Three hydrogen bonds are formed between creatinine and derivatives of
2-amino-4(3H)pyrimidone. Changes in the tautomer ratio of the latter u
pon complexation can be observed by UV spectroscopy. The formation of
a further hydrogen bond between creatinine and a 4-aminoacridin-5-yl-a
mino-substituted 4(3H)pyrimidone seems to be sterically prevented. The
properties of three other, quite different compounds assumed to form
three hydrogen bonds with creatinine have also been investigated. Dode
cyl 4-octadecylallophanate and 2,6-bis(dodecylamino)-pyridine do not a
ssociate appreciably with creatinine, which can be explained by the fo
rmation of an intramolecular hydrogen bond in the former compound and
the lack of tautomerization of the latter. With 6-(1-heptyloctylamino)
-2(1H)-pyridone, however, creatinine forms a complex that is almost as
stable as those with 2-amino-4(3H)-pyrimidone derivatives.