What is Cyanogen?

Information about Cyanogen



Cyanogen
IUPAC nameEthanedinitrile
Other namesCyanogen
Carbon nitride
Dicyan
Dicyanogen
Nitriloacetonitrile
Oxalic acid dinitrile
Oxalonitrile
Oxalyl cyanide
Identifiers
CAS number460-19-5
SMILESN#CC#N
style="background: #F8EABA; text-align: center;" colspan="2" Hazards
NFPA 704
4
4
2
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


Cyanogen is the chemical compound with the formula (CN)2. It is a colorless, toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups (analogous to diatomic halogen molecules, such as Cl2 but it far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C−C≡N, although other isomers have been detected. Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example Cyanogen bromide is the compound with the structure NCBr.[1]

Cyanogen is the anhydride of oxamide:
H2NC(O)C(O)NH2 → NCCN + 2 H2O

Preparation

Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide:
2 Hg(CN)2 → (CN)2 + 2 HgCN
Alternatively, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.[2]
2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4


Industrially, it is made by the oxidation of hydrogen cyanide, usually using chlorine over an activated silicon dioxide catalyst or nitrogen dioxide over a copper salt. It is also formed when nitrogen (N2) and acetylene (C2H2) are made to react by an electrical spark or discharge.[3]

History

Cyanogen has a long history and was probably first generated by Carl Scheele around 1782 in the course of his studies of hydrogen cyanide.[4] [5]The first confirmed synthesis was reported 1802, when it was used to make what we now know as cyanogen chloride. It attained importance with the growth of the fertilizer industry in the late nineteenth century and is still an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of nitrocellulose.

Safety

Like other inorganic cyanides, cyanogen is very toxic, as it undergoes reduction to cyanide, which binds more strongly than oxygen to the cytochrome c oxidase complex, thus interrupting the mitochondrial electron transfer chain.Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions and death, depending on exposure.[6]

Cyanogen produces the hottest known natural flame with a temperature of over 4525°C (8180°F) when it burns in oxygen.[7]

See also

References

1. ^ Hartman W. W.; Dreger, E. E. "Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).[1]
2. ^ T. K. Brotherton, J. W. Lynn (1959). "The Synthesis And Chemistry Of Cyanogen". Chemical Reviews 59 (5): 841 - 883. DOI:10.1021/cr50029a003. 
3. ^ A. A. Breneman (1959). "Showing the Progress and Development of Processes for the the manufacture of Cyanogen and its Derivates (in: THE FIXATION OF ATMOSPHERIC NITROGEN". Journal of the American Chemical Society 11 (1): 2-28. DOI:10.1021/ja02126a001. 
4. ^ H. Bauer (1980). "Die ersten organisch-chemischen Synthesen". Naturwissenschaften 67 (1): 1 -6. DOI:10.1007/BF00424496. 
5. ^ J. Gay-Lussac (1815). "?". Ann. chim. et phys. 96: 175. 
6. ^ Muir, GD (ed.) 1971, Hazards in the Chemical Laboratory, The Royal Institute of Chemistry, London.
7. ^ Thomas, N. & Gaydon, A. G.; Brewer, L. (March 1952), "Cyanogen Flames and the Dissociation Energy of N2", The Journal of Chemical Physics 20 (3): 369-374, <[2]

External links

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
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Color or colour[1] (see spelling differences) is the visual perceptual property corresponding in humans to the categories called red, yellow, blue, black, etc.
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Gas is one of the four major states of matter, consisting of freely moving atoms or molecules without a definite shape. Compared to the solid and liquid states of matter a gas has lower density and a lower viscosity.
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Pungency is a sharp and biting sensory impression. Regarding chili peppers, it refers to a scientific equivalent of the Scoville scale of measuring spicyness.

Mechanism


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odor or odour (see spelling differences) is a volatilized chemical compound, generally at a very low concentration, which humans and other animals perceive by the sense of olfaction. Odors are also called smells, which can refer to both pleasant and unpleasant odors.
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Pseudohalogens are binary inorganic compounds of the general form XY, where X is a cyanide, cyanate, thiocyanate etc. group and Y is any of X, or a true halogen. Not all combinations are known to be stable. Examples include cyanogen, (CN)2, and iodine cyanide, ICN.
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1, 3, 5, 7
(strongly acidic oxide)
Electronegativity 3.16 (Pauling scale)
Ionization energies
(more) 1st: 1251.2 kJmol−1
2nd: 2298 kJmol−1
3rd: 3822 kJmol−1

Atomic radius 100 pm
Atomic radius (calc.
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cyanide ion, CN−.
From the top:
1. Valence-bond structure
2. Space-filling model
3. Electrostatic potential surface
4. 'Carbon lone pair' HOMO]] A cyanide
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
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Cyanogen bromide is a chemical compound with the formula CNBr. It is colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds.
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In chemistry, an anhydride is a compound that can be considered as derived from another compound by subtracting the molecules of water.

For example:

2 NaOH - H2O = Na2O
H2SO4 - H2

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Oxamide is a white crystalline solid, which is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Heating it in air to temperatures above 350°C causes decomposition yielding cyanogen and water. Oxamide is the double amide of oxalic acid.
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Copper(II) sulfate ("sulphate" in most Commonwealth nations) is the chemical compound with the formula CuSO4. This salt exists as a series of compounds that differ in their degree of hydration.
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Copper(I) cyanide (CuCN), also copper cyanide, cuprous cyanide, or cupricin (CAS number [ 544-92-3 ], EINECS number 208-883-6) is a white to cream colored or sometimes greenish powdery solid that is insoluble
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Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, very poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C (78.8 °F).
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1, 3, 5, 7
(strongly acidic oxide)
Electronegativity 3.16 (Pauling scale)
Ionization energies
(more) 1st: 1251.2 kJmol−1
2nd: 2298 kJmol−1
3rd: 3822 kJmol−1

Atomic radius 100 pm
Atomic radius (calc.
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silicon dioxide, also known as silica or silox (from the Latin "silex"), is the oxide of silicon, chemical formula SiO2, and has been known for its hardness since the 16th century.
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catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance called a catalyst, which is itself not consumed by the overall reaction.
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Nitrogen dioxide is the chemical compound NO2. It is one of the several nitrogen oxides. This reddish-brown gas has a characteristic sharp, biting odor. NO2 is one of the most prominent air pollutants and a poison by inhalation.
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2, 1
(mildly basic oxide)
Electronegativity 1.90 (Pauling scale)
Ionization energies
(more) 1st: 745.5 kJmol−1
2nd: 1957.9 kJmol−1
3rd: 3666 kJmol−1

Atomic radius 135 pm
Atomic radius (calc.
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
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