Azobenzene dioxide

Azobenzene dioxide is the organic compound with the formula (C6H5N(O))2. Both cis and trans isomers are known. The cis isomer has been crystallized. It is colorless.[1]

Azobenzene dioxide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H10N2O2/c1-2-4-8(5-3-1)13-14-12-7-6-9-10(15-9)11(12)16-12/h1-7,9-11H
    Key: CDTVSBIIRCYWTM-UHFFFAOYSA-N
  • cis: InChI=1S/C12H10N2O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H/b14-13+
    Key: WHFNSVMCGRQIRC-BUHFOSPRSA-N
  • C1=CC=C(C=C1)N(=O)=N(=O)C2=CC=CC=C2
Properties
C12H10N2O2
Molar mass 214.224 g·mol−1
Appearance colorless solid
Density 1.31 g/cm3
Melting point 68 °C (154 °F; 341 K) with decomposition to the monomer
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions
Structure of (PhNO)2 viewed down an approximate C2 axis. The N-O and N-N distances are 1.26 (average of two) and 1.33 Å, respectively.[1] Color code: blue=N, red = O, gray = C.

When dissolved, azobenzene dioxide converts to deeply blue nitrosobenzene:

(C6H5N(O))2 → 2 C6H5NO

Azobenzene dioxide is a weak base, forming coordination complexes such as [Co[(C6H5N(O))2]4]2+.[2]

References
  1. Dieterich, David A.; Paul, Iain C.; Curtin, David Y. (1974). "Structural studies on nitrosobenzene and 2-nitrosobenzoic acid. Crystal and molecular structures of cis-azobenzene dioxide and trans-2,2'-dicarboxyazobenzene dioxide". Journal of the American Chemical Society. 96 (20): 6372–6380. doi:10.1021/ja00827a021.
  2. Emhoff, Kylin A.; Balaraman, Lakshmi; Simpson, Sydney R.; Stromyer, Michael L.; Kalil, Haitham F.; Beemiller, James R.; Sikatzki, Philipp; Eshelman, Teya S.; Salem, Ahmed M. H.; Debord, Michael A.; Panzner, Matthew J.; Youngs, Wiley J.; Boyd, W. Christopher (2018). "Synthesis and Characterization of Cobalt(II) N , N ′-Diphenylazodioxide Complexes". ACS Omega. 3 (11): 16021–16027. doi:10.1021/acsomega.8b01200. PMC 6643636. PMID 31458240.
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