A regioselective sythesis of 2-nitro-meso- tetraarylporphyrinato metal was achieved by reaction of mesotetraarylporphyrinato metal with relative metal nitrate salt in acetic acid/acetic anhydride. The yield of 2-nitro substituted porphyrin depended on the coordinated metal. When the metal was Cu(Ⅱ) or Ni(Ⅱ), quantitative yields of 2- NO2-5, 10, 15, 20-tetra(4-methoxyphenyl) porphyrinato Cu(Ⅱ) and Ni(Ⅱ) were obtained in 5 min and 50 min, respectively, at 45℃, while the metals are Co(Ⅱ) and Zn(Ⅱ), 64% and 12% of 2-NO2-5, 10, 15, 20- tetra(4-methoxyphenyl) porphyrinato metal were obtained in 100 min and 120 min, respectively. The same metal effects were also found with other meso-substituted porphyrins. Electron-donating substituents accelerated the reaction and electron-withdrawing substituents had the opposite effect. The effects of complexed metal ions and meso- substituents are discussed.

Key words: REGIOSELECTIVITY, STEREOSELECTIVITY, METAL ION, SUBSTITUENT EFFECT, NITRATE, PORPHYRIN, METAL COMPLEX