Organo-peroxyl compounds via catalytic oxidation of a hindered phenol and aniline utilizing new manganese(II) bis benzimidazole diamide based complexes

Bis benzimidazole diamide ligand-N,N′-bis(2-methylbenzimidazolyl) propanediamide [GBMA = L] has been synthesized and utilized to prepare new Mn(II) complexes of general composition [Mn(L)X2]·nH2O where X is an exogenous anionic ligand(X = Cl−, CH3COO−, SCN−). The geometry of the ligand and its Mn(II) complex have been optimized at the level of UHF, by using ZINDO/1 method. Binding energies, heat of formation and bond lengths of geometry optimized structures for the ligand and complex have been obtained. The oxidation of 2,4,6-tri-tert.-butylphenol (TTBP) and 2,4,6-tri-tert.-butylaniline (TTBA) has been investigated using these Mn(II) complexes as catalyst and TBHP as an alternate source of oxygen. The organo-peroxyl compounds have been isolated and characterized by 1H NMR, 13C NMR, IR and mass data. A different product profile was obtained when H2O2 is used as an oxidant.

Graphical abstractBis benzimidazole diamide ligand-N,N′-bis(2-methylbenzimidazoyl)-propanediamide [GBMA] has been synthesized and utilized to prepare new Mn(II) complexes. The oxidation of 2,4,6-tri-tert.-butylphenol (TTBP) and 2,4,6-tri-tert.-butylaniline (TTBA) using Mn(GBMA)Cl2 complex as catalyst and TBHP as an alternate source of oxygen results in organo-peroxyl compounds which has been characterized by 1H NMR, 13C NMR, UV–Vis, IR and mass data. A different product profile was obtained when H2O2 is used as an oxidant..Figure optionsDownload full-size imageDownload as PowerPoint slide