生物化学23aromaticnitrogencompounds.pptVIP

Chapter 23 Aromatic Nitrogen Compounds §23.1 Nitroarenes 23.1.1 Structure of Nitrobenzene  23.1.2 Preparation of Nitrobenzene We have already seen many examples of the preparation of aromatic nitro compounds. By far the most important route to such compounds is electrophilic aromatic nitration with nitric acid. 23.1.3 Properties of Nitro Compounds Nitrobenzene and related nitro compounds are generally high boiling liquids. Nitrobenzene have a characteristic odor of almonds. Nitrobenzene is readily absorbed through the skin and is poisonous. 2,4,6-Trinitrotoluene,TNT, m.p. 81℃ TNT is an important explosive. It is relatively insensitive to shock and is used with a detonator(雷管, 炸药). 1,3,5-Trinitrobenzene is less sensitive than TNT to shock and has more explosive power, but is more difficult to prepare. 23.1.4 Reactions of Nitroarenes Reactivities of Nitro Group The nitro group is relatively stable to many reagents. It is generally inert to acids and most electrophilic reagents. It is also stable to most oxidizing agents. It reacts with RMgX and strongly basic reagents. The most important reaction of the nitro group in aromatic compounds is reduction. Reduction The reduction products depends on the reaction conditions used. Monomolecular Reductions of Nitroarenes In acid the intermediate compounds cannot be isolated, but are reduced rapidly in turn, In neutral media, a higher reduction potential is required and reduction is readily stopped at the hydroxylamine stage. 硝基苯还原关系图 Bimolecular Reductions of Nitroarenes 芳环上的亲核取代反应 Mechanism §23.2 Arylamines (Aromatic Amines) 23.2.1 Nomenclature Three common arylamines have the following names: 23.2.2 Physical Properties of Arylamines 23.2.3 Preparation of Arylamines 23.2.4 Basicity of Arylamines Arylamines are less basic than alkylamines because the nitrogen lonepair electrons are delocalized by orbital overlap with the aromatic ring pi electron system and are le