Properties of the Nitro Group

X-ray measurements show the nitrobenzene molecule to be completely planar [18]. Resonance theory pictures nitrobenzene as a superimposition of four structures  

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Construction of the carbon frameworks by using the activating property of the nitro group followed by denitration provides a useful tool for the preparation of various naniral products as shovm in Schemes 3 5-3 7 For example, fZ -jasmone and dihydrojasmone, constinients of the essential oilof jasmone flowers, have been prepared as shown in Scheme 3 5 Schemes 3 6 and 3 7 present a synthesis of pheromones via denitration of ct-nitro ketones " ... 

The chemical properties of the nitro group have important implications for the synthesis of more complex and useful polynitroaliphatic compounds and so these issues are discussed in relation to energetic materials synthesis. 

As a consequence of the strong electron-withdrawing properties of the nitro group, conjugated nitroalkenes behave as powerful Michael acceptors. An example of conjugate addition of Reformatsky reagents to (2-nitrovinyl)arenes 107 is given in equation 63150. 

In the first method, nitrating first then brominating would give predominantly the meta isomer of the final product because of the meta directing properties of the nitro group. The second method is better as the directing properties of bromine are favourable to us. Hence, we would have to separate the para product from the ortho product but we would still get a higher yield by this route. 

X 10 , and 10 x 10 , respectively, indicating the electron-attracting property of the nitro group. 2-Hydroxyquinazoline is hydrated to the extent of about 25% in the neutral species. ... 

In addition, Seebach has extended his work on nitroallyl pivalates as multicoupling reagents (Vol. 6, p. 208) and has now published the synthesis and reactions of the nitroallyl pivalates (22) and (23) and the chloride (24) (Scheme 35). These new reagents furnish adducts with a variety of nucleophilic species and, as with previously reported analogues, the acceptor properties of the nitro-group may be further exploited. 

Janz and Danyluk referred to liquids such as nitrobenzene as nonbasic, although that compound was described as polar. The weakly acidic properties of the nitro group were said to limit the utility of nitrobenzene and nitromethane as ionizing media for the hydrogen halides. It was also stated that hydrogen chloride and hydrogen bromide are very weak electrolytes in acetic acid. 

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