[ 97 ] 



VI. 



ON THE NITEO "DEEIVATIVES OF DIPHENYLAMINE. 



By HUGH RYAN, D.Sc, and THOMAS GLOVEE, M.Sc, 

 University College, Dublin. 



Read April 22. Published August 13, 1918. 



The study of the products formed by the action of nitric acid on diphenylamine, 

 beset as it is by many experimental difficulties, is rendered all the more 

 tedious by the existence in the chemical literature of discrepancies with 

 regard to the polynitro derivatives of the base. 



Thus 4-nitro-diphenylamine ' is described by 0. N. Witt (Ber. d. Dtsch. 

 Chem. Ges. xi (1878), p. 757) as orange leaves melting at 132"C, by Irma 

 Goldberg (D. B. P. 187870) as orange-red leaves melting at 133"C., by 

 E. Bamberger (Ber.d. Dtsch. Chem. Ges. xxxi (1898), p. 580) and F.Ullmann 

 (D.E.P. 193448) as yellow crystals, 



Picryl-aniline is described as red prisms by Clemm(Ber. iii(1870), p. 12G), 

 and as orange needles by E. Bamberger and Miiller (Ber. d. Dtsch. Chem. 

 Ges. xxxiii (1900), p. 108). 



Similarly for 2. 4. 8. 10-tetranitro-diphenylamine Hager (Ber. d. Dtsch. 

 Chem. Ges. xvii (1884), p. 2629) gives the melting-point as 1S0°C, A.Pietet and 

 E. Klein (Arch. d. Sciences phys. et nat., Geneve (4) xvi (1903), pp. 191-212; 

 as 197° C, Gnehm and Wys (Ber. d. Dtsch. Chem. Ges. x (1877), p. 1319) as 

 192° C, and P. Juillard (Bull. Soc. Chim., Paris (3) 1905, pp. 1172-1 190) as 

 199° C. 



For the removal of the discrepancies with regard to the properties of the 

 nitro- derivatives, and for the establishing of the constitutions of the latter 



'The numerical nomenclature of the diphenylamine derivatives discussed in this 

 communication is based on the formula 



/~% 2~\ /I 9 \ 



/., i\_nii-/7 10>- 



K.I. A. PROC, VOL. XXXIV, SECT. B. [0\ 



