray diffraction.

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Synthesis and characterization of novel azo-embedded N-confused tetraphenylporphyrin

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424609000292 ◽

2009 ◽

Vol 13 (02) ◽

pp. 215-222 ◽

Cited By ~ 9

Author(s):

Motoki Toganoh ◽

Takayoshi Hihara ◽

Kentaro Yonekura ◽

Yuichi Ishikawa ◽

Hiroyuki Furuta

Keyword(s):

Absorption Spectrum ◽

Effective Interaction ◽

Coupling Reaction ◽

Crystallographic Analysis ◽

Synthesis And Characterization ◽

X Ray ◽

H Nmr ◽

Cis Isomer ◽

C Nmr

A unique class of azo porphyrin, 5,10,15,20-tetraphenyl-21-phenylazo-(2-aza-21-carbaporphyrin 1, in which an azophenyl group is embedded in N -confused porphyrin, was synthesized and characterized by 1 H NMR, 13 C NMR, UV-vis absorption, MS, and X-ray crystallographic analysis. Synthesis of 1 was achieved through a coupling reaction of 21-amino N -confused tetraphenylporphyrin with nitrosobenzene and subsequent deoxygenation of resulting azoxy derivative with a trioxo rhenium(VII) N -fused porphyrinato catalyst. The azo-conjugate molecule was exclusively obtained as a trans-isomer and no isomerization to the cis-isomer was observed under thermal or photoirradiation. The absorption spectrum of 1 shows a moderate red-shift due to the effective interaction between the porphyrinic π-system and the connecting azophenyl group. Upon protonation, this effect is essentially lost as a result of removing degeneracy of LUMO and LUMO+1.

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Stereochemistry of the Bucherer–Bergs and Strecker reactions of tropinone, cis-bicyclo[3.3.0]octan-3-one and cis-3,4-dimethylcyclopentanone

Canadian Journal of Chemistry ◽

10.1139/v79-238 ◽

1979 ◽

Vol 57 (12) ◽

pp. 1456-1461 ◽

Cited By ~ 16

Author(s):

Gregorio G. Trigo ◽

Carmen Avendaño ◽

Emilia Santos ◽

John T. Edward ◽

Sin Cheong Wong

Keyword(s):

Carbonyl Group ◽

Equatorial Position ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

Strecker Reaction ◽

C Nmr

The tropane-3-spiro-5′-hydantoin (α isomer) obtained from tropinone by the Bucherer–Bergs reaction has been shown by 13C nmr and X-ray diffraction studies to have the 4′-carbonyl group in the equatorial position; the β isomer, obtained via the Strecker reaction, has this group axial. The results of these two reactions on cis-bicyclo[3.3.0]octan-3-one and on cis-3,4-dimethylcyclopentanone show, on the basis of the 1H nmr, 13C nmr, and X-ray diffraction studies of the products, a stereochemical course related to the preferred conformation of the cyclopentane rings.

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Efficient continuous flow-synthesis of novel spiro-naphthalene-1,2'-[1,3,4]oxadiazol-4-ones

10.3762/bxiv.2021.89.v1 ◽

2021 ◽

Author(s):

Lange Yakubu Saleh ◽

Bahadır Altıntaş ◽

Layla Filiciotto ◽

Yunus Zorlu ◽

Rafael Luque ◽

...

Keyword(s):

Quantum Chemical ◽

Cycloaddition Reaction ◽

Synthesis Methods ◽

X Ray Diffraction ◽

Flow Synthesis ◽

X Ray ◽

H Nmr ◽

Experimental Findings ◽

Hydrazonyl Chlorides ◽

C Nmr

The highly efficient cycloaddition reaction of hydrazonyl chlorides with 2,3-dichloro-1,4-naphthoquinone yielded pharmaceutically important spiro-naphthalene-1,2'-[1,3,4]oxadiazol-4-ones with moderate to good yields under batch and flow synthesis methods. The obtained products were elucidated by IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction technique (only for 6h). The synthesized molecules have been subjected to theoretical analysis by quantum chemical calculations at B3LYP/6-31G(d,p) level, which provided supporting data for the experimental findings.

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Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989021000864 ◽

2021 ◽

Vol 77 (2) ◽

pp. 184-189

Author(s):

Cong Nguyen Tien ◽

Trung Vu Quoc ◽

Dat Nguyen Dang ◽

Giang Le Duc ◽

Luc Van Meervelt

Keyword(s):

Title Compound ◽

Crystal Packing ◽

Asymmetric Unit ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

Hydrogen Bonding Interactions ◽

Hirshfeld Analysis ◽

Phenyl Rings ◽

C Nmr

The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-methoxyphenyl)-2-chloroacetamide and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one, which was obtained from the reaction of 4-hydroxybenzaldehyde and acetophenone. The structure of the title compound was determined by IR, 1H-NMR, 13C-NMR and HR–MS spectroscopic data and further characterized by single-crystal X-ray diffraction. The asymmetric unit contains four molecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each molecule varies between 14.9 (2) and 45.8 (2)°. In the crystal, C—H...O hydrogen-bonding interactions link the molecules into chains running along the [001] direction. In addition, C—H...π interactions further stabilize the crystal packing. A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from H...H (43.6%), C...H/H...C (32.1%) and O...H/H...O (18.1%) interactions.

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