22 



NOYES-POTTER— THE VALENCE OF 



[April 24, 



CH,— C(CH3)NH3C1 



C(CH3), 

 CH2— CHCO2H 



Hydrochloride of Aminodihy- 

 drocampholytic Acid. 



CH,— C(OH3)— CO^H 



C(OH3), 



I 

 CH2— CH— CHoNH, 



a-Aminocampholic Acid. 

 (a)D = 67°. 



CH,— C(CH3)— CO^H 



CiCHg), 

 CH.— CH— CH2— NH3CI 



Hydrochloride of a-Aminocam- 

 pholic Acid. (a)D = 44.7°. 



CH.— C ( CH. ) — CH0NH2 



C(CH3), 



I 

 CH,— CH— CO„H 



^-Aminocampholic Acid. 

 (a)D= 16.4°. 



CH3— C ( CH3) — CH.NH.Cl 



C(CH3)3 

 CH,— CH— CO„H 



Hydrochloride of |8-Aminocam- 

 pholicAcid. (a)D=:4i.3°. 



CH2— C(CH3)NH2 



C(CH3), 



CH,— CHCO^Na 



Sodium Salt of Aminodihydro- 



campholytic Acid. 



(a)z, = i8.3°. 



CH^— C(CH3)CO 



C(CH3), 



\ 



CH.— CH- 



-CH, 



/ 



NH 



Anhydride of a-Aminocampholic 

 Acid. (a)D— — 33-9°- 



CH.— C(CH3)— CO.Na 



C(CH3), 



CH3— CN— CH2— NH2 

 Sodium Salt of a-Aminocam- 

 pholic Acid, (a) D = 62.4°. 



CH,— C(CH3)— CH. 



C C(CH3), 

 CH.,— CH 



CO 





NH 



Anhydride of /3-Aminocampholic 

 Acid. (a)z) = 66.5°. 



CH,— C(CH3)CHoNH2 



C(CH3), 



I 



CH,— CH— CO.Na 

 Sodium Salt of /3-Aminocam- 

 pholic Acid. (a)D = H-3°- 



It will be noticed that the aminocamphonanic acid and amino- 

 dihydrocampholytic acid are represented as having a cyclic or inner 

 salt structure, w'hile the aminocampholic acids are both represented 

 as having an open structure. The evidence for these structures is 

 based on the specific rotations of the compounds. The rotation of 

 the sodium salt and hydrochloride of aminocamphonanic acid are to 

 the right while that of the anhydride, which is undoubtedly cyclic in 



