Proton transfer reactions from dimethyl (4-nitrophenyl)malonate to N-bases in acetonitrile

Add time:07/21/2019    Source:sciencedirect.com

Deprotonations of dimethyl (4-nitrophenyl)malonate (C-acid) by 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and 1,8-bis(dimethylamino)naphthalene (DMAN) in acetonitrile were studied by kinetic as well as FTIR and 1H NMR spectroscopic methods. In the 1:1 mixture of C-acid with DMAN no proton transfer was found. The N-bases with guanidine-like character deprotonate C-acid in the acetonitrile solution quantitatively. The mechanisms of proton transfer reactions are discussed.

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