A proton magnetic resonance study of the aminotetrazole–iminotetrazoline tautomerism of some substituted methylaminotetrazoles

Abstract

A direct detection of the aminotetrazole–iminotetrazoline tautomerism for 1-methyl-5-methylaminotetrazole and 1-p-tolylideneamino-5-methylaminotetrazole was obtained from the H n.m.r. spectra of these materials in deuteriodimethyl sulphoxide solution. Addition of water altered the tautomerism in favour of the amino-form. Hydrogen bonding between the tetrazole molecules and the solvent was detected in the solutions of 1-methyl-5-methylaminotetrazole.