Thiocyanate

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Thiocyanate

Thiocyanate (also known as sulphocyanate or thiocyanide or rhodanide) is the anion, [SCN]^-. Common compounds include the colourless salts potassium thiocyanate

Potassium thiocyanate

Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides....
and sodium thiocyanate

Sodium thiocyanate

Sodium thiocyanate is the chemical compound with the formula NaSCN. This colourless deliquescent salt is one of the main sources of the thiocyanate anion....
. Organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s containing the functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
SCN are also called thiocyanates. Mercury(II) thiocyanate

Mercury(II) thiocyanate

Mercury thiocyanate is a chemical compound. It was formerly used in pyrotechnics for the long snake-like ash Pharaoh's serpent that forms when a pellet of this compound, often with a small amount of a sugar such as glucose added to serve as supplemental fuel, is ignited....
was formerly used in pyrotechnics.

Thiocyanate is analogous to the cyanate

Cyanate

The cyanate ion is an anion consisting of one oxygen atom, one carbon atom, and one nitrogen atom, [OCN]-, in that order, and possesses 1 unit of negative electric charge, borne mainly by the nitrogen atom....
ion, [OCN]^-, where in oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
is replaced by sulphur. [SCN]^- is one of the pseudohalide

Pseudohalogen

Pseudohalogens are binary inorganic Chemical compound of the general form XY, where X is a cyanide, cyanate, thiocyanate etc. group and Y is any of X, or a true halogen....
s, due to the similarity of its reactions to that of halide

Halide

A halide is a binary compound, of which one part is a halogen atom and the other part is an chemical element or radical that is less electronegative than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound....
ions.

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Encyclopedia

Thiocyanate (also known as sulphocyanate or thiocyanide or rhodanide) is the anion, [SCN]^-. Common compounds include the colourless salts potassium thiocyanate

Potassium thiocyanate

Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides....
and sodium thiocyanate

Sodium thiocyanate

Sodium thiocyanate is the chemical compound with the formula NaSCN. This colourless deliquescent salt is one of the main sources of the thiocyanate anion....
. Organic compound

Organic compound

Functional group

Mercury(II) thiocyanate

Cyanate

Oxygen

Pseudohalogen

Halide

Greek language

Greek is an Indo-European languages native to the southern Balkan peninsula, the language of the Greek people. It forms an independent branch within Indo-European....
word for rose

Rose

A rose is a perennial plant flower shrub or vine of the genus Rosa, within the family Rosaceae, that contains over 100 species and comes in a variety of colors....
) because of the red colour of its complexes with iron

Iron

Iron is a chemical element with the symbol Fe and atomic number 26. Iron is a Group 8 element and period 4 element. Iron is lustrous and silvery in color....
. Thiocyanate is produced by the reaction of elemental sulfur or thiosulfate

Thiosulfate

Thiosulfate is an oxyanion of sulfur produced by the reaction of sulfite ions with elemental sulfur in boiling water. Thiosulfate occurs naturally in hot springs and geysers, and is produced by certain biochemical processes....
with cyanide

Cyanide

A cyanide is any chemical compound that contains the nitrile , which consists of a carbon atom chemical bond to a nitrogen atom. Inorganic cyanides are hydrogen cyanide salts in which cyanide is generally the anion CN-....
:

8 CN^- + S₈ ? 8 SCN^-

CN^- + S₂O₃^2- ? SCN^- + SO₃^2-

The latter reaction is catalyzed by the enzyme sulfotransferase

Sulfotransferase

Sulfotransferases are transferase enzymes that catalyze the transfer of a sulfate group from a donor molecule to an acceptor alcohol or amine....
known as rhodanase

Rhodanase

Rhodanese is a mitochondrion enzyme which detoxifies cyanide by converting it to thiocyanate .This reaction takes place in two steps. The diagram on the right shows the X-ray crystallography-determined structure of rhodanese....
and may be relevant to detoxification of cyanide in the body.

Structure, bonding and coordination chemistry

Thiocyanate shares its negative charge approximately equally between sulfur and nitrogen. Consequently, thiocyanate can act as a nucleophile

Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
at either sulfur or nitrogen — it is an ambidentate ligand

Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
. [SCN]^- can also bridge two (M-SCN-M) or even three metals (>SCN- or -SCN<). Experimental evidence leads to the general conclusion that class a metals

Classes of metals

Class A metals are metals that form hard acids. Hard acids are acids with relatively ionic bonds. These metals, such as iron , aluminum, titanium, sodium, calcium and the lanthanides, would rather chemical bond with fluorine than iodine....
(hard acids

HSAB theory

Classes of metals

HSAB theory

The HSAB concept is an acronym for 'hard and soft acids and base s'. Also known as the Pearson acid base concept, HSAB is widely used in chemistry for explaining stability of chemical compound, chemical reaction mechanisms and pathways....
) tend to form S-bonded thiocyanate complexes. Other factors, e.g. kinetics and solubility, are sometimes involved, and linkage isomerism can occur, for example [Co(NH₃)₅(NCS)]Cl₂ and [Co(NH₃)₅(SCN)]Cl₂.

Organic thiocyanates

Organic and transition metal derivatives of the thiocyanate ion can exist as "linkage isomers." In thiocyanates, the organic group or metal is attached to sulfur: R-S-C=N has a S-C single bond and a C-N triple bond . In isothiocyanate

Isothiocyanate

Isothiocyanate is the chemical group -nitrogen=carbon=sulfur, formed by substituting sulfur for oxygen in the isocyanate group. Allyl isothiocyanate is a chemical compound found in mustard oil that is responsible for its pungency....
s, the substituent is attached to nitrogen: R-N=C=S has a S-C double bond and a C-N double bond

Organic thiocyanates are hydrolyzed to thiocarbamates in the Riemschneider thiocarbamate synthesis

Riemschneider thiocarbamate synthesis

The Riemschneider thiocarbamate synthesis produces aromatic thiocarbamates starting with the corresponding aromatic thiocyanate.The thiocyanate is treated with sulfuric acid and then hydrolyzed with ice water....
.

Test for iron(III)

If [SCN]^- is added to a solution containing iron(III) ions (Fe³⁺), a blood red solution is formed due to the presence of the [Fe(NCS)(H₂O)₅]²⁺.