Azobenzene dioxide

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).

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.

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. 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{C6H5(O)NN(O)C6H5}4]2+.

References

  1. 1 2 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. Bibcode:1974JAChS..96.6372D. 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.