Quilibrium constants, K, have been determined for the reduction of 10-methylacridinium ion by 15 N-heterocyclic hydride donors: acridine, quinoline, pyridine, and phenanthridine derivatives. The solvent was a mixture of 2-propanol and water in the ratio 4:l by volume. Reduction potentials have been estimated for the corresponding cations in aqueous solution by assuming that the ICs would be the same and accepting -361 mV as the reduction potential of the 3-(aminocarbonyl)-l-benzylpyridinium ion. These reduction potentials span 430 mV. Values of pKR have also been determined for six of the cations in the same solvent. For derivatives of the same ring system, -A log K is approximately equal to ApK,, but a 4 log unit discrepancy appears when phenanthridine derivatives are compared with the 9-methylacridinium ion.Nitration studies have been conducted on the bis(acetamido), bis(p-toluenesulfonamido), and bis(trifluor0acetamido) derivatives of 2,6-diamino-4,8-dinitroand 1,5-diaminonaphthalene. The bis(trifluor0acetamides) were nitrated readily to produce tetranitro derivatives, whereas the p-toluenesulfonamides and acetamides gave predominantely dinitro products. The tetrakis(trifluoroacety1) and tetraacetyl derivatives of 1,3,5,7-tetraaminonaphthalene were nitrated to yield di-and mononitro products, respectively. Solvolysis of some of the amides was successful (most facile with trifluoroacetamido), leading to the first preparations of 2,6-diamino-1,4,5,8-tetranitro-, 1,5-diamino-4,8-dinitro-, and 1,5-dinitro-2,4,6,8-tetraaminonaphthalenes. Peracid oxidation of the new diamines or amides failed to yield polynitronaphtlalenes. The effect of structure on the course of nitration, solvolysis, and oxidation of the new nitrated naphthalene derivatives is discussed.