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nitrosobenzene
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Nitrosobenzene is the organic compound with the formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale yellow dimer. Both monomer and dimer are diamagnetic.
Chemical data
- Formula
- C6H5NO
- Molecular weight
- 107.11 g/mol
- IUPAC name
- nitrosobenzene
- SMILES
- C1=CC=C(C=C1)N=O
- InChIKey
- NLRKCXQQSUWLCH-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 29.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 112.06849750999999
Show 3 more facts
- chemical formula
- C₆H₅NO
- canonical SMILES
- C1=CC=C(C=C1)N=O
- isomeric SMILES
- [2H]C1=C(C(=C(C(=C1[2H])[2H])N=O)[2H])[2H]
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Monomer-dimer equilibrium
- Preparation
- Characteristic reactions
- Lewis basicity
- References
Nitrosobenzene is the organic compound with the formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale yellow dimer. Both monomer and dimer are diamagnetic.
==Monomer-dimer equilibrium== Nitrosobenzene and other nitrosoarenes typically participate in a monomer-dimer equilibrium. The dimers are often favored in the solid state, whereas the deeply colored monomers are favored in dilute solution or at higher temperatures. The dimers can be formulated as Ar(O−)N+=N+(O−)Ar. They exist as cis- and trans-isomers due to the presence of the N–N double bond. The dimers are sometimes called azobenzenedioxides. The cis-trans isomerization occurs via the intermediacy of the monomer.
Excerpted from Wikipedia’s “nitrosobenzene” article, available under the CC BY-SA 4.0 licence.