Nitro Compounds, Aromatic

Abstract

The article contains sections titled: 1. Introduction 2. Nitration 2.1. Nitrating Agents 2.2. Reaction Mechanisms 3. Nitro Aromatics 3.1. Nitrobenzenes 3.2. Nitrotoluenes 3.3. Nitroxylenes 3.4. Nitronaphthalenes 3.5. Other Nitro Aromatics 4. Nitrohalo Aromatics 4.1. Chloronitrobenzenes 4.2. Dichloro‐ and Polychloronitrobenzenes 4.3. Chloronitrotoluenes 4.4. Fluoronitrobenzenes and Fluoronitrotoluenes 5. Nitroamino Aromatics 5.1. Nitroanilines 5.2. Nitrotoluidines 5.3. Halogenonitroanilines 5.4. Cyanonitroanilines 6. Nitroaromatic Sulfonic Acids and Derivatives 6.1. Nitrobenzenesulfonic acids and Derivatives 6.2. Nitrotoluenesulfonic Acids and Derivatives 6.3. Chloronitrobenzenesulfonic Acids and Derivatives 6.4. Chloronitrotoluenesulfonic Acids 7. Nitrohydroxy and Alkoxy Aromatics 7.1. Nitrophenols and Derived Ethers 7.2. Nitroalkylphenols 8. Nitroketones 9. Nitroheterocycles 9.1. Pyridine Derivatives 9.2. Quinoline Derivatives 9.3. Imidazole Derivatives 9.4. Furan Derivatives 9.5. Thiophene Derivatives 9.6. Thiazole Derivatives

Structural, Functional, and Spectroscopic Characterization of the Substrate Scope of the Novel Nitrating Cytochrome P450 TxtE

“…Conventional methods for the nitration of organic compounds employ harsh reaction conditions, most commonly direct aromatic nitration utilizing nitric and sulfuric acids. [4–6] Oxidation is a common side reaction under these conditions and formation and isolation of the desired isomer can be intractable depending on the complexity of the substrate. In contrast, biological nitration typically proceeds through the oxidation of an amine or, to a lesser extent, through unselective and/or inefficient direct aromatic nitration.…”

Electroanalysis of Nitro and Amino Derivatives of Polycyclic Aromatic Hydrocarbons

“…Therefore, nitrobenzene (17) represents a suitable model substance for description and discussion of electrochemical transformations of the nitro group at most of the NPAHs, not only because of it was the first organic compound studied by polarography in 1925 [98]. The schematic pathways of these electrochemical transformations of the nitro group at nitrobenzene (17) are shown in Scheme 1 [97,99].…”

“…Nitrobenzene (17)(18) is reduced in aqueous medium at mercury, gold or molybdenum electrodes at low pH in two waves/peaks, and at high pH in one wave/peak [103][104][105]. Cyclic voltammetry (CV) in neutral buffer gives a four-electron reduction peak to hydroxylaminobenzene (26)(27)(28), which is on the anodic sweep re-oxidized to nitrosobenzene (23)(24); on the second cathodic sweep the reduction of nitrosobenzene (24) is observed.…”

“…For NPAHs, such voltammetric behavior is also observable at mercury electrodes, partly as intramolecular [113] and partly as intermolecular (e.g., in 2,2'-dinitrobiphenyl (10) [114,115]) interactions during transformations of the nitro groups in the protic media. CV of nitrobenzene (17) in the presence of sodium dodecyl sulfate or high concentrations of N,N-dimethylformamide (DMF) gives a one-electron peak (formation of the nitro anion radical (19)) followed by a three-electron peak (formation of the hydroxylamine (26)), whereas in the presence of cationic or neutral surfactants, a four-electron peak is found at the hanging mercury drop electrode (HMDE) [110][111][112].…”

“…Further uses, such as use as a deblooming agent for petroleum and oils and as a component in the formulation of explosives, are of historical interest only. 1,5-Dinitronaphthalene (5) and 1,8-dinitronaphthalene (6) are used as intermediates in the production of sensitizing agents for ammonium nitrate explosives or colorant intermediates for naphthoperinones synthesis [17]. Nevertheless, the industrial production of NPAHs is negligible in comparison with the total volume of chemicals produced worldwide and may contribute more significantly only to local pollution.…”