The preparation of several 1-allcy 1-5-nitraminoand 5-alkyl-nitraminotetrazoles is described. Comparison of the apparent dissociation constants and ultraviolet absorption spectra of these compounds and of 5-nitraminotetrazole indicates that the strong first dissociation of the latter is associated with the hydrogen of the nitramino group.Recently 5-nitraminotetrazole was characterized as a dibasic acid with pK values of 2.5 and 6. 1.3
The similarity between 5-aminotetrazole and guanidine in certain structural features suggested that nitraminotetrazole might be prepared from 5-aminotetrazole much as nitroguanidine can be prepared from guanidine. 5-Aminotetrazole has generally been looked upon as an acidic substance since it was first described by Thiele (1). Although the amino group can be acylated (2) and under suitable conditions diazotized (1), its salts with mineral acids are extensively hydrolyzed in aqueous solution.5-Aminotetrazole nitrate (3) can be prepared by crystallization of 5-aminotetrazole from warm, moderately concentrated nitric acid. Presumably the amino group is involved in salt formation, although participation of the ring nitrogens cannot be excluded. Dehydration of the nitrate with sulfuric acid at room temperature led \ j|.he formation of a nitraminotetrazole. Analogy with the guanidine series suggested that 5-nitroaminotetrazole (I) would be formed but structures such as l-nitro-5-aminotetrazole (II) or 2-nitro-5-aminotetrazole
Students are given a problem in which they are to determine which of two published accounts of reaction products involving derivatives of idene is correct.
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