The reaction 1-(1-hydroxybenzotriazolyl)-2,4-dinitrobenzene 1 and 2-(1-hydroxybenzotriazolyl)-5-nitro-pyridine 2 with amines undergoes amination followed by elimination of the 1-hydroxyl benzotriazolyl anion. The kinetic data for the reaction of 1 and 2 with Mo, CHA and An in MeOH and AN proceeded by uncatalysed mechanism in which the rate limiting step is the leaving group departure, whereas the reaction with Mo in toluene proceeded by uncatalysed mechanism in which the formation of the zwitterionic intermediate is the rate determining step. While the reactions of 1 with CHA and An and the reaction of 2 with CHA in toluene proceeded by SB mechanism in which the rate determining step is the proton transfer process. The reactions of 1 and 2 with Mo in the three solvents and with CHA and An in MeOH and AN is greatly depended on the stability of the zwitterionic intermediate. The effect of ring activation is due to the ground state stabilization and the more efficient delocalization of the negative charge with a nitro group than with a ring-nitrogen in the transition state. The low activation enthalpies ΔH # and the highly negative activation entropies ΔS # are due to the intramolecular hydrogen bonding with the ammonio hydrogen present in the transition state.

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The rates of reaction of a series of substituted naphthoxides with 1‐chloro‐2,4‐dinitrobenzene in methanol, and the pKa values of the naphthols in 50% methanol have been measured. A linear free energy relationship applies well to these reactions. The rate constants are correlated with the pKa values of the corresponding naphthols via the Brönsted equation giving a β values of 0.94. A linear correlation between ΔH‡ and ΔS‡ is indicative of single mechanism. The nmr spectra of the substituted naphthols have been measured in DMSO·d6.

Two hydrogen bonded complexes between 1,8- bis(dimethylamino) naphthalene (DMAN) and 2,6-dihydroxynaphthalene (DHN) in 2:1 and 1:2 ratios were synthesised and studied using FTIR the spectra of the solid 2:1 complex revealed incomplete protonation of DMAN with the appearance of two broad absorptions representing ν(NHN)+ and ν(OHN) in the ranges 700–400 and 1600–700 cm−1 respectively, while the 1:2 complex indicated the complete protonation of DMAN with the appearance of two broad absorptions representing ν(NHN)+ and ν(OHO-) in the ranges 700–400 and 1600–700 cm−1 respectively. On the other hand the IR spectra in acetonitrile indicated that the 1:2 complex is more stable than the 2:1 complex.