Nitration anthracene

The nitration of anthracene is more difficult to perform and is not recommended as a test. 

It is probable that the nitration of anthracene with nitric acid in 7-5 % aqueous sulpholan proceeds through the rapid formation of a complex. ... 

Some information is available about the nitration of polycyclic hydrocarbons and their derivatives, but it is of no quantitative significance. The formation of a cr-complex from anthracene and nitronium ions has been mentioned ( 6.2.3, 6-3)-... 

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

Both phenanthrene and anthracene have a tendency to undergo addition reactions under the eonditions involved in eertain eleetrophilic substitutions. For example, in the nitration of anthracene in the presence of hydrochloric acid, an intermediate addition product can be isolated. This is a result of the relatively close balance in resonance stabilization to be regained by elimination (giving an anthracene ring) or addition (resulting in two benzenoid rings). 

Nitroanthrone has been prepared by the nitration of anthracene in isobutyl alcohol,1 and by the nitration of anthrone.2... 

A small isotope effect has been observed in nitration of benzene by nitronium borofluoride in tetramethylene sulphone at 30 °C (kH/kD = 0.86) and this has been attributed to a secondary effect of the change in hybridisation from sp2 to sp3 of the ring carbon during the course of the reaction109. However, naphthalene gives an isotope effect of 1.15 under the same conditions, and anthracene a value of 2.6115. It does not seem at all clear why these relatively unhindered and normally more reactive molecules should give rise to an isotope effect when benzene does not. 

Since the latter conditions pertain to aromatic nitration solely via the homolytic annihilation of the cation radical in Scheme 16, it follows from the isomeric distributions in (81) that the electrophilic nitrations of the less reactive aromatic donors (toluene, mesitylene, anisole, etc.) also proceed via Scheme 19. If so, why do the electrophilic and charge-transfer pathways diverge when the less reactive aromatic donors are treated with other /V-nitropyridinium reagents, particularly those derived from the electron-rich MeOPy and MePy The conundrum is cleanly resolved in Fig. 17, which shows the rate of homolytic annihilation of aromatic cation radicals by NO, (k2) to be singularly insensitive to cation-radical stability, as evaluated by x. By contrast, the rate of nucleophilic annihilation of ArH+- by pyridine (k2) shows a distinctive downward trend decreasing monotonically from toluene cation radical to anthracene cation radical. Indeed, the... 

Benzol hjthiophene, see Naphthalene 1,2,3-Benzotriazin-4 (3/J -one, see Azinnhos-methyl Benzotriazole, see Tetrachloroethylene Benzyl alcohol, see Benzo[a]anthracene, Benzyl butyl phthalate. Benzyl chloride, Permethrin. o-Xylene, m-Xylene, p-Xylene. Toluene 0-Benzyl alcohol, see o-Xylene m-Benzyl alcohol, see m-Xylene p-Benzyl alcohol, see p-Xylene 10-Benzyl-10-hydroanthracen-9-one, see Benzo [ a] anthracene Benzyl hydroperoxide, see Toluene Benzyl nitrate, see Toluene Benzylsuccinic acid, see Toluene... 

Peroxyacyl nitrates, see Acetaldehyde, Butane, 2-Bntanone, 2,3-Dimethylbntane Peroxybenzoic acid, see Toluene Peroxynitric acid, see Formaldehyde Peroxypropionyl nitrate, see 2-Methylpentane, Pentane Phenanthrene, see Anthracene, Bis(2-ethylhexyl) phthalate, Naphthalene Phenanthrene-9,10-dione, see Phenanthrene 9,10-Phenanthrenequinone, see Phenanthrene 4-Phenanthroic acid, see Pyrene... 

Anthracene Antimony Antimony trisulfide Barium carbonate Barium chlorate Barium nitrate Barium oxalate Boric acid Calcium carbonate Calcium oxalate Carbon black Charcoal Clay Copper... 

Hexachloroethane, Alpha naphthol, Anthracene, Aluminum powder, Smokeless powder. Naphthalene Black powder. Potassium nitrate. Coal tar, Charcoal powder, Paraffin... 

Dubois-Raymond Explosives (Fr). Proposed in 1892, mixtures which contained combustible materials such.as naphthalene, anthracene, camphor, etc together with oxidants, such. as nitrates, chromates, etc. To these was added tar, varnish, lacquer or a drying oil. 

Note Nitration of anthracene is discussed in the following papers ... 

The properties are very sensitive to composition and the charge carriers are apparently positive. Other studies have shown poly(acenaph-thalene) to be only slightly photo-conductive while the nitrated polymer exhibits a photocurrent dependent upon the degree of nitration (100). Since the number of mobile n electrons is the same as in poly (vinyl naphthalene), the authors conclude that some form of stereoregularity is required for enhanced conductivity. Complexes of poly(vinyl anthracene) with halogen molecules show enhanced conductivity and reduced activation energy which is thought to be typical of an electronic semiconductor (101). 

Anthracene is even more reactive than phenanthrene and has a greater tendency to add at the 9,10 positions than to substitute. However, the addition products of nitration and halogenation readily undergo elimination to form the 9-substitution products ... 

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