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The strongly basic 1,8-bis(tetramethylguanidino)naphthalene (TMGN) has been mono- and di-protonated by pentachlorophenol (PCP) and HClO 4 acid. Formation of hydrogen bonds in the 1:1 and 1:2 mixtures in acetonitrile has been studied by FT-IR, 1 H NMR; 13 C NMR spectroscopy as well as in the gas phase by ESI MS and PM5 semiempirical methods. The spectroscopic data show that...
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