Alkyl substitution on the amino nitrogen, vinylogy (but not benzology)
, iminology, and alkyl substitution on the functional carbon of the am
idine skeleton in cyanamide iminologues increase the hydrogen-bonding
basicity of cyanamide and produce, on the pK(HB) scale, super-basic ni
triles more basic than tertiary amines. On the gas-phase basicity scal
e iminology also increases the basicity of cyanamide, but sp-nitrogen
bases remain less basic than sp2- or sp3-nitrogen bases.