Extremely strong but sluggish amine bases

Abstract
1,8-Bis(dimethylamino)-(3) and 1,8-bis(diethylamino)-2,7-dimethoxynaphthalene (4) are extremely strong bases with pKa > ca. 16, but proton transfers to and from these amines are exceptionally slow; the reaction involving the protonated form of (4) and hydroxide ion in 60% Me2SO–H2O (v/v) can be followed with a conventional spectrophotometer (tfrac12;ca. 15 s).