Über sterisch gehinderte freie Radikale, XIX. Stabile 4,4′,4″‐trisubstituierte Triphenylmethyl‐Radikale

Dünnebacke, Dieter; Neumann, Wilhelm P.; Peñéñory, Alicia B.; Stewen, U.

doi:10.1002/cber.19891220322

Cited by 26 publications

(31 citation statements)

References 28 publications

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“…, hyperfine interactions to other nuclei are resolved. As shown in Figure , the experimental spectrum is well reproduced by assuming hyperfine couplings to four identical hydrogen atoms each (the ortho and meta protons of the anisyl rings) of 1.1 G and 0.7 G, and to two sets of two hydrogen atoms (the α and β hydrogens at the ferrocenyl substituent) of 2.1 G and 1.4 G. The reduced magnitudes of hyperfine splittings to the anisyl rings compared with the corresponding tris(anisyl) methyl and related radicals also indicate that the ferrocenyl substituent bears a comparably larger spin density.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Oßwald

Casper

Anders

et al. 2018

Chemistry A European J

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Four monoferrocenyl tritylium derivatives with donor-substituted (OMe, NMe ) aryl rings are reported, along with their spectroscopic and electrochemical properties. All the complexes show a one-electron reduction and a quasi-reversible ferrocene oxidation at a very positive potential. Small quadrupole splittings, ΔE , in Mößbauer spectra agree with highly electron-deficient ferrocenes. Comparison of the experimental half-wave potentials for ferrocene oxidation, E (Fc/Fc ), with those estimated from established correlations of E (Fc/Fc ) with ΔE indicates that the E values of the anisyl-substituted congeners FcOMe and FcMeOMe are affected by Coulombic repulsion between the positive charges at the Fe ion and the neighboring methylium site. Electronic spectra are recorded and interpreted with the aid of quantum chemical calculations. UV/Vis spectroelectrochemical measurements as well as chemical reduction provide insight into the redox-induced color changes upon ferrocene oxidation or upon reduction to the neutral trityl radicals. The neutral radicals reversibly form EPR-silent dimers. This process is studied by temperature-dependent EPR spectroscopy, and thermodynamic data for their dimerization are determined. Experimental and quantum chemical data suggest that the dimers assume classical hexaarylethane structures as opposed to normal or "offset" Jacobson-Nauta-type structures.

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Section: Resultsmentioning

confidence: 99%

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Oßwald

Casper

Anders

et al. 2018

Chemistry A European J

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“…The silver atoms are in a distorted tetrahedral geometry. Unlike the triflate in the previous structures, the counterion tetrafluoroborate (11) In all three cases of the complexes (6)(7)(8), the triflate counterion bonds to silver(I). This triflate-silver coordination is well-exemplified in other 14 crystal structures of the organosilver(I) triflate complexes reported by us and others.…”

Section: Graphitic Sheet Structure Of [Ag‚3‚cf 3 So 3 ] (8)mentioning

confidence: 93%

“…After refluxing at 90-100°C for 2h in an oil bath, the reaction mixture was allowed to cool to room temperature and evaporated to dryness on a rotary evaporator and then on a vacuum line. Without further purification, the yellowish intermediate product thus obtained was dissolved in DMF (5 mL), followed by addition of NaCN powder (0.2 g, 0.4 mmol), stirred at room temperature overnight, and finally heated to 50°C for 3 h. The reaction mixture was poured into ice-water, (6) 14.6273 (14) 8.8148 (8) 18.0187 (4) 10.230 (2) 14.4951(2) b (Å) 13.6029 (10) 15.161 (2) 10.5031 (6) 14.9717 (3) 11.839 (2) 16.5954(1) c (Å) 13.8822 (12) 17.010 (2) 10.8323 (11) 23.5469 (5) 26.071 (4) 17.0387(1) R (deg) 108.743 (6) 85.481 (7) 81.782 (6) [Ag‚1‚CF3SO3]‚2C6H6 (6). A solution of silver(I) triflate (6.9 mg, 0.27 mmol) in benzene (3.5 mL) was added to a solution of 1 (9.5 mg, 0.27 mmol) in benzene (3.5 mL) in a clean flask equipped with a Teflon-lined screw-cap.…”

Section: 4′-dicyanobenzophenone (3)mentioning

confidence: 98%

Coordination Networks ofC₃_vandC₂_vPhenylacetylene Nitriles and Silver(I) Salts: Interplay of Ligand Symmetry and Molecular Dipole Moments in the Solid State

Choe

Kiang

et al. 1999

Chem. Mater.

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Five organic ligands of C 3v and C 2v symmetry, 3,5-bis(4-cyanophenylethynyl)cyanobenzene (1), 3,5-bis(4-cyanophenylethynyl)-4-methoxycyanobenzene (2), and 4,4′-dicyanobenzophenone (3), cyanotris(4-cyanophenyl)methane (4), and tris(4-cyanophenyl)methanol (5), have been prepared, crystallized with silver(I) salts, and characterized by single-crystal X-ray study. Crystallographic data are as follows: [Ag‚1‚CF 3 SO 3 ]‚2C 6 H 6 , triclinic, P1 h (no. 2), a ) 10.0864-(6) Å, b ) 13.6029(10) Å, c ) 13.8822(12) Å, R ) 108.743(6)°, ) 95.063(6)°, γ ) 95.484(5)°, °, Z ) 4. Τhe crystal structures are similar to those previously found for the T d and D 3h phenyl nitriles with Ag(I) salts and can be related to the diamond and graphite topologies. However, due to the intrinsic symmetry of C 3v and C 2v ligands, permanent molecular dipole moments are always present. The stacking sequences found in three graphite-like structures are in an antiparallel fashion so that the net dipole moments of the crystals are zero. Similarly, the diamond-like structure is composed of two interpenetrating diamondoid nets oriented in such a way that the net dipole moment of the two nets combined is zero.

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“…quality and freshly distilled before use. [26] Tris (27): Under N 2 atmosphere and ice cooling, 26 (1.87 g, 5.00 mmol) was dissolved in abs. As petroleum ether (PE) the fraction 40-80 8C was used.…”

Section: Methodsmentioning

confidence: 99%

Development of an (S)‐1‐{2‐[Tris(4‐methoxyphenyl)methoxy]ethyl}piperidine‐3‐carboxylic acid [(S)‐SNAP‐5114] Carba Analogue Inhibitor for Murine γ‐Aminobutyric Acid Transporter Type 4

Pabel

Faust²,

Prehn

et al. 2012

ChemMedChem

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A series of GABA uptake inhibitors related to (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114], the most potent mGAT4 inhibitor known so far, were synthesized and biologically evaluated for their inhibitory potency at the four GABA uptake transporters mGAT1-4 stably expressed in HEK-293 cell lines. New analogues were developed with potencies that are similar to or slightly higher than those of current mGAT4 inhibitors, but with distinctly improved chemical stability. (S)-Nipecotic acid derivatives possessing a 2-[1-(4-methoxy-2-methylphenyl)-1,1-bis(4-methoxyphenyl)methoxy]ethyl (DDPM-859) or a 4,4,4-tris(4-methoxyphenyl)but-2-en-1-yl moiety (DDPM-1457) were found to exhibit pIC(50) values of 5.78 and 5.87, respectively. Thus, as mGAT4 inhibitors, these compounds compare well with (S)-SNAP-5114 (pIC(50) =5.71), but are far more stable than the latter. Moreover, DDPM-859 displays a more favorable subtype selectivity for mGAT4 versus mGAT3 than does (S)-SNAP-5114.

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Über sterisch gehinderte freie Radikale, XIX. Stabile 4,4′,4″‐trisubstituierte Triphenylmethyl‐Radikale

Cited by 26 publications

References 28 publications

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Coordination Networks ofC₃_vandC₂_vPhenylacetylene Nitriles and Silver(I) Salts: Interplay of Ligand Symmetry and Molecular Dipole Moments in the Solid State

Development of an (S)‐1‐{2‐[Tris(4‐methoxyphenyl)methoxy]ethyl}piperidine‐3‐carboxylic acid [(S)‐SNAP‐5114] Carba Analogue Inhibitor for Murine γ‐Aminobutyric Acid Transporter Type 4

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Über sterisch gehinderte freie Radikale, XIX. Stabile 4,4′,4″‐trisubstituierte Triphenylmethyl‐Radikale

Cited by 26 publications

References 28 publications

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl‐Substituted Tritylium Dyes

Coordination Networks ofC3vandC2vPhenylacetylene Nitriles and Silver(I) Salts: Interplay of Ligand Symmetry and Molecular Dipole Moments in the Solid State

Development of an (S)‐1‐{2‐[Tris(4‐methoxyphenyl)methoxy]ethyl}piperidine‐3‐carboxylic acid [(S)‐SNAP‐5114] Carba Analogue Inhibitor for Murine γ‐Aminobutyric Acid Transporter Type 4

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Coordination Networks ofC₃_vandC₂_vPhenylacetylene Nitriles and Silver(I) Salts: Interplay of Ligand Symmetry and Molecular Dipole Moments in the Solid State