Pseudohalogens are polyatomic analogues of halogens, whose chemistry, resembling that of the true halogens, allows them to substitute for halogens in several classes of chemical compounds.[1] Pseudohalogens occur in pseudohalogen molecules, inorganic molecules of the general forms Ps–Ps or Ps–X (where Ps is a pseudohalogen group), such as cyanogen; pseudohalide anions, such as cyanide ion; inorganic acids, such as hydrogen cyanide; as ligands in coordination complexes, such as ferricyanide; and as functional groups in organic molecules, such as the nitrile group. Well-known pseudohalogen functional groups include cyanide, cyanate, thiocyanate, and azide.
Common pseudohalogens and their nomenclature[edit]
Many pseudohalogens are known by specialized common names according to where they occur in a compound. Well-known ones include (the true halogen chlorine is listed for comparison):
Group | Dimer | Hydrogen compound | Pseudohalide | Ligand name | In organic compounds | Formula | Structural formula |
---|---|---|---|---|---|---|---|
chloro | chlorine | hydrochloride | chloride | chlorido- chloro- | -yl chloride | ~ Cl | −Cl |
cyano | cyanogen | hydrogen cyanide, prussic acid, formonitrile | cyanide | cyanido- cyano- | -nitrile -yl cyanide | ~ CN | −C≡N |
cyapho | cyaphogen | phosphaethyne | cyaphide | cyaphido- cyapho- | -yl cyaphide | ~ CP | −C≡P |
isocyano | hydrogen isocyanide, isohydrocyanic acid | isocyanide | isocyanido- isocyano- | -isonitrile -yl isocyanide | ~ NC | −N+ ≡C− | |
hydroxyl | hydrogen peroxide | water | hydroxide | hydroxido- hydroxy- | -ol | ~ OH | −O−H |
sulfanyl | hydrogen disulfide | hydrogen sulfide | hydrosulfide | sulfanido- thiolato- | -thiol -yl mercaptane | ~ SH | −S−H |
cyanate | cyanic acid | cyanate | cyanato- | -yl cyanate | ~ OCN | −O−C≡N | |
isocyanate | diisocyanogen | isocyanic acid | isocyanate | isocyanato- | -yl isocyanate | ~ NCO | −N=C=O |
fulminate | fulminic acid | fulminate | fulminato- | -nitrile oxide -yl fulminate | ~ CNO | −C≡N+ –O− | |
thiocyanate, rhodanide | thiocyanogen | thiocyanic acid | thiocyanate | thiocyanato- | -yl thiocyanate | ~ SCN | −S−C≡N |
isothiocyanate | isothiocyanic acid | isothiocyanate | isothiocyanato- | -yl isothiocyanate | ~ NCS | −N=C=S | |
selenocyanate, selenorhodanide | selenocyanogen | selenocyanic acid | selenocyanate | ~ SeCN | −Se−C≡N | ||
tellurocyanate,[2] tellurorhodanide | tellurocyanogen | tellurocyanic acid | tellurocyanate | ~ TeCN | −Te−C≡N | ||
azide | hexazine | hydrazoic acid | azide | azido- | -yl azide | ~ N3 | −N− −N+ ≡N ↕ −N=N+ =N− |
nitrogen monoxide | dinitrogen dioxide | nitroxyl | nitrosyl | nitroso- | ~ NO | •N=O | |
nitrogen dioxide | nitrogen tetroxide | nitryl | nitro- | ~ NO2 | −NO2 | ||
cobalt carbonyl | dicobalt octacarbonyl | cobalt tetracarbonyl hydride | tetracarbonylcobaltate | ~ Co(CO)4 | −Co(C≡O)4 | ||
trinitromethanide | hexanitroethane | nitroform, trinitromethane | trinitromethanide | trinitromethanido- | -yl trinitromethanide | ~ C(NO2)3 | −C(NO2)3 |
tricyanomethanide | hexacyanoethane | cyanoform, tricyanomethane | tricyanomethanide | tricyanomethanido- | -yl tricyanomethanide | ~ C(CN)3 | −C(CN)3 |
https://en.wikipedia.org/wiki/Pseudohalogen
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