Information about Nitro Compound
)
The structure of the nitro group
Aromatic nitro compounds are typically synthesized by the action of a mixture of nitric and sulfuric acids on a suitable organic molecule. Some examples of such compounds are trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). Chloramphenicol is a rare example of a naturally occurring nitro compound.
Preparation
In organic synthesis various methods exists to prepare nitro compounds.Aliphatic nitro compounds
- Nitromethane adds to aldehydes in 1,2-addition in the nitroaldol reaction
- Nitromethane adds to alpha-beta unsaturated carbonyl compounds as a 1,4-addition in the Michael reaction as a Michael donor
- Nitroethylene is a Michael acceptor in a Michael reaction with enolate compounds
- In nucleophilic aliphatic substitution sodium nitrite (NaNO2) replaces an alkyl halide. In the so-called ter Meer reaction (1876)
The ter Meer reaction
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- In one study, a reaction mechanism is proposed in which in the first slow step a proton is abstracted from nitroalkane 1 to a carbanion 2 followed by isomerization to a sodium nitronate 3 and finally nucleophilic displacement of chlorine based on an experimentally observed kinetic isotope effect of 3.3 [2]. When the same reactant is reacted with potassium hydroxide the reaction product is the 1,2-dinitro dimer [3]
Aromatic nitro compounds
- In electrophilic substitution nitric acid reacts with aromatic compounds in nitration
- A classic method starting from halogenated phenols is the Zinke nitration
Reactions
Nitro compounds participate in several organic reactions.Aliphatic nitro compounds
- Aliphatic nitro compounds are reduced to amines with hydrochloric acid and an iron catalyst
- Nitronates form by adding acids to nitro salts.
- Hydrolysis of the salts of nitro compounds yield aldehydes or ketones in the Nef reaction
Aromatic nitro compounds
- Reduction of aromatic nitro compounds with hydrogen gas over a platinum catalyst gives anilines.
- The presence of nitro groups facilitates nucleophilic aromatic substitution.
See also
References
1. ^ Edm. ter Meer (1876). "Ueber Dinitroverbindungen der Fettreihe". Justus Liebigs Annalen der Chemie 181 (1): 1 - 22. DOI:10.1002/jlac.18761810102.
2. ^ aci-Nitroalkanes. I. The Mechanism of the ter Meer Reaction M. Frederick Hawthorne J. Am. Chem. Soc.; 1956; 78(19) pp 4980 - 4984; doi:10.1021/ja01600a048
3. ^ 3-Hexene, 3,4-dinitro- D. E. Bisgrove, J. F. Brown, Jr., and L. B. Clapp. Organic Syntheses, Coll. Vol. 4, p.372 (1963); Vol. 37, p.23 (1957). (Article)
2. ^ aci-Nitroalkanes. I. The Mechanism of the ter Meer Reaction M. Frederick Hawthorne J. Am. Chem. Soc.; 1956; 78(19) pp 4980 - 4984; doi:10.1021/ja01600a048
3. ^ 3-Hexene, 3,4-dinitro- D. E. Bisgrove, J. F. Brown, Jr., and L. B. Clapp. Organic Syntheses, Coll. Vol. 4, p.372 (1963); Vol. 37, p.23 (1957). (Article)
Functional group |
|---|
| Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Disulfide • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioester • Thioether • Thiol |
organic compounds]] An organic compound is any member of a large class of chemical compounds whose molecules contain carbon; for historical reasons discussed below, a few types of compounds such as carbonates, carbon oxides and cyanides, as well as elemental carbon are
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In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules.
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1
Atomic radius 65 pm
Atomic radius (calc.
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(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1
Atomic radius 65 pm
Atomic radius (calc.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1
Atomic radius 60 pm
Atomic radius (calc.
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(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1
Atomic radius 60 pm
Atomic radius (calc.
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explosive material is a material that either is chemically or otherwise energetically unstable or produces a sudden expansion of the material usually accompanied by the production of heat and large changes in pressure (and typically also a flash and/or loud noise) upon initiation;
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exothermic reaction is one that releases heat. It is the opposite of an endothermic reaction. Expressed in a chemical equation:
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Overview
In an exothermic reaction, the total energy absorbed in bond breaking is less than the total energy released..... Click the link for more information.
For the airport with the IATA airport code TNP, see .
Picric acid is the chemical compound more formally called 2,4,6-trinitrophenol. This a yellow crystalline solid is one of the most acidic phenols.
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Trinitrotoluene (TNT) is a chemical compound with the formula C6H2(NO2)3CH3. This yellow-coloured solid is a reagent (reactant) in chemistry but is best known as a useful explosive material with convenient handling
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Styphnic acid, or 2,4,6-trinitro-1,3-benzenediol, is a yellow astringent acid that forms hexagonal crystals. It is used in the manufacture of dyes, pigments, inks, medicines, and explosives such as lead styphnate. It is itself a sensitive explosive, similar to picric acid.
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Chloramphenicol is a bacteriostatic antimicrobial originally derived from the bacterium Streptomyces venezuelae, isolated by David Gottlieb, and introduced into clinical practice in 1949.
It was the first antibiotic to be manufactured synthetically on a large scale.
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It was the first antibiotic to be manufactured synthetically on a large scale.
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Organic synthesis is the construction of organic molecules via chemical processes. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has developed into one of the most important aspects of
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Nitromethane is an organic compound with the chemical formula CH3NO2. It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a
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aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom which is bonded to a hydrogen atom and double-bonded to an oxygen atom (chemical formula O=CH-), is called the aldehyde group.
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The Nitroaldol reaction or Henry reaction [1] is an aldol type reaction between an aldehyde and nitromethane. The nucleophilic addition step is base catalysed and may be followed by an elimination reaction with removal of water when an acidic alpha proton is
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The Michael reaction or Michael addition is the nucleophilic addition of an carbanion to an alpha, beta unsaturated carbonyl compound. It belongs to the larger class of conjugate additions. This is one of the most useful methods for the mild formation of C-C bonds.
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The Michael reaction or Michael addition is the nucleophilic addition of an carbanion to an alpha, beta unsaturated carbonyl compound. It belongs to the larger class of conjugate additions. This is one of the most useful methods for the mild formation of C-C bonds.
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Enols (also known as alkenols) are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds (such as ketones and aldehydes) are in fact isomers; this is called keto-enol tautomerism:
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Sodium nitrite, with chemical formula NaNO2, is used as a color fixative and preservative in meats and fish. When pure, it is a white to slight yellowish crystalline powder. It is very soluble in water and is hygroscopic.
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haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide.
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In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs.
Although only the net chemical change is directly observable for most chemical reactions, experiments can often be designed that suggest the
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Although only the net chemical change is directly observable for most chemical reactions, experiments can often be designed that suggest the
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In chemistry, hydronium is the common name for the cation H3O+ derived from protonation of water. It is the simplest type of an oxonium ion.
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Nomenclature
According to IUPAC ion nomenclature, the hydronium ion should be referred to as..... Click the link for more information.
A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons [1]. The carbanion exists in a trigonal pyramidal geometry.
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In chemistry, isomerization or isomerisation is the transformation of a molecule into a different isomer [1]. In some molecules and under some conditions, isomerisation occurs spontaneously.
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A nitronate in organic chemistry is a functional group with the general structure R1R2C=N+(OH)(O-). It is a tautomeric form of a nitro group. A nitronate is also called a aci form.
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In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of substitution reaction in which an "electron rich" nucleophile selectively bonds with or attacks the positive charge of a group or atom called the leaving group; rarely referred to as an
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The kinetic isotope effect (KIE) is a variation in the reaction rate of a chemical reaction when an atom in one of the reactants is replaced by one of its isotopes. It is also called isotope fractionation, although this term is technically somewhat broader in meaning.
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The chemical compound potassium hydroxide (KOH), sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base.
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Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen. Electrophilic substitution is characteristic of aromatic compounds.
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The chemical compound nitric acid (HNO3), also known as aqua fortis and spirit of nitre, is an aqueous solution of hydrogen nitrate (anhydrous nitric acid). It is a highly corrosive and toxic acid that can cause severe burns.
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Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone.
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