Cyclopropyl cyanide is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

consisting of a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including me ...

group as a

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...

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 ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself i ...

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 spectra of chemical polarity, polar molecules can be measured in Absorption (optics), ...

and

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

. In 1958, cyclopropyl cyanide was first studied for its rotational spectra, by Friend and Dailey. 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 i ...

moment through spectroscopy experiments, by Carvalho in 1967.

Production

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

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

, 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 compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...

Reactions

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 intermediat ...

. This is an isomerization reaction that is homogeneous with rate of first order. The reaction result is due to the biradical mechanism, involving 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