The gas-phase reactivity of selected ionic species with borazine and of borazine-derived ions with selected neutrals has been studied by FT-ICR and ab initio computations and related to the corresponding ion chemistry of benzene. The most basic site of borazine is at nitrogen, and its conjugate acid, H 3 B 3 N 3 H 4 + , is similar in structure to the benzenium ion, as shown by ab initio calculations. H 3 B 3 N 3 H 4 + ions undergo H/D exchange of up to four hydrogens with CD 3 OD and do not isomerize by stepwise 1,2-hydrogen shifts. Protonation at boron is calculated to be unfavored by 28 kcal/mol with respect to protonation at nitrogen. The H 4 B 3 N 3 H 3 + ions show the features of a [B 3 N 3 H 5 ‚‚‚H 2 ] + complex, prone to dissociation at room temperature. The experimental gas-phase basicity of borazine is equal to 185.0 ( 1 kcal/mol. The Lewis basicity toward Me 3 Si + places borazine into a linear correlation pertaining to model aromatic compounds. The experimental gas-phase acidity is 365.4 ( 1.5 kcal/mol. The reactions of neutral borazine with protonating, alkylating, and nitrating ions have been characterized and compared with the corresponding reactions of benzene. B 3 N 3 H 5 + ions, retaining a cyclic structure, react similarly, in some respects, as phenylium ions, C 6 H 5 + .