Cyclopropyl cyanide is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

consisting of a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

group as a

substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

on a

cyclopropane Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane ...

ring. It is the smallest cyclic compound containing a nitrile.

Structure

The structure of cyclopropyl cyanide has been determined by a variety of experiments, including

microwave spectroscopy Microwave spectroscopy is the spectroscopy method that employs microwaves, i.e. electromagnetic radiation at GHz frequencies, for the study of matter. History The ammonia molecule NH3 is shaped like a pyramid 0.38 Å in height, with an equilatera ...

rotational spectroscopy Rotational spectroscopy is concerned with the measurement of the energies of transitions between quantized rotational states of molecules in the gas phase. The rotational spectrum (power spectral density vs. rotational frequency) of chemical pola ...

and

photodissociation Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by absorption of light or photons. It is defined as the interaction of one or more photons wi ...

. In 1958, cyclopropyl cyanide was first studied for its rotational spectra, by Friend and Dailey. An additional experiment involving cyclopropyl cyanide was the determination of the

molecular dipole In physics, a dipole () is an electromagnetic phenomenon which occurs in two ways: * An electric dipole deals with the separation of the positive and negative electric charges found in any electromagnetic system. A simple example of this system ...

moment through spectroscopy experiments, by Carvalho in 1967.

Production

Cyclopropyl cyanide is prepared by the reaction of 4- chlorobutyronitrile with a

strong base In chemistry, there are three definitions in common use of the word "base": '' Arrhenius bases'', '' Brønsted bases'', and '' Lewis bases''. All definitions agree that bases are substances that react with acids, as originally proposed by G. ...

, such as

sodium amide Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is whit ...

in liquid

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

Reactions

Hydrolysis gives

cyclopropane carboxylic acid Cyclopropane carboxylic acid is the organic compound with the formula . It is the carboxylic acid derivative of cyclopropane. It can be prepared by hydrolysis of cyanocyclopropane, which is obtained by base-induced cyclization of 4-chlorobutyroni ...

]. Cyclopropyl cyanide, when heated to 660-760K and under pressure of 2-89torr, becomes cis and trans crotonitrile and

allyl cyanide Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is colorless and soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent ...

molecules, with some presence of

methacrylonitrile Methacrylonitrile (or 2-Methylprop-2-enenitrile), MeAN in short, is a chemical compound that is an unsaturated aliphatic nitrile, widely used in the preparation of homopolymers, copolymers, elastomers, and plastics and as a chemical intermediate i ...

. This is an isomerization reaction that is homogeneous with rate of first order. The reaction result is due to the biradical mechanism, which involves the formation of carbon radicals as the three carbon ring opens up. The radicals then react to yield carbon=carbon double bonds. Cyclopropancarbonitril Isomerisierung

References

{{reflist Spectroscopy Cyclopropyl compounds Nitriles