70 PROCEEDINGS OF THE AMERICAN ACADEMY 



C6H(C6H5NH)(N02)3CNO,(COOC2H5)2, the nitrite of anilido- 

 trinitropheiiylauiloiiic ester, was obtained by the action of aniline on 

 the corresponding bromine compound ; it forms red rhombohedra, 

 which melt at 119°, decomposiug at one degree higher, and shows 

 marked acid properties, which must be due to the effect of the three 

 nitro groups upou the hydrogen attached to the nitrogen in the anilido 

 group, since, as has been already stated, the corresponding bromine 

 compound forms no salts. This conclusion was confirmed by the 

 study of the anilidotrinitrotoluol, which contains no other hydrogen 

 capable of being replaced by a basic radical, and yet formed the sodium 

 salt CGCH3H(C6H5NNa)(N02)3. As was to be expected, however, 

 this toluol compound was not so acid as the nitrite of anilidotrinitro- 

 phenylmalonic ester, which contains such a very negative radical in 

 place of the methyl. 



The anilidotrinitrotartronic ester was also made from the corre- 

 sponding bromine compound, and was obtained in two modifications ; 

 one formed at higher temperatures appeared in orange-red prisms 

 melting at 143°, the other in rounded masses of yellow needles melt- 

 ing at about 122°. Both show the same percentage composition on 

 analysis, and one is easily converted into the other ; the yellow into 

 the red by allowing the alcoholic solution to crystallize at about 60°, 

 by heating the solid a little below its melting point, or by boiling it 

 with water ; the red into the yellow by solution in glacial acetic acid 

 and precipitation with water. Unfortunately we have not succeeded in 

 determining the molecular weights of these substances, as we have 

 not yet found a solvent that gives satisfactor}' results with Raoult's 

 method. The work on these substances will be continued in this 

 laboratory, especially with a view to determining whether the nitrogen 

 is the cause of the isomerism (if they are not polymeres), but we may 

 say now that this does not seem very probable to us on account of the 

 striking resemblance in properties * between our two substances and 

 the two forms of benzilorthocarbonic acid described by Graebe.f 



The anilidotrinitrophcnyhartronic ester forms salts with one atom, 

 C6H(C6H5NH)(N02)3COM(COOC2H5)2, or with two atoms of uni- 

 valent basic radicals, CeH(CcH5NM)(NO,)3COM(COOCoH5)2. To 

 our great surprise, the disodic salt was formed even when the ester 

 was present in large excess. This tartronic ester is much more 

 strongly acid than the anilidotrinitrophenylmalonic ester (melting 



* It is a curious fact that even the melting points are nearly the same. 

 t Ber. d. ch. G., X.XIH. 1344. 



