The first rhena-analogues of pyridinium (cyclopropametalla-2-isoquinolinium complexes) are obtained from o -ethynyl benzonitriles. Structural analysis and DFT calculations confirm their aromatic nature. Compared to rhenapyrylium, rhenapyridinium has a slightly stronger Hückel π-aromaticity, while a chlorine substituent on the rhenapyridinium ring decreases its aromaticity, which is revealed by NICS, EDDB, MCI and ΔBV(ELF π ) analysis.