Nitriles Organic cyanides

Organic cyanide compounds, or nitriles, have been implicated in numerous human fatalities and signs of poisoning — especially acetonitrile, acrylonitrile, acetone cyanohydrin, malonitrile, and succinonitrile. Nitriles hydrolyze to carboxylic acid and ammonia in either basic or acidic solutions. Mice (Mus sp.) given lethal doses of various nitriles had elevated cyanide concentrations in liver and brain the major acute toxicity of nitriles is CN release by liver processes (Willhite and Smith 1981). In general, alkylnitriles release CN much less readily than aryl alkylnitriles, and this may account for their comparatively low toxicity (Davis 1981). 

Organic crop production, 18 551 Organic cyanides. See Nitriles Organic dissolved matter (ODM), reverse osmosis removal of, 25 890 Organic dye lasers, optically pumped, 23 144... 

SAFETY PROFILE Nitriles are organic cyanides acrydonitrile, propionitrile, and some others resemble cyanides in toxicity. Other nitriles, such as cyanamides and cyanates, have no cyanide effect. Can react violendy with (LiAlH4 -I- H2O). The nitriles may be used as insecticides. Many are flammable. When heated to decomposition they emit highly toxic fumes of CN . See also specific compounds and CYANIDE. 

Benzyl cyanide is not outrageously poisonous like sodium cyanide. It is an organic cyanide, called a nitrile. As long as the chemist doesn t drink the stuff, he s OK. It is a somewhat smelly liquid, clear in color. 

Cyanides are based on the species CN and are invariably extremely toxic. They include silver cyanide. In contact with acids they evolve the toxic gas hydrogen cyanide. Organic cyanides are called nitriles. 

Nitriles syn. organic cyanides are organic compounds with the -CN group containing a triple bond between the carbon and nitrogen. They are toxic and... 

Nitriles are cyanide-substituted carbo lic acids, which occur naturally and synthetically, and are of the general siructure, R-CN. The naturally occurring nitriles are found in higher plants [94-97], bone oils, insects [98], and microorganisms [99,100] the synthetic ones are used industrially in benzonitrile herbicides [101], as organic solvents and in the synthesis of polymers, plastics [102,103], synthetic fibers, resins, and dye stuffs. 

Nitril nl-tr9l, trll [ISV nitr- -f -il, -He (fr. L -His -ile] (1848) n. An organic cyanide containing the group CN which on hydrolysis yields an acid with elimination of ammonia. 

Organic cyanides (nitriles) also react with mildly alkaline hydrogen peroxide, producing relatively non-toxic amides (see section 9.3.3.3). This reaction is useful in treating effluent from nitrile manufacture. 

Organic cyanides are commonly named after the corresponding acid, by changing the -ic or -ok suffix to -onitrile (hence, butyronitrile in eq. 10.16). In the lUPAC system, the suffix -nitrile is added to the name of the hydrocarbon with the same number of carbon atoms (hence butanenitrile in eq. 10.16). 

Stuhl (Entry 4), like Funabiki, used a cobalt-based catalyst system to effect the transformation of several basic alkenyl halides into nitriles [25], However, this method employed an organic cyanide source, (Et3MeN)CN, in acetonitrile. Yields were moderate, stereoselectivity was poor, and an attempt to transform an etherbearing alkenyl halide failed. 

It should also be understood that the organic cyanides and nitriles are toxic and are easily absorbed through the skin. 

Nitrilases (EC 3.5.5.1) catalyze the direct hydrolysis of organic cyanides or nitriles into the corresponding carboxylic adds without the release of intermediate amides. These enzymes are generally believed to contain a conserved Glu-Lys-Cys catalytic motif [20]. Although yet unproven due to a lack of crystal structures, the... 

Nickel catalyzed O-H additions to imsaturated systems are limited to the hydration reactions of nitriles for the synthesis of amides. These reactions have been widely studied by Prof. J. J. Garcia and his research group and their results recently reviewed [60]. They reported the isolation and characterization of Ni(0) complexes of type [(dippe)Ni(ri -NCR], R = aryl, heteroaryl or alkyl, derived from the reductive interaction of [(dippe)NiH]2 with organic cyanides. The catalytic and synthetic utility of these complexes was demonstrated first in the catalytic hydration of benzonitrile and acetonitrile [61] and then extended to dicyanobenzenes [62], to mono- and dicyanoalkanes [63] and finally to cyanopyridines [64]. 

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