Cyclopropyl cyanide
{{Educational assignment}}
{{Chembox
| ImageFile =C3H5CN.svg
| ImageSize = 250
| ImageAlt =
| PIN = Cyclopropanecarbonitrile
| OtherNames = Cyanocyclopropane
| Section1 = {{Chembox Identifiers
| CASNo = 5500-21-0
| CASNo_Ref = {{Cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AFU99GZS5D
| ChemSpiderID = 71940
| EC_number = 226-836-8
| PubChem = 79637
| SMILES = N#CC1CC1
| StdInChI=1S/C4H5N/c5-3-4-1-2-4/h4H,1-2H2
| StdInChIKey = AUQDITHEDVOTCU-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| Formula = C4H5N
| MolarMass = 67.0892g/mol{{cite web|title=cyclopropanecarbonitrile - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=79637#x27|publisher=PubChem}}
| Appearance = clear to light yellow liquid
| Density = 0.911g/mL
| MeltingPtC = -25
| BoilingPtC =135
| Solubility = soluble in water{{cite web|title=Cyclopropyl cyanide|url=http://www.chemicalbook.com/ProductMSDSDetailCB9158593_EN.htm|publisher=Chemical Book}}
| LogP =1.196}}
| Section4 = {{Chembox Thermochemistry
| DeltaHc =182.7
| DeltaHf =
| Entropy =
| HeatCapacity = }}
| Section3 = {{Chembox Hazards
| MainHazards = Toxic, hazardous if inhaled, contacted with skin, or swallowed
| FlashPtC =40
| AutoignitionPt =
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|301|311|315|319|330|331|335}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|280|284|301+310|302+352|303+361+353|304+340|305+351+338|310|311|312|320|321|322|330|332+313|337+313|361|362|363|370+378|403+233|403+235|405|501}}
}}
}}
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.
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.{{cn|date=May 2018}} An additional experiment involving cyclopropyl cyanide was the determination of the molecular dipole moment through spectroscopy experiments, by Carvalho in 1967.{{cite journal|last=Bizzocchi|first=Luca|author2=Claudio Degli Esposti |author3=Luca Dore |author4=Zbigniew Kisiel |title=Submillimetre-wave spectrum, 14N-hyperfine structure, and dipole moment of cyclopropyl cyanide|journal=Journal of Molecular Spectroscopy|date=September–October 2008|volume=251|issue=1–2|pages=138–144|doi=10.1016/j.jms.2008.02.009|bibcode=2008JMoSp.251..138B}}
Production
Cyclopropyl cyanide is prepared by the reaction of 4-chlorobutyronitrile with a strong base, such as sodium amide in liquid ammonia.{{cite journal|last=Schlatter|first=M. J.|journal=Organic Syntheses|title=Cyclopropyl Cyanide|year=1943|volume=23|pages=20|doi=10.15227/orgsyn.023.0020}}
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, which involves the formation of carbon radicals as the three carbon ring opens up. The radicals then react to yield carbon=carbon double bonds.{{cite journal|last=Luckraft|author2=Robinson|journal=International Journal of Chemical Kinetics|year=1973|volume=5|pages=137–147|doi=10.1002/kin.550050112|title=Kinetics of the reactions of cyclopropane derivatives. III. Gas-phase unimolecular isomerization of cyclopropyl cyanide to the cyanopropenes}}
