Aniline nitrate

Compare energies for meta and para-dinitrobenzenium ions (intermediates in nitration of nitrobenzene). Is the ordering the same as those observed for intermediates in toluene and aniline nitration Examine electrostatic potential maps. What does your result suggest about the electron donor/aceptor properties of the nitro substituent ... 

When nitrous gases (from arsenious oxide and nitric acid, d. 1 -35) are passed into a well-cooled suspension of aniline nitrate in water, and alcohol and ether are then added gradually, crystalline phenyldiazonium nitrate is obtained. At most only 2 g. of aniline are used, and of the diazonium salt only as much as covers well the tip of a knife-blade is dried on porous plate, after collecting at the pump and washing with alcohol-ether (1 1). 

Note According to Daniel(1902),pp 462-3, aniline nitrate served in France for the prepn of a primary compd, diazobenzene nitrate, known in France as aniline fulminmie. The reaction proceeded as follows ... 

Anilines, Nitrated, Analysis. Mononitroani-lines can be detd by methods described in Refs 4-7 9-10... 

The term nitrate is also used when HNOa combines directly with an organic molecule without replacing any H, as in aniline nitrate Many nitrated aromatic and aromatic-aliphatic derivs have been prepd and theoretically many more can be prepd. Numerous compds of these types, already prepd are expl, bur relatively few possess a combination of props which make them acceptable for use as military or industrial expls The individual nitrated compds are described in this work under what may be considered their parent compds eg TNT under toluene, PA (2,4,6-trinitrophenol) under phenol, etc... 

Delattre Explosive. The Societe anonyme pour la fabrication des cartouches et explosifs, Bruxelles, Belgium patented in 1898 the following compn Ba nitrate 78, aniline nitrate 12 Amm oxalate 10%... 

Owing to the highly explosive nature of the diazobenzene nitrate, its preparation should never be undertaken except the compound is wanted for research or some special purpose. 20 gms. of aniline are placed in a beaker, well cooled, and boiled-out nitric acid, previously diluted with half its volume of water, oarefully added till the mixture sets to a thick crystalline paste—aniline nitrate. The crystalline mass is filtered off at the pump, and washed with a little cold water. 5 gms. of the moist salt are finely powdered and placed in a small flask with enough water just to cover the substance. The flask is now well cooled in ice-water, and nitrous fumes (for preparation, see p. 513) are led in with frequent agitation until all the aniline nitrate has disappeared. At no time must the temperature of the flask rise above 10°. Should there not be sufficient water to keep all the diazobenzene nitrate formed in solution, its crystalline form will easily enable it to be distinguished from the aniline salt. When the reaction is finished the contents of the flask are poured into 3 times their volume of absolute alcohol, and ether is added to this mixture as long as crystals separate. If too much water has been added to the aniline nitrate from the beginning, a thick aqueous solution of diazobenzene nitrate separates out in place of the crystals. If this occurs, the ether-alcohol is decanted off, and the residue redissolved in absolute alcohol, and reprecipitated with ether. On no account must... 

The preparation of aniline nitrate is fully described on p. 375 under the preparation of diazobenzene nitrate. The crude product therein obtained is recrystallised by dissolving in a little absolute alcohol and precipitating therefrom with ether. The preparation and purification of aniline hydrochloride are exactly similar. 

The first volume of the Memorial des Poudres et Salpetres contains a report by Berthelot and Vieille04 on the properties of benzenediazonium nitrate (diazobenzene nitrate). They prepared the material by passing nitrous gas into a cooled aqueous solution of aniline nitrate, diluting with an equal volume of alcohol, and precipitating in the form of white, voluminous flocks by the addition of an excess of ether. 

Salts C8H5.NH2.HC1. . . . Aniline hydrochloride C6H5.NH .HN03. . . Aniline nitrate (CgH5. NHjJj. H2S04. . Aniline sulphate... 

Aniline hydrobromide Aniline hydrochloride Aniline nitrate... 

Chromosorb 102 Porapak Q Light and permanent gases, volatile carboxylic acids, alcohols, glycols, ketones, hydrocarbons, esters, nitriles and nitroalkanes. Not recommended for amines, anilines. Nitrated by nitrogen oxide gases. 

Aniline Aniline-2-carboxylicacid Aniline-3-carboxylic acid Aniline-4-carboxylicacid Aniline hydrobromide Aniline hydrochloride Aniline nitrate Aniline sulfate (2 1)... 

---