Nitrosobenzene
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| Nitrosobenzene | |
|---|---|
 |
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| General | |
| Systematic name | ? |
| Other names | ? |
| Molecular formula | C6H5NO |
| SMILES | O=Nc1ccccc1 |
| Molar mass | 107.11 g/mol |
| Appearance | ? |
| CAS number | 586-96-9 |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | 65-69 °C (? K) |
| Boiling point | 59 °C, 18 mm Hg |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ? °C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry |
? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Nitrosobenzene is the organic compound C6H5NO. The compound can be viewed as hybrid of singlet O2 and azobenzene. This diamagnetic species exists in equilibrium with its dimer.
Contents |
[edit] Preparation
C6H5NO was first reported by Adolf Baeyer in 1874, who prepared it by the reaction of diphenylmercury and nitrosylbromide, "Bringt man eine Loesung von NOBr in Benzol in eine Loesung von Quecksilberphenyl in Benzol …"
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- [C6H5]2Hg + BrNO → C6H5NO + C6H5HgBr
The modern synthesis entails reduction of nitrobenzene to phenylhydroxylamine, C6H5NHOH, which is then oxidized by K2Cr2O7. C6H5NO was also prepared by Caro via oxidation of aniline using peroxymonosulfuric acid, Caro's acid. It is usually purified by steam distillation, where it comes over as a green liquid that solidifes to a colorless solid.
[edit] Characteristic reactions
The monomer undergoes Diels-Alder reactions with dienes. Most characteristically nitrosobenzene condenses with "active" methylene and amine groups, e.g. of malonic esters. Condensation with anilines affords azobenzene derivatives (Mills reaction).
Reduction of PhNO produces C6H5NH2, as already determined by Baeyer.
[edit] See also
[edit] External links
[edit] References
- A. Baeyer "Nitrosobenzol und Nitrosonaphtalin" Chemische Berichte 1874, vol. 7, pp.1638–1640.
- G. H. Coleman, C. M. McCloskey, F. A. Stuart "Nitrosobenzene" Organic Syntheses, Coll. Vol. 3, p.668; Vol. 25, p.80
- N. Caro, Z. angew. Chem., volume 11, p 845ff (1898).
- H. D. Anspon, p-Phenylazobenzoic Acid" Organic Syntheses, Coll. Vol. 3, p.711; Vol. 25, p.86
- H. Yamamoto, N. Momiyama "Rich Chemistry of Nitroso Compounds" Chemical Communications 2005, pp.3514–3525.
- H. Feuer in S. Patai (ed.) "The Chemistry of the Nitro and Nitroso Groups Part 1," Wiley: New York. pp. 278-283 (Mills reaction)
