Cyananthracene, II. Mitteilung

Waldmann, H.; Stengl, Rudolf

doi:10.1002/cber.19500830210

Cited by 7 publications

(1 citation statement)

References 3 publications

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“…1,8‐diiodoanthracene (1 g, 2.3 mmol) was reacted with CuCN (0.5 g, 5.58 mmol) as described above to yield 0,45 g (60%) of yellow crystals; mp > 300 °C (Lit 300,5 °C); 1 H NMR (300 MHz; CDCl 3 ), δ 9.16 (s, 1H), δ 8.64 (s, 1H), δ 8.30 (dd, 2H, J = 8.7 and J = 1.2 Hz), δ 8.07 (dd, 2H, J = 6.9 and J = 1.2 Hz), δ 7.62 (dd, 2H, J = 8.7 and J = 6.9 Hz); UV–VIS (DMF) 406 nm (log ε = 3.72), 385 nm (log ε = 3.84), 364 nm (log ε = 3.78); EPR (radical anion, DMF) a 2N = 0.28 G, a H = 5.33 G, a 2H = 4.08 G, a 2H = 3.34 G, a H = 3.23 G, a 2H = 0.28 G.…”

Section: Methodsmentioning

confidence: 99%

Dicyanoaromatic radical anions as mixed valence species

Moneo

Carvalho

Telo

2012

J of Physical Organic Chem

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The reduction of nine symmetric dicyanoaromatic radical anions by sodium amalgam in the presence of cryptand[2.2.2] was studied using cyclic voltammetry and using optical and electron paramagnetic resonance (EPR) spectroscopies in two aprotic solvents. All radicals are charge‐delocalized (Class III) mixed valence species, as shown by the weak solvatochromism of their low‐energy optical bands and by the vibrational structure exhibited by most of the bands. The maximum of the low‐energy optical transition decreases logarithmically with the number of bonds (n) between cyano groups in a series of p‐phenylene‐bridged radicals, from p‐phenyl (n = 5) to p‐quaterphenyl (n = 17), although the energy of the latter lies higher than the value predicted by the linear regression. The energy of this band decreases linearly with the cos2 value of the torsion angle between phenyl rings in the spectra of biphenyl‐4,4′‐dicarbonitrile radical anion and their methyl‐substituted derivatives. The fact that charge delocalization is maintained in radicals with non‐Kekulé bridges, with unusually large bridges and with bridges with highly twisted biphenyl systems suggests that cyano charge‐bearing units have small reorganization energies and induce high electronic couplings through the bridges. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Methodsmentioning

confidence: 99%

Dicyanoaromatic radical anions as mixed valence species

Moneo

Carvalho

Telo

2012

J of Physical Organic Chem

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Platelet Aggregation Inhibiting and Anticoagulant Effects of Oligoamines, XW: Oligoamines with Fluorescent Properties Part A: Fluorescent Bridged Nitrogen Functions

Rehse

Seidel

1992

Archiv der Pharmazie

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Acetylation of anthracene by the Friedel‐crafts reaction using ethylene chloride as the solvent

Bassilios

Shawky

Salem

1963

Recl. Trav. Chim. Pays‐Bas

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Acetylation of anthracene by the Friedel-Crafts Reaction using ethylene chloride as the solvent leads to a high yield of 1-acetylanthracene. Diacetylation gives a mixture of 1,s-and 1,s-diacetylanthtacene. Oxidation to the corresponding acetylanthraquinones and carboxylic acids is described. IntroductionThe authors i n a previous publication 1 described the acetylation of anthracene using chloroform as the solvent. This, publication deals with the reaction in another solvent, ethylene chloride, which, although resembling chloroform in many respects, showed a different orienting effect.

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Cyananthracene, II. Mitteilung

Abstract: Durch Kochen mit Phthalsäureanhydrid oder mit seinen höhersiedenden Chlor‐Derivaten wurden aus verschiedenen Anthracencarbonsäureamiden glatt die entsprechenden Nitrile gewonnen.

Cited by 7 publications

References 3 publications

Dicyanoaromatic radical anions as mixed valence species

Dicyanoaromatic radical anions as mixed valence species

Platelet Aggregation Inhibiting and Anticoagulant Effects of Oligoamines, XW: Oligoamines with Fluorescent Properties Part A: Fluorescent Bridged Nitrogen Functions

Acetylation of anthracene by the Friedel‐crafts reaction using ethylene chloride as the solvent

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