Isobutyronitrile

Last updated
Isobutyronitrile
Isobutyronitrile.svg
Names
Preferred IUPAC name
2-Methylpropanenitrile
Other names
Isopropyl cyanide; 2-Methylpropionitrile
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.043 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-147-5
KEGG
PubChem CID
RTECS number
  • TZ4900000
UNII
UN number 2284
  • InChI=1S/C4H7N/c1-4(2)3-5/h4H,1-2H3
    Key: LRDFRRGEGBBSRN-UHFFFAOYSA-N
  • InChI=1/C4H7N/c1-4(2)3-5/h4H,1-2H3
    Key: LRDFRRGEGBBSRN-UHFFFAOYAP
  • CC(C)C#N
Properties
C4H7N
Molar mass 69.107 g·mol−1
AppearanceColorless liquid [1]
Odor Almond-like [1]
Melting point −72 °C (−98 °F; 201 K)
Boiling point 103.9 °C (219.0 °F; 377.0 K) [2]
Very soluble in organics
1.372
4.29 D
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H224, H225, H300, H301, H310, H311, H315, H319, H331, H335, H370, H371, H372
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P309+P311, P310, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 47 °C (117 °F; 320 K) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isobutyronitrile is a complex organic molecule that has recently been found in several meteorites arrived from space. The singularity of this chemical is due to the fact that it is the only one among the molecules arriving from the universe that has a branched, rather than straight, carbon backbone. The backbone is also larger than usual, in comparison with others.

Contents

History

Both isobutyronitrile and its straight-chain isomer, Butyronitrile, were detected by astronomers from Cornell University, the Max Planck Institute for Radio Astronomy and the University of Cologne by means of using the Atacama Large Millimeter/submillimeter Array (ALMA) [3] — a set of radiotelescopes in Chile. The chemical was found within an immense gas cloud in the star-forming region called Sagittarius B2. This interstellar space is located at about 300 light years away from the Galactic Center Sgr A*. [4] and about 27,000 light years from Earth. [5]

About 50 individual features for isobutyronitrile and 120 for normal propyl cyanide (n-propyl cyanide) were identified in the ALMA spectrum of the Sagittarius B2 region. The published astrochemical model indicates that both isomers are produced within or upon dust grain ice mantles through the addition of molecular radicals, albeit via differing reaction pathways.

Scientists have come to the conclusion that isobutyronitrile could have been essential for the creation of primary life. The discovery of this particular cyanide suggests that the complex molecules needed for life may have their origins in interstellar space. Those molecules would have been rising during the process of early star formation and been transferred to our planet later. [6]

According to Rob Garrod, this detection opens a new frontier in the field regarding the complexity of molecules that can be formed in interstellar space and that might ultimately find their way to the surfaces of planets. How widespread these complex organic molecules really are in our Galaxy is one of the questions raised by this new discovery.

Composition and structure

Isobutyronitrile (C3H7CN) contains a carbon atom bounded by a simple link to two methyl (-CH3) structures and to a cyano group (–CN). The cyano group is constituted by a triple link bond between one carbon and one nitrogen atom. The greatest contribution to the production of i-PrCN comes from the reaction of CN radicals (which are accreted from the gas) with the CH3CHCH3 radical, whereas the dominant formation mechanism for n-PrCN is the addition of C2H5 and CH2CN, a process that has no equivalent for the production of i-PrCN. i-PrCN production dominates all reaction mechanisms for which parallel processes are available to both isomers.It is also the most complex shaped molecule in the history. [7]

Rotational spectrum

The rotational spectrum of the branched isomer iso- or i-PrCN, which had only been previously studied to a limited extent in the microwave region, has recently been extensively recorded in the laboratory from the microwave to the submillimeter wave region along with a redetermination of the dipole moment, which appears to be 4.29 D. The latter uncertainty assumes the same source size and rotation temperature for both isomers.

Scientists were able to observe transitions in both types of cyanides. Thus, the microwave spectrum of the isobutyronitrile has been recorded from 26.5 to 40.0 GHz. Three different excited states were found in the R-branch of i-PrCN. In the experiments carried out by the scientists, different parameters were studied: The bond distance between the different atoms and the angles between them. The results indicated that the bond distance between de carbon atom and the cyano group is 1.501 Å; the angle between the three carbon atoms is 113º while the angle between the CCC and the CN bond is 53.8º. Two different torsional modes were observed, according to the relative intensities of the excited state lines, the frequencies of which were, respectively, 200±20 and 249±10 cm−1. This could give an idea of the internal rotation energy of this molecule, which has been found to be of 3.3 Kcal/mole. [8]

Importance in life's origin

The branched carbon structure of isobutyronitrile is a common feature in those molecules that are considered to be necessary for life – such as amino acids, which are the building blocks of proteins. This new discovery lends weight to the idea that biologically crucial molecules, like the mentioned amino acids which are also commonly found in meteorites, were produced even before the process of star formation or before planets such as the Earth were formed.

The importance of the cyanides found in comets remains in their C-N bond. This bond has been proved to participate in the abiotic amino acid synthesis.

The two cyanide molecules – isobutyronitrile and n-butyronitrile – are the largest molecules yet detected in any star-forming region.

Properties

Some more specific properties are:

Hazards

Applications

3D space-filling model of the isobutyronitrile molecule. Isopropylcyanide.gif
3D space-filling model of the isobutyronitrile molecule.

Chemically speaking, the simple inorganic cyanides behave as chlorides in many ways. Organic nitriles act as solvents and are reacted further for various applications such as: [10] Working as an extraction solvent for fatty acids, oils and unsaturated hydrocarbons. They are also good solvents for spinning and casting and extractive distillation based on its selective miscibility with organic compounds and can act as removing agents of colouring matters and aromatic alcohols. Inorganic cyanides are also able to perform a recrystallization of steroids or to be compounds for organic synthesis. Therefore, they basically act as solvents or chemical intermediates in biochemistry (pesticide sequencing and DNA synthesis, for example).

Some other useful applications of these organic nitriles are the performance of high-pressure liquid chromatographic analysis. Also, the action they have as catalysts and components of transition-metal complex catalysts, stabilizers for chlorinated solvents. Furthermore, they may work as chemical intermediates and solvents for perfumes and pharmaceutical products.

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Cyanide</span> Any molecule with a cyano group (–C≡N)

In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

<span class="mw-page-title-main">Hypothetical types of biochemistry</span> Possible alternative biochemicals used by life forms

Hypothetical types of biochemistry are forms of biochemistry agreed to be scientifically viable but not proven to exist at this time. The kinds of living organisms currently known on Earth all use carbon compounds for basic structural and metabolic functions, water as a solvent, and DNA or RNA to define and control their form. If life exists on other planets or moons it may be chemically similar, though it is also possible that there are organisms with quite different chemistries – for instance, involving other classes of carbon compounds, compounds of another element, or another solvent in place of water.

<span class="mw-page-title-main">Functional group</span> Set of atoms in a molecule which augment its chemical and/or physical properties

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

<span class="mw-page-title-main">Organic compound</span> Chemical compound with carbon-hydrogen bonds

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Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structural formula H−C≡N. It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature.

<span class="mw-page-title-main">Astrochemistry</span> Study of molecules in the Universe and their reactions

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<span class="mw-page-title-main">Cyanohydrin</span> Functional group in organic chemistry

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<span class="mw-page-title-main">Butyronitrile</span> Chemical compound

Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.

<span class="mw-page-title-main">Isocyanic acid</span> Chemical compound (H–N=C=O)

Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as H−N=C=O. It is a colourless, volatile and poisonous substance, with a boiling point of 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid (aka. cyanol).

<span class="mw-page-title-main">Dicyanoacetylene</span> Organic compound (N≡C−C≡C−C≡N)

Dicyanoacetylene, also called carbon subnitride or but-2-ynedinitrile (IUPAC), is a compound of carbon and nitrogen with chemical formula C4N2. It has a linear molecular structure, N≡C−C≡C−C≡N, with alternating triple and single covalent bonds. It can be viewed as acetylene with the two hydrogen atoms replaced by cyanide groups.

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References

  1. 1 2 "CDC - NIOSH Pocket Guide to Chemical Hazards - Isobutyronitrile". Cdc.gov. Retrieved 2015-10-08.
  2. 1 2 CID 6559 from PubChem
  3. "Complex Organic Molecules Discovered in Infant Star System".
  4. "New molecule found in space connotes life origins". astronomy.com. September 29, 2014.
  5. "New molecule found in space connotes life origins | Cornell Chronicle". www.news.cornell.edu. Retrieved 2015-10-27.
  6. "Science for Scientists".
  7. "Interstellar molecules are branching out".
  8. Durig, J.R.; Li, Y.S. (1974). "Microwave spectrum, dipole moment and structure of isopropyl cyanide". Journal of Molecular Structure. 21 (2): 289–297. Bibcode:1974JMoSt..21..289D. doi:10.1016/0022-2860(74)80052-9.
  9. "Big Chemical Encyclopedia".[ permanent dead link ]
  10. "Isobutyronitrile (Isopropyl Cyanide)".

Bibliography

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  2. Öberg KI, Guzmán VV; et al. (2015-10-27). "The comet-like composition of a protoplanetary disk as revealed by complex cyanides". Nature. 520 (7546): 198–201. arXiv: 1505.06347 . Bibcode:2015Natur.520..198O. doi:10.1038/nature14276. PMID   25855455. S2CID   205242974.