Pseudohalogen

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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.

Common pseudohalogens

Group Formula Structural formula Molecule Acid Pseudohalide Ligand name Organic suffix
cyano ~C≡N ~CN cyanogen hydrogen cyanide
prussic acid
cyanide cyanido-
cyano-
-nitrile
-yl cyanide
cyapho ~CP ~C≡P cyaphogen Methylidynephosphane
hydrocyaphic acid
cyaphide cyaphido-
cyapho-
-yl cyaphide
isocyano ~NC ~N≡C isocyano-formonitrile Hydrogen isocyanide
isohydrocyanic acid
isocyanide isocyanido-
isocyano-
-isonitrile
-yl isocyanide
hydroxyl ~OH ~O−H hydrogen peroxide water hydroxide
bioxide
hydroxido-
hydroxy-
-ol
sulfhydryl ~SH ~S−H hydrogen disulfide hydrogen sulfide hydrosulfide
bisulfide
sulfanido
thiolato
-thiol
cyanate ~OCN ~O−C≡N cyanic acid cyanate cyanato- -yl cyanate
isocyanate ~NCO ~N≡C−O isocyanic acid isocyanate isocyanato- isocyanate,
-yl isocyanate
fulminate ~CNO ~C≡N−O fulminic acid fulminate fulminato- fulminate,
-yl fulminate
thiocyanate,
rhodanide
~SCN ~S−C≡N thiocyanogen thiocyanic acid thiocyanate thiocyanato- -yl thiocyanate,
-yl isothiocyanate
isothiocyanate ~NCS ~N=C=S isothiocyanic acid isothiocyanate isothiocyanato- -yl isothiocyanate
hypothiocyanite ~OSCN hypothiocyanous acid hypothiocyanite thiocyanito- -yl hypothiocyanite
selenocyanate,
selenorhodanide
~SeCN ~Se−C≡N selenocyanogen selenocyanic acid selenocyanate
azide ~N3 ~N
N+
≡N

~N=N+
=N
hexazine hydrazoic acid azide azido- -yl azide
nitrogen dioxide ~NO2 dinitrogen tetroxide nitrous acid nitrite nitro- -yl nitrite
cobalt carbonyl ~Co(CO)4 ~Co(−C≡O)4 dicobalt octacarbonyl cobalt tetracarbonyl hydride tetracarbonylcobaltate(1−)  ?  ?
trinitromethanide C(NO2)3 C(NO2)3 trinitromethane trinitromethanide trinitromethanido- (IUPAC) trinitromethan,
-yl trinitromethanide
tricyanomethanide C(CN)3 C(CN)3 tricyanomethane tricyanomethanide tricyanomethanido- (IUPAC), tricyanomethanido- tricyanomethan,
-yl tricyanomethanide
trifluoromethanesulfonate ~O3SCF3 ~OTf triflic acid trifluoromethanesulfonate, triflate triflate (-yl) trilfate -yl triflate

Preparation

See the page for each compound.

See also

References

Relevant Sciencemadness threads