2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane) is the
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
(CH
3)
3CNO. It is a blue liquid that is used in chemical research as a
spin trap, i.e. it binds to
radical
Radical (from Latin: ', root) may refer to:
Politics and ideology Politics
*Classical radicalism, the Radical Movement that began in late 18th century Britain and spread to continental Europe and Latin America in the 19th century
*Radical politics ...
s.
Preparation and structure
Many strong oxidants convert
''tert''-butylamine to the nitroso compound, but none do so in high yield. Consequently, ''t''-BuNO is prepared by the following "oscillatory redox" sequence:
:(CH
3)
3CNH
2 →
(CH3)3CNO2
:(CH
3)
3CNO
2 →
(CH3)3CNHOH
:(CH
3)
3CNHOH → (CH
3)
3CNO
The freshly distilled compound is a blue volatile liquid. Like other nitroso compounds, it features a bent C-N=O linkage. Upon standing at room temperature, the blue liquid converts to the colourless solid that is the dimer (m.p. 74-75 °C). In solution, this dimer quickly reverts to the blue monomer.
Reactions
It can be used as a
spin trap. This molecule traps unstable
free radicals
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired electron, unpaired valence electron.
With some exceptions, these unpaired electrons make radicals highly chemical reaction, chemi ...
to form stable
paramagnetic
Paramagnetism is a form of magnetism whereby some materials are weakly attracted by an externally applied magnetic field, and form internal, induced magnetic fields in the direction of the applied magnetic field. In contrast with this behavior, ...
nitroxide radicals that can be detected and analyzed by
electron spin resonance
Electron paramagnetic resonance (EPR) or electron spin resonance (ESR) spectroscopy is a method for studying materials that have unpaired electrons. The basic concepts of EPR are analogous to those of nuclear magnetic resonance (NMR), but the spin ...
spectroscopy. It is particularly useful for trapping carbon-centered tyrosyl radicals. It has also been used in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
as
electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively Electric charge, charged, have an ...
to transform
sulfones
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of ...
into
aldehydes
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
.
MNP is also an efficient regulator of the radical
polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
of
methyl methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula . This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
History
MMA ...
through the 'pseudoliving' chain mechanism.
[
]
See also
*
Nitroso
In organic chemistry, nitroso refers to a functional group in which the nitric oxide () group is attached to an organic moiety. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkanes; ), ''S''-nitros ...
References
{{DEFAULTSORT:Methyl-2-Nitrosopropane, 2-
Nitroso compounds
Tert-butyl compounds