scholarly journals Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C-F…H-C bond

2019 ◽  
Author(s):  
Vuyisa Mzozoyana ◽  
Fanie R van Heerden ◽  
Craig Grimmer
Keyword(s):  
Single Crystal ◽  
Phenyl Ring ◽  
Fluorine Atom ◽  
Nmr Spectra ◽  
Intramolecular Interaction ◽  
X Ray ◽  
Solution State ◽  
H Nmr ◽  
Mild Conditions ◽  
C Nmr

4-(2-fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three step-reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13C NMR suggested that this C-F…H-C coupling is a through-space interaction. The 2‑D HOESY spectrum and 1H‑{19F} 1‑D spectrum were also done to confirm this F…H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favours the orientation with the fluorine atom is closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C-F…H-C interactions.

scholarly journals Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

2020 ◽  
Vol 16 ◽  
pp. 190-199
Author(s):  
Vuyisa Mzozoyana ◽  
Fanie R van Heerden ◽  
Craig Grimmer
Keyword(s):  
Single Crystal ◽  
Phenyl Ring ◽  
Fluorine Atom ◽  
Nmr Spectra ◽  
Intramolecular Interaction ◽  
X Ray ◽  
Solution State ◽  
H Nmr ◽  
Mild Conditions ◽  
C Nmr

4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C–F···H–C interaction.

Bis[dicarbonyl(cyclopentadienyl)ruthenium(I)] Komplexe / Bis[dicarbonyl(cyclopentadienyl)ruthenium(I)] Complexes

2002 ◽  
Vol 57 (9) ◽  
pp. 1017-1026 ◽  
Author(s):  
Herbert Schumann ◽  
Susanne Stenz ◽  
Frank Girgsdies ◽  
Stefan H. Mühle
Keyword(s):  
Single Crystal ◽  
Nmr Spectra ◽  
X Ray ◽  
Tert Butyl ◽  
New Compounds ◽  
C Nmr

Ru3(CO)12 reacts with 1-tert-butyl-2,4-cyclopentadiene (1), 1-trimethylsilyl-2,4-cyclopentadiene (2), 1-tert-butyl-3-methyl-2,4-cyclopentadiene (3), 1,3-di(tert-butyl)-2,4-cyclopentadiene (4), 1-iso-propyl-2,3,4,5-tetramethyl-2,4-cyclopentadiene (5), 1-tert-butyl-2,3,4,5-tetramethyl- 2,4-cyclopentadiene (6), 1-phenyl-2,3,4,5-tetramethyl-2,4-cyclopentadiene (7), 2,5- diphenyl-2,4-cyclopentadiene (8), or 2,3,4,5-tetraphenyl-2,4-cyclopentadiene (9) with formation of the corresponding bis[dicarbonyl(cyclopentadienyl) ruthenium(I)] complexes [RuCp# (CO)2]2 1a to 9a. The 1H and 13C NMR spectra of the new compounds 3a and 5a to 9a as well as the single crystal X-ray structures of 1a, 4a, 5a, 7a, 8a, and 9a are reported and discussed

scholarly journals Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

2018 ◽  
Vol 14 ◽  
pp. 3011-3017
Author(s):  
Akın Sağırlı ◽  
Yaşar Dürüst
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Synthetic Route ◽  
X Ray ◽  
H Nmr ◽  
2D Nmr Spectra ◽  
Tof Ms ◽  
C Nmr

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.

scholarly journals 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 ◽  
2019 ◽  
Vol 9 (36) ◽  
pp. 20505-20512 ◽  
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.

scholarly journals New Synthetic Routes for 1-Benzyl-1,4,7,10-tetraazacyclododecane and 1,4,7,10-Tetraazacyclododecane-1-acetic Acid Ethyl Ester, Important Starting Materials for Metal-coded DOTA-Based Affinity Tags

2007 ◽  
Vol 62 (3) ◽  
pp. 397-406 ◽  
Author(s):  
Stephan W. Kohl ◽  
Katharina Kuse ◽  
Markus Hummert ◽  
Herbert Schumann ◽  
Clemens Mügge ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ethyl Ester ◽  
Nmr Spectra ◽  
Acid Ethyl Ester ◽  
Affinity Tags ◽  
X Ray ◽  
H Nmr ◽  
Synthetic Routes ◽  
New Compounds ◽  
C Nmr

Two improved routes to synthesize 1-benzyl-1,4,7,10-tetraazacyclododecane (6) and 1,4,7,10- tetraazacyclododecane-1-acetic acid ethyl ester (11) are described as well as the synthesis of 1-{2-[4-(maleimido-N-propylacetamidobutyl)amino]-2-oxoethyl}-1,4,7,10-tetraazacyclododecane- 4,7,10-triacetic acid (17) and its Y, Ho, Tm, and Lu complexes. The 1H and 13C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of the intermediates 4-benzyl-1,7-bis(p-toluenesulfonyl)diethylenetriamine (3) and 1,4,7-tris(p-toluenesulfonyl)diethylenetriamine (7) are reported and discussed. The rare earth complexes of 17 have been characterized by 1H NMR spectroscopy and MALDI-TOF mass spectrometry.

Microbial Transformation of Glycyrrhetinic Acid by Colletotrichum lini AS3.4486

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.

On the chemistry and high field nuclear magnetic resonance spectroscopy of rapamycin

1980 ◽  
Vol 58 (6) ◽  
pp. 579-590 ◽  
Author(s):  
John A. Findlay ◽  
Lajos Radics
Keyword(s):  
High Field ◽  
Nmr Spectra ◽  
Resonance Spectroscopy ◽  
X Ray ◽  
Conformational Isomers ◽  
H Nmr ◽  
Neutral Compounds ◽  
Complete Assignment ◽  
Hydrolysis Of ◽  
C Nmr

Base catalysed hydrolysis of rapamycin (C51H79NO13) affords six neutral compounds identified by chemical and spectroscopic means as 2a, 3b, 3d, 5, 2,4-dimethylphenol, and L(−)-piperidine-2-carboxylic acid 6, and whose generation has been plausibly rationalized. These findings as well as detailed analyses of 13C nmr and 1H nmr spectra provide independent corroboration of the X-ray derived rapamycin crystal structure 1. Structurally homogeneous in the solid state, rapamycin is found to occur in solutions as a mixture of two conformational isomers (approximately 4:1). Through nearly complete assignment of the high field 1H (400 MHz) and 13C (100.6 MHz) nmr spectra, the isomerism is shown to be associated with trans–cis rotation of an amidic bond within the 31-membered macrolide ring. The predominant form corresponds to the conformer portrayed by X-ray analysis.

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

2003 ◽  
Vol 58 (5) ◽  
pp. 389-394 ◽  
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.

Triferrocenylborane – Molecular Structure in Solution and in the Solid State

1995 ◽  
Vol 50 (2) ◽  
pp. 201-204 ◽  
Author(s):  
Bernd Wrackmeyer ◽  
Udo Dörfler ◽  
Wolfgang Milius ◽  
Max Herberhold
Keyword(s):  
Molecular Structure ◽  
Solid State ◽  
Low Temperature ◽  
Single Crystal ◽  
Nmr Spectra ◽  
The Other ◽  
X Ray ◽  
Single Diastereomer ◽  
Structure In Solution ◽  
C Nmr

According to a single crystal X-ray structure determination all three ferrocenyl substituents of triferrocenylborane (1) adopt the same orientation with respect to the BC3-plane [P21/c monoclinic; Z = 4; a = 1353.5(3), b = 1695.6(3), c = 1056.4(2) pm, β = 109.27(3)°]. The simulated X-ray powder pattern of the single crystal is identical with the powder diagram of a macroscopic sample, indicating the presence of a single diastereomer (1a) in the solid state. However, at low temperature (< - 95 °C) in solution, the 13C NMR spectra suggest the presence of the second diastereomer (1b) in which one ferrocenyl group is oriented opposite to the other two with respect to the central BC3-plane.

Kristallstruktur und spektroskopische Untersuchung von Mg(GeMe3)2 · 2 DME / Crystal Structure and Spectroscopic Study of Mg(GeMe3)2 · 2 DME

1984 ◽  
Vol 39 (7) ◽  
pp. 855-860 ◽  
Author(s):  
Lutz Rösch ◽  
Carl Krüger ◽  
A .-P. Chiang
Keyword(s):  
Crystal Structure ◽  
Spectroscopic Study ◽  
Nmr Spectra ◽  
X Ray ◽  
H Nmr ◽  
Magnesium Compound ◽  
C Nmr

Mg(GeMe3)2 · 2 DME is synthesized by reaction of Hg(GeMe3)2 with magnesium in 1 ,2 -- dimethoxyethane. The X-ray structure, IR, Raman, 1H NMR , and 13C NMR spectra of this first organogermyl magnesium compound are reported.

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