二氧化偶氮苯

二氧化偶氮苯是一种有机化合物,化学式为(C
6
H
5
N(O))
2
,其顺式和反式异构体都是已知的。其中,顺式异构体是无色的晶体。[1]

二氧化偶氮苯
识别
CAS号 35506-28-6  checkY
31077-80-2Z checkY
115626-83-0E checkY
PubChem 135418545
SMILES
 
  • C1=CC=C(C=C1)N(=O)=N(=O)C2=CC=CC=C2
性质
化学式 C12H10N2O2
摩尔质量 214.22 g·mol−1
外观 无色固体
密度 1.31 g/cm3
熔点 68°C(分解)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

反应

 
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.

二氧化偶氮苯在溶解时会转化为深蓝色的亚硝基苯

(C
6
H
5
N(O))
2
→ 2 C
6
H
5
NO

它是一种弱碱,可以形成配离子,如[Co[(C
6
H
5
N(O))
2
]
4
]2+[2]

参考文献

  1. ^ 1.0 1.1 Dieterich, David A.; Paul, Iain C.; Curtin, David Y. 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. 1974, 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. Synthesis and Characterization of Cobalt(II) N , N ′-Diphenylazodioxide Complexes. ACS Omega. 2018, 3 (11): 16021–16027. PMC 6643636 . PMID 31458240. doi:10.1021/acsomega.8b01200. 

拓展阅读

  • Biljan, Ivana; Cvjetojevic, Gorana; Smrecki, Vilko; Novak, Predrag; Mali, Gregor; Plavec, Janez; Babic, Darko; Mihalic, Zlatko; Vancik, Hrvoj. Nitrosobenzene cross-dimerization: Structural selectivity in solution and in solid state. Journal of Molecular Structure (Elsevier BV). 2010, 979 (1-3): 22–26. ISSN 0022-2860. doi:10.1016/j.molstruc.2010.05.034.