Characterization of 3-Aminophenazin-2-ol Isolated from the Chemical Oxidation of o-Phenylenediamine

Self-assembled centimetre-sized rods obtained in the oxidation of o -phenylenediamine and aniline

“…However, based on the results of elemental analyses and MS data, we propose a mixture of 2,3‐phenazinediamine and 3‐aminophenazin‐2‐ol ( α and β in Scheme ). This is in line with the report by Iseminger et al , where they were able to separate the two products.…”

“…These values for (a) are very close to those for the following solvated forms of the proposed products α and β (Scheme ), 30% α ·HCl·2H 2 O + 70% β ·HCl·2H 2 O, as reported by Iseminger et al (%): C, 49.45; H, 4.63; N, 15.50; Cl, 13.54; S, N/A.…”

“…In the 13 C NMR spectra of rods prepared with 30 mmol L −1 o PD without aniline and with 50 mmol L −1 aniline, signals were observed (in ppm) at ca {91.35, 96.37, 106.16, (C‐4), α + β }, {118.26, 122.44, 127.24, 128.07, 128.51, 128.62, 131.58, 132.12, 133.94, (C‐5, 6, 7, 8), α + β }, {136.98, 138.72, (C‐10, 11), α + β }, {144.78, C‐3( α )}, {149.05, C‐3( β )}, {153.20, 154.49, C‐2( β )}. The large number of peaks in each 13 C NMR spectrum (18) is consistent with the products being a mixture of two dimers as suggested by Iseminger et al , or an open trimer with lower symmetry …”

“…Partial hydrolysis of produces , and the ratio of / decreases with an increase of acid strength. It is interesting to note that the results for the elemental analysis of the samples prepared with 0.37 mol L −1 HCl are very similar to those reported by Iseminger et al 21 even though they used 1 mol L −1 HCl.…”

“…Proton spectra with similar features have previously been assigned to the open trimer structure. 24 In the 13 (18) is consistent with the products being a mixture of two dimers as suggested by Iseminger et al, 21 or an open trimer with lower symmetry. 24 NMR investigations of mixtures can be very challenging.…”