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.[1]

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. ^ a b 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.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.