A. Coker et F. Hibbert, SUBSTITUENT EFFECTS LEADING TO ULTRA-SLOW PROTON REMOVAL FROM AN INTRAMOLECULAR HYDROGEN-BOND, Perkin transactions. 2, (1), 1995, pp. 1-2
Electron-withdrawing substituents (R(2) and R(3)) result in a remarkab
le reduction in the rate coefficient for removal of the hydrogen-bonde
d proton, from 2-alkyl-4-(R(2), R(3)-phenylazo) resorcinol monoanions
by hydroxide ion such that the reaction can be followed by conventiona
l spectrophotometry with t(1/2) in the range of minutes.