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XVIII. On a New Series of Bodies in which Nitrogen is substituted for Hydrogen. 
By Peter Geiess, Esq. Communicated by A. W. Hofmann. 
Received June 2, — Read June 16, 1864. 
In some former papers* I have had occasion to describe a peculiar class of nitrogen- 
compounds, obtained by the action of nitrous acid upon amido-compounds, by the 
exchange of some of the hydrogen of the latter for the nitrogen of the nitrous acid. 
This substitution may be effected in two different ways ; accordingly every amido-com- 
pound may give rise to two distinctly different series of bodies. By viewing the amido- 
compounds as constructed according to the general formula C r H y _ 2 (N H 3 )" O z f , the 
changes may be expressed as follows : — 
I- 2[€. H,_ 2 (N H 3 )" OJ +NH © 2 =€ 2a , H 2( ,_ 2) (NH 3 )" (N 2 )"0 2z +2 H 2 0. 
H. -G x H (y _ 2) (NH 3 )"© z +NH0 2 =G x H ( ,_ 2) (N 2 )0" 2 +2tI 2 O. 
In the first equation one atom of nitrogen is substituted for three atoms of hydrogen con- 
tained in two atoms of the amido-compound, but in the second the substitution affects 
only one atom of the latter. I have hitherto directed my attention more particularly to 
the members of the first group, whether derived from amido-acids (such as diazo-amido- 
benzoic acid), or whether corresponding to amido-bases (diazo-amidobenzol). The bodies 
which I now shall have to describe in this communication are derived according to the 
second of the above general equations, and I have restricted myself almost entirely to 
the study of those which can thus be obtained from aniline and similar bases. 
With regard to the chemical nature of these bodies, I may mention generally that 
they are capable of combining with acids and bases, but that their basic character 
preponderates. They are remarkable for the great variety of compounds which they 
* Ann. der Cliem. und Pharm. Rd. exiii. p. 201 ; Bd. cxvii. p. 1 ; Bd. cxxi. p. 257; Supplement I. 1861, 
p. 100. Proceedings of the Royal Society, vol. ix. p. 594 ; vol. x. p. 309. 
f Chemists are not agreed upon the rational constitution of amido-compounds. They are frequently referred 
to the ammonia-type, and almost as frequently to the same type to which the nitro-compounds from which they 
are derived belong. In the latter case the group NH 2 is considered as replacing one atom, or NH 3 as taking 
the place of two atoms of hydrogen. Aniline can thus he written in three different ways, and expressed by the 
three formulae. 
€ 6 H 5 (H 2 N)', 
G 6 H 4 (H 3 N)". 
V 
Phenylamine. 
v “ rv J 
Amidobenzol. 
Ammoniabenzol. 
The two latter formulae appear to me to be capable of explaining 
bodies in which nitrogen is substituted for hydrogen. 
in the most natural manner the formation of 
MDCCCLX1V. 
4 U 
