The instantaneous hydrogen-deuterium exchange (H/D exchange) is mostly applied to exchangeable protons and deuteriums such as those in hydroxyl or amine groups. Therefore, this quick H/D exchange of the hydrogens on the carbon in aromatic compounds has not been reported even with a metal catalyst to my knowledge. However, the unexpected pH-dependent aromatic H/D exchange in 1,8-diamino-2,7-naphthyridine-4-carbonitrile systems has been observed in NMR analysis immediately after adding D<sub>2</sub>O. 1,8-diamino-3,6-bis(1-pyrrolidinyl)-2-7-naphthyridine-4-carbonitrile and 1,8-diamino-3,6-bis(N-methylpiperazine)-2-7-naphthyridine-4-carbonitrile have been synthesized and characterized exhibiting unusual chemical properties. Both free and protonated forms of the compounds were studied by quantum calculation and experiments including NMR titrations and pH titrations by various methods. The outcomes showed that the protonation alters the structure and reactivity of the compounds.

Study of pH-dependent H/D exchange from aromatic hydrogen in 1,8-diamino-2,7-naphthyridine-4-carbonitriles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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