Cyanobenzene

Chemical Designations - Synonyms Benzoic Acid Nitrile, Cyanobenzene, Phenylcyanide Chemical Formula C HjCN. 

Cyan-Mthert m. cyanic ester. -Mthyl, n. ethyl cyanide, -bad, n. cyanide bath. -baryum,n. barium cyanide, -benzol, n. cyanobenzene. -bromid, n. cyanogen bromide, -calcium, n. calcium cyanide, -chlorid, n. cyanogen chloride. -doppelsalZt n. double cyanide. 

Draw resonance structures of cyanobenzene (C H5CN) that show how it functions as a meta-directing substituent. 

Cupron, b50 Cyanoacetonitrile, m5 Cyanoanilines, al21, al22, al23 Cyanobenzene, b51 2-Cyanoethanol, hl73 Cyanoethylene, a63 Cyanomethane, a29... 

Aiyl fluorides and iodides cannot be prepared by direct halogenatlon. The cyano group cannot be Introduced by nucleophilic substitution of of Aromatic chlorine in chlorobenzene but cyanobenzene can be easily obtained from diazonium salt. 

Reductive elimination on transition metal complexes seems to be enhanced by coordination of electron-withdrawing 71-acids such as cyanobenzene and cyanoethylene. For example, the reductive elimination reaction of NiR2(bpy) (R=alkyl or aryl group bpy =2,2 -bipyridyl) is enhanced by electron-withdrawing olefinic and aromatic compounds [12-16] (Scheme 1). 

The study of cyanobenzene ion treated an ion whose thermochemistry was already well studied by PEPICO. However, the TRPD result was at a substantially lower internal energy, so that the measured dissociation rate of 5 x 10 s at 4.10 eV internal energy was slower by more than an order of magnitude than the slowest dissociations probed by PEPICO. By extension of the known rate-energy curve nearer to threshold, this added quantitative confidence to the RRKM extrapolation and considerably strengthened the g value for Equation (5) of 3.02 eV assigned... 

Cyanide of Calcium Cyanoacetic Acid Cyanobenzene 2-Cyanoethanol Cyanoethylene... 

Fig. 8.15 The relation between i cr of the spectra of charge-transfer complexes and the half-wave potentials of electron acceptors [53]. Electron acceptor derivatives of phthalic anhydride, quinone and nitrobenzene, and tetra-cyanobenzene and tetracyanoethylene.

The oxidation-reduction potentials of metal ions differ in different solvents due chiefly to differences in the strength of coordination of the solvents to the metal ions. Thus, Schaap and coworkers,33 who measured reduction potentials polarographically in anhydrous ethylenediamine, found the order of half-wave potentials to be Cd2+ > Pb2+ > Cu2+ - Cu+ > Ti+, whereas, in aqueous solution, the order is Cd2+ > Ti+ > Pb2+ > Cu2+ -> Cu+. Oxidation—reduction potentials have been measured in a great variety of non-aqueous solvents, both protonic and non-protonic. Among the former are liquid ammonia and concentrated sulfuric acid.34 Among the latter are acetonitrile, cyanopropane, cyanobenzene, dimethyl sulfoxide, methylene chloride, acetone, tet-rahydrofuran, dimethylformamide and pyridine.34... 

Cyanobenzene, AJ09 U-Cyanobenzenediazonium tetra-fluoroborate, A155... 

Reaction of 4-t-butoxycarbonylbenzene oxide (111, R = t-Bu) with lithium hydroxide in aqueous dioxane yielded (-butyl (rans-2,3-dihydroxy-2,3-dihydrobenzoate (255).152 In an aqueous solution, the compound undergoes both H30+- and water-catalyzed aromatization as well as a HO -catalyzed reaction at higher pH ranges. With a more electron-deficient 4-cyanobenzene oxide (256) the kinetics of the base-catalyzed hydrolysis show a first-order dependence on [HO ] above pH 9.2... 

The potassium salt of the phthalodinitrile (ort/zo-dicyanobenzene) anion radical also reacts with an electrophile according to the electron transfer scheme. If the electrophile is tert-butyl halide, the reaction proceeds via the mechanism, including at the first-stage dissociative electron transfer from the anion radical to alkyl halide, followed by recombination of the generated tertiary butyl radical with another molecule of the phthalodinitrile anion radical. The product mixture resulting in the reaction includes 4-tert-butyl-1,2-di-cyanobenzene, 2-tert-bytylbenzonitrile, and 2,5-di(tert-butyl)benzonitrile (Panteleeva and co-authors 1998). 

Yasuda, Pac, and Shima reported the photoamination of aromatic compounds by use of ammonia and primary amines as nucleophiles in the presence of m-di-cyanobenzene as an electron acceptor [30,32], Irradiation of an acetonitrile-water (9 1) solution containing phenanthrene and m-dicyanobenzene in the presence of ammonia or primary amines gives 9-amino-9,10-dihydrophenanthrene deriva-... 

Photo-NOCAS reactions of p-dicyanobenzene with 2-methylpropene in acetonitrile afforded novel 3,4-dihydroisoquinoline derivatives, as shown in Scheme 132 [482], This photoreaction is initiated by a single electron transfer from olefin to p-dicyanobenzene. Acetonitrile as a nucleophile combined with the alkene radical cation and the resulting radical cation adds to the radical anion of 1,4-di-cyanobenzene. Cyclization to the ortho position of phenyl group followed by loss... 

Nitriles Unlikely to be detected except in case of acetonitrile (CH,CN) and propionitrile (C2H5CN) M + 1 ion may appear (especially at higher pressures) M - 1 peak is weak but detectable (R-CH=C=N ) base peak at m/e = 41 (CH2=C=NH) McLafferty rearrangement possible loss of HCN is case of cyanobenzenes... 

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