The influence of cation-π and anion-π interactions on the strength and nature of N⋯H hydrogen bond

► The continuum of N⋯H interactions ranging from weak to medium hydrogen bonds is observed. ► With regard to ion type, proper and improper hydrogen bonds have been observed. ► The order of E2 of LpN→σHF∗ interaction may be connected with hybridization of LpN. ► Unlike dN⋯H, ρN⋯H and E2 decrease/increase in the presence of cation-π/anion-π. ► The nucleophilicity of s-triazine is diminished/amplified by cations/anions.