Synthesis and spectrophotometry study of the acid-base properties of nitro-substituted 5-phenyl-β-octaalkylporphines

Abstract

10,15-Dinitro-5-phenyl-2,3,7,8,12,13,17,18-octamethylporphine, 10,15,20-trinitro-5-phenyl-2,3,7,8,12,13,17,18-octamethylporphine, and 10,15,20-trinitro-5-(4-nitrophenyl)-2,3,7,8,12,13,17,18-octamethylporphine were synthesized and identified by electronic absorption, IR, and ¹Н NMR spectroscopy. The acid–base properties of the synthesized compounds were studied by spectrophotometric titration in HClO₄–acetonitrile and 1,8-diazabicyclo[5.4.0]undec-7-ene–acetonitrile systems at 298 K. Parameters of the electronic absorption spectra and concentration ranges of existence of the mono- and diprotonated, as well as mono- and dideprotonated forms of the corresponding ligands and the acid and base dissociation constants of the latter were determined. Comparative analysis of the effect of nitro groups on the reactivity of the synthesized compounds was performed.