Carbon oxohalides are a group of chemical compounds that contain only carbon, oxygen and halogen atoms: fluorine, chlorine, bromine and iodine. They include carbonyl halides, COX2, and oxalyl halides, C2X2O2, where X = F, Cl, Br or I. The halogen atoms X do not have to be identical; they differ in mixed oxohalides. Most combinations of halogens exist but carbonyl iodide, COI2, is unknown. The carbon–oxygen bond length in carbonyl halides (1.13–1.17 Å)[1] is shorter than in other carbonyl compounds[2] such as aldehydes and ketones, carboxylic acids, esters and amides (1.20–1.21 Å).[3] They are reactive reagents for halogenation,[1] acylation and dehydration reactions.[4]
Carbon oxohalides[1]
Name
Formula
Melting point / °C
Boiling point / °C
C–O bond length / Å
Carbonyl fluoride
COF2
−114
−83.1
1.174
Carbonyl chloride fluoride
COFCl
−42
Carbonyl bromide fluoride
COFBr
−20.6
Phosgene
COCl2
−127.8
+7.6
1.166
Carbonyl iodide fluoride
COFI
−90
+23.4
Carbonyl bromide chloride
COClBr
Carbonyl bromide
COBr2
+64.5
1.13
Oxalyl fluoride
C2F2O2
−3
+26.6
Oxalyl chloride
C2Cl2O2
−16
+63
Diphosgene
C2Cl4O2
−57
+128
Triphosgene
C3Cl6O3
+80
+206
^ abcGreenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 304–305. ISBN 978-0-08-037941-8.
^Wells, A. F. (1984). Structural Inorganic Chemistry (5th ed.). Oxford University Press. p. 917. ISBN 978-0-19-965763-6.
^David R. Lide, ed. (1995). CRC Handbook of Chemistry and Physics (84th ed.). CRC Press. p. 9-34. ISBN 978-0849304842.
^Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. pp. 724, 728, 1276, 1427, 1550. ISBN 978-0-471-72091-1.
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