Cyclopropyl cyanide

Cyclopropyl cyanide is an organic compound consisting of a nitrile group as a substituent on a cyclopropane ring. It is the smallest cyclic compound containing a nitrile.

Cyclopropyl cyanide
Names
IUPAC name
cyclopropanecarbonitrile
Other names
Cyclopropanecarbonitrile, Cyanocyclopropane,
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.397
Properties
C4H5N
Molar mass 67.0892g/mol[1]
Appearance clear to light yellow liquid
Density 0.911g/mL
Melting point −25 °C (−13 °F; 248 K)
Boiling point 135 °C (275 °F; 408 K)
soluble in water[2]
log P 1.196
Hazards
Main hazards Toxic, hazardous if inhaled, contacted with skin, or swallowed
Flash point 40 °C (104 °F; 313 K)
not applicable
Thermochemistry
182.7
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Structure

The structure of cyclopropyl cyanide has been determined by a variety of experiments, including microwave spectroscopy, rotational spectroscopy and photodissociation. 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 moment through spectroscopy experiments, by Carvalho in 1967.[3]

Production

Cyclopropyl cyanide is prepared by reaction of 4-chlorobutyronitrile with a strong base, such as sodium amide in liquid ammonia.[4]

Reactions

Cyclopropyl cyanide, when heated to 660-760K and under pressure of 2-89torr, becomes cis and trans crotonitrile and allyl cyanide molecules, with some presence of methacrylonitrile. 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.[5]

References
  1. "cyclopropanecarbonitrile - Compound Summary". PubChem.
  2. "Cyclopropyl cyanide". Chemical Book.
  3. Bizzocchi, Luca; Claudio Degli Esposti; Luca Dore; Zbigniew Kisiel (September–October 2008). "Submillimetre-wave spectrum, 14N-hyperfine structure, and dipole moment of cyclopropyl cyanide". Journal of Molecular Spectroscopy. 251 (1–2): 138–144. Bibcode:2008JMoSp.251..138B. doi:10.1016/j.jms.2008.02.009.
  4. Schlatter (1955). "Cyclopropyl Cyanide". Organic Syntheses. 3: 223. doi:10.1002/0471264180.os023.08. ISBN 0471264229.
  5. Luckraft; Robinson (1973). "Kinetics of the reactions of cyclopropane derivatives. III. Gas-phase unimolecular isomerization of cyclopropyl cyanide to the cyanopropenes". International Journal of Chemical Kinetics. 5: 137–147. doi:10.1002/kin.550050112.
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