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Continuing our work on hydrazyl free radicals, five triphenylhydrazine derivatives, one a new compound, were synthesized to compare the electronic and molecular properties of these compounds, study the influence of substituents on the phenyl rings, and compare their properties with the parent hydrazines and corresponding anions. These hydrazines demonstrate both acid-base and redox properties. The hydrazine proton can be removed by base, yielding the corresponding anion and both the hydrazines and their anions can be oxidized to the corresponding hydrazyl free radicals. ESR spectra confirmed their formation and X-ray crystallography of one compound confirmed their structures. N H N NO2 O2N N H N N NO2 O2N N H N NO2 O2N NH N N H N NO2 O2N O2N N H N NO2 O2N O2N N H N

Synthesis and spectral comparison of electronic and molecular properties of some hydrazines and hydrazyl free radicals