1914] 



NITROGEN IN AMMONIUM SALTS. 



21 



guished from the others by a determination of the molecular weight 

 it is not clear how any of the ordinary physical methods could be 



.CO2 yCO^H 



used to distinguish between the three forms, R<^ , R<^ 



^NH3 ^NH30H 



.CO2 CO,H 



and R<^ . The form Rc^ would have a lower molecular 



weight and might, possibly, be distinguished from the other three 

 by that means. It does not seem to us that the ordinary equations 

 for hydrolysis, which Winkelblech attempts to apply, could be used 

 in a complex case of this sort. 



From the above summary it would seem that the evidence with 

 regard to inner salt formation is not altogether satisfactory and light 

 upon the question from an entirely different point of view is wel- 

 come. We think that we have secured this from a study of the 

 specific rotations of a series of amino acids derived from camphor. 

 The formulas and names of the compounds are given below. To 

 bring out the relationships more clearly the specific rotations given 

 for the salts are calculated to the basis of one gram of the free acid 

 in I c.c. of the solution instead of for one gram of the salt. 



CH2— CCCH,)— CO 



C(CH3), 



\ 



O 



CH,— CH- 



-NH, 



/ 



CH,— CCCHJ— CO 



C(CH3), 



CH.,— CH- 



NH 



Aminocamphonanic Acid. 

 (a)D = — 29.2°. 



CH.— C(CH.)— CO2H 



"I 



crcHs), 



I 



CH,— CH— NH3CI 

 Hydrochloride of Aminocam- 

 phonanic Acid. (a)o = 25.o°. 



Anhydride of Aminocampho- 

 nanic Acid. (a)D= — 60.5°. 



CH, 



CH2— C(CH3)NH3 

 C(CH3), 



\ 



-C(CH3)— CO^Na 

 C(CH3), 



CH,— CHNH, 

 Sodium Salt of Aminocampho- 

 nanic Acid. (0)0 = 52.8°. 



CH,— C(CH3)— NH 



O 



CH,— CHCO' 

 Aminodihydrocampholytic Acid. 

 (a)D = 53.7°. 



CiCH,), 



CH.— CH 



-CO 



Anhydride of Aminodihydrocam- 

 pholytic Acid. (a)7> = 72.8°. 



