Any molecule with a cyano group (?C≡N)
Chemical compound
In
chemistry
, a
cyanide
(from
Greek
kyanos
'
dark blue
') 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.
[1]
In
inorganic
cyanides, the cyanide group is present as the cyanide anion
?
C≡N
. This anion is
extremely poisonous
. Soluble
salts
such as
sodium cyanide
(NaCN) and
potassium cyanide
(KCN) are highly toxic.
[2]
Hydrocyanic acid
, also known as hydrogen cyanide, or HCN, is a highly
volatile
liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.
Organic
cyanides are usually called
nitriles
. In nitriles, the
?C≡N
group is linked by a single
covalent bond
to carbon. For example, in
acetonitrile
(
CH
3
?C≡N
), the cyanide group is bonded to
methyl
(
?CH
3
). Although nitriles generally do not release cyanide ions, the
cyanohydrins
do and are thus toxic.
Bonding
[
edit
]
The cyanide ion
?
C≡N
is
isoelectronic
with
carbon monoxide
?
C≡O
+
and with molecular
nitrogen
N≡N. A triple bond exists between C and N. The negative charge is concentrated on
carbon
C.
[3]
[4]
Occurrence
[
edit
]
In nature
[
edit
]
Cyanides are produced by certain
bacteria
,
fungi
, and
algae
. It is an
antifeedant
in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of
bitter almonds
,
apricots
,
apples
, and
peaches
.
[5]
Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to
sugar
molecules in the form of cyanogenic
glycosides
and defend the plant against
herbivores
.
Cassava
roots (also called manioc), an important
potato
-like food grown in tropical countries (and the base from which
tapioca
is made), also contain cyanogenic glycosides.
[6]
[7]
The
Madagascar
bamboo
Cathariostachys madagascariensis
produces cyanide as a deterrent to grazing. In response, the
golden bamboo lemur
, which eats the bamboo, has developed a high tolerance to cyanide.
The
hydrogenase
enzymes contain cyanide
ligands
attached to iron in their active sites. The biosynthesis of cyanide in the
NiFe hydrogenases
proceeds from
carbamoyl phosphate
, which converts to
cysteinyl
thiocyanate
, the
CN
?
donor.
[8]
Interstellar medium
[
edit
]
The
cyanide radical
?
CN has been identified in
interstellar space
.
[9]
Cyanogen
,
(CN)
2
, is used to measure the temperature of
interstellar gas clouds
.
[10]
Pyrolysis and combustion product
[
edit
]
Hydrogen cyanide is produced by the combustion or
pyrolysis
of certain materials under oxygen-deficient conditions. For example, it can be detected in the
exhaust
of
internal combustion engines
and
tobacco
smoke. Certain
plastics
, especially those derived from
acrylonitrile
, release hydrogen cyanide when heated or burnt.
[11]
Organic derivatives
[
edit
]
In
IUPAC nomenclature
,
organic compounds
that have a
?C≡N
functional group
are called
nitriles
.
[12]
[13]
An example of a nitrile is
acetonitrile
,
CH
3
?C≡N
. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl
?OH
and cyanide
?CN
bonded to the same carbon atom is called
cyanohydrin
(
R
2
C(OH)CN
). Unlike nitriles, cyanohydrins do release poisonous
hydrogen cyanide
.
Reactions
[
edit
]
Protonation
[
edit
]
Cyanide is basic. The p
K
a
of hydrogen cyanide is 9.21. Thus, addition of
acids
stronger than hydrogen cyanide to solutions of cyanide salts releases
hydrogen cyanide
.
Hydrolysis
[
edit
]
Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes
hydrolysis
to give
ammonia
and
formate
, which are far less toxic than cyanide:
[14]
- CN
?
+ 2 H
2
O → HCO
?
2
+ NH
3
Cyanide hydrolase
is an
enzyme
that catalyzes this reaction.
Alkylation
[
edit
]
Because of the cyanide anion's high
nucleophilicity
, cyano groups are readily introduced into organic molecules by displacement of a
halide
group (e.g., the
chloride
on
methyl chloride
). In general, organic cyanides are called nitriles. In organic synthesis, cyanide is a C-1
synthon
; i.e., it can be used to lengthen a carbon chain by one, while retaining the ability to be
functionalized
.
[15]
- RX + CN
?
→ RCN + X
?
Redox
[
edit
]
The cyanide ion is a
reductant
and is
oxidized
by strong
oxidizing agents
such as molecular
chlorine
(
Cl
2
),
hypochlorite
(
ClO
?
), and
hydrogen peroxide
(
H
2
O
2
). These oxidizers are used to destroy cyanides in
effluents
from
gold mining
.
[16]
[17]
[18]
Metal complexation
[
edit
]
The cyanide anion reacts with
transition metals
to form
M-CN bonds
. This reaction is the basis of cyanide's toxicity.
[19]
The high affinities of metals for this
anion
can be attributed to its negative charge, compactness, and ability to engage in π-bonding.
Among the most important cyanide coordination compounds are the
potassium ferrocyanide
and the pigment
Prussian blue
, which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.
[20]
Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to
blueprints
,
bluing
, and
cyanotypes
.
Manufacture
[
edit
]
The principal process used to manufacture cyanides is the
Andrussow process
in which gaseous
hydrogen cyanide
is produced from
methane
and
ammonia
in the presence of
oxygen
and a
platinum
catalyst
.
[21]
[22]
- 2 CH
4
+ 2 NH
3
+ 3 O
2
→ 2 HCN + 6 H
2
O
Sodium cyanide, the precursor to most cyanides, is produced by treating
hydrogen cyanide
with
sodium hydroxide
:
[14]
- HCN + NaOH → NaCN + H
2
O
Toxicity
[
edit
]
Many cyanides are highly toxic. The cyanide anion is an
inhibitor
of the
enzyme
cytochrome c oxidase
(also known as aa
3
), the fourth complex of the
electron transport chain
found in the
inner membrane
of the
mitochondria
of
eukaryotic
cells. It attaches to the iron within this protein. The binding of cyanide to this enzyme prevents transport of electrons from
cytochrome c
to oxygen. As a result, the electron transport chain is disrupted, meaning that the cell can no longer aerobically produce
ATP
for energy.
[23]
Tissues that depend highly on
aerobic respiration
, such as the
central nervous system
and the
heart
, are particularly affected. This is an example of
histotoxic hypoxia
.
[24]
The most hazardous compound is
hydrogen cyanide
, which is a gas and kills by inhalation. For this reason, an air respirator supplied by an external oxygen source must be worn when working with hydrogen cyanide.
[11]
Hydrogen cyanide is produced by adding acid to a solution containing a cyanide salt. Alkaline solutions of cyanide are safer to use because they do not evolve hydrogen cyanide gas. Hydrogen cyanide may be produced in the combustion of
polyurethanes
; for this reason, polyurethanes are not recommended for use in domestic and aircraft furniture. Oral ingestion of a small quantity of solid cyanide or a cyanide solution of as little as 200 mg, or exposure to airborne cyanide of 270
ppm
, is sufficient to cause death within minutes.
[24]
Organic
nitriles
do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as
trimethylsilyl cyanide
(CH
3
)
3
SiCN
readily release HCN or the cyanide ion upon contact with water.
[25]
Antidote
[
edit
]
Hydroxocobalamin
reacts with cyanide to form
cyanocobalamin
, which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.
[26]
An older cyanide antidote kit included administration of three substances:
amyl nitrite
pearls (administered by inhalation),
sodium nitrite
, and
sodium thiosulfate
. The goal of the antidote was to generate a large pool of
ferric
iron (
Fe
3+
) to compete for cyanide with cytochrome a
3
(so that cyanide will bind to the antidote rather than the enzyme). The
nitrites
oxidize
hemoglobin
to
methemoglobin
, which competes with cytochrome oxidase for the cyanide ion. Cyanmethemoglobin is formed and the
cytochrome oxidase
enzyme is restored. The major mechanism to remove the cyanide from the body is by enzymatic conversion to
thiocyanate
by the
mitochondrial
enzyme
rhodanese
. Thiocyanate is a relatively non-toxic molecule and is excreted by the kidneys. To accelerate this detoxification, sodium thiosulfate is administered to provide a sulfur donor for
rhodanese
, needed in order to produce thiocyanate.
[27]
Sensitivity
[
edit
]
Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity,
asthma
, or
bronchitis
. MRLs may be revised after sufficient data accumulates.
[28]
Applications
[
edit
]
Mining
[
edit
]
Cyanide is mainly produced for the
mining
of
silver
and
gold
: It helps dissolve these metals allowing separation from the other solids. In the
cyanide process
, finely ground high-grade ore is mixed with the cyanide (at a ratio of about 1:500 parts NaCN to ore); low-grade ores are stacked into heaps and sprayed with a cyanide solution (at a ratio of about 1:1000 parts NaCN to ore). The precious metals are complexed by the cyanide
anions
to form soluble derivatives, e.g.,
[Ag(CN)
2
]
?
(dicyanoargentate(I)) and
[Au(CN)
2
]
?
(dicyanoaurate(I)).
[14]
Silver is less
"noble"
than gold and often occurs as the sulfide, in which case redox is not invoked (no
O
2
is required). Instead, a displacement reaction occurs:
The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a
tailing pond
or spent heap, the recoverable gold having been removed. The metal is recovered from the "pregnant solution" by reduction with
zinc
dust or by
adsorption
onto
activated carbon
. This process can result in environmental and health problems. A number of
environmental disasters
have followed the overflow of tailing ponds at gold mines. Cyanide contamination of waterways has resulted in numerous cases of human and aquatic species mortality.
[29]
Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to
iron pyrite
(fool's gold), wherein half of the sulfur atoms are replaced by
arsenic
. Gold-containing arsenopyrite ores are similarly reactive toward inorganic cyanide.
[
citation needed
]
Industrial organic chemistry
[
edit
]
The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles.
Acyl cyanides
are produced from acyl chlorides and cyanide.
Cyanogen
,
cyanogen chloride
, and the trimer
cyanuric chloride
are derived from alkali metal cyanides.
Medical uses
[
edit
]
The cyanide compound
sodium nitroprusside
is used mainly in
clinical chemistry
to measure
urine
ketone bodies
mainly as a follow-up to
diabetic
patients. On occasion, it is used in emergency medical situations to produce a rapid decrease in
blood pressure
in humans; it is also used as a
vasodilator
in vascular research. The cobalt in artificial
vitamin B
12
contains a cyanide ligand as an artifact of the purification process; this must be removed by the body before the vitamin molecule can be activated for biochemical use. During
World War I
, a copper cyanide compound was briefly used by
Japanese
physicians for the treatment of
tuberculosis
and
leprosy
.
[30]
Illegal fishing and poaching
[
edit
]
Cyanides are illegally used to capture live fish near
coral reefs
for the
aquarium
and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.
[31]
Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.
[32]
Pest control
[
edit
]
M44 cyanide devices
are used in the United States to kill
coyotes
and other canids.
[33]
Cyanide is also used for pest control in
New Zealand
, particularly for
possums
, an
introduced marsupial that threatens the conservation of native species
and spreads
tuberculosis
amongst cattle. Possums can become bait shy but the use of pellets containing the cyanide reduces bait shyness. Cyanide has been known to kill native birds, including the endangered
kiwi
.
[34]
Cyanide is also effective for controlling the
dama wallaby
, another introduced marsupial pest in New Zealand.
[35]
A licence is required to store, handle and use cyanide in New Zealand.
Cyanides are used as
insecticides
for fumigating ships.
[36]
Cyanide salts are used for killing ants,
[37]
and have in some places been used as rat poison
[38]
(the less toxic poison
arsenic
is more common).
[39]
Niche uses
[
edit
]
Potassium ferrocyanide
is used to achieve a blue color on cast
bronze sculptures
during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry.
Cyanide is also used in
jewelry
-making and certain kinds of
photography
such as
sepia toning
.
Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.
[40]
[41]
Human poisoning
[
edit
]
Deliberate cyanide poisoning of humans has occurred many times throughout history.
[42]
Common salts such as
sodium cyanide
are involatile but water-soluble, so are poisonous by ingestion.
Hydrogen cyanide
is a gas, making it more indiscriminately dangerous, however it is lighter than air and rapidly disperses up into the atmosphere, which makes it ineffective as a
chemical weapon
. Poisoning by hydrogen cyanide is more effective in an enclosed space, such as a
gas chamber
. Most significantly, hydrogen cyanide released from pellets of
Zyklon-B
was used extensively in the
extermination camps
of
the Holocaust
.
Food additive
[
edit
]
Because of the high stability of their complexation with
iron
, ferrocyanides (
Sodium ferrocyanide
E535,
Potassium ferrocyanide
E536, and Calcium ferrocyanide E538
[43]
) do not decompose to lethal levels in the human body and are used in the food industry as, e.g., an
anticaking agent
in
table salt
.
[44]
Chemical tests for cyanide
[
edit
]
Cyanide is quantified by
potentiometric titration
, a method widely used in gold mining. It can also be determined by titration with silver ion.
Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.
[45]
Qualitative tests
[
edit
]
Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of
ferricyanide
.
[46]
Iron(II) sulfate
added to a solution of cyanide, such as the filtrate from the
sodium fusion test
, gives
prussian blue
. A solution of
para
-benzoquinone
in
DMSO
reacts with inorganic cyanide to form a cyano
phenol
, which is
fluorescent
. Illumination with a
UV light
gives a green/blue glow if the test is positive.
[47]
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[
edit
]
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- ^
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Archived
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from the original on 2022-10-10
. Retrieved
2 September
2016
.
Sodium cyanide was initially registered as a pesticide on December 23, 1947, to control ants on uncultivated agricultural and non-agricultural areas.
- ^
"Tariff Information, 1921: Hearings on General Tariff Revision Before the Committee on Ways and Means, House of Representatives"
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AbeBooks.com
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Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin ? especially in the fight against typhus.
- ^
"Deadliest Poisons Used by Man"
.
PlanetDeadly.com
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Taylorson, R.; Hendricks, SB (1973).
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Gail, Ernst; Gos, Stephen; Kulzer, Rupprecht; Lorosch, Jurgen; Rubo, Andreas; Sauer, Manfred (2004). "Cyano Compounds, Inorganic".
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Ganjeloo, A; Isom, GE; Morgan, RL; Way, JL (1980). "Fluorometric determination of cyanide in biological fluids with p-benzoquinone*1".
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