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- W2127393075 endingPage "1693" @default.
- W2127393075 startingPage "1682" @default.
- W2127393075 abstract "1,8-Bis(tetramethylguanidino)naphthalene (TMGN, 1) is a new, readily accessible, and stable proton sponge with an experimental pK(BH(+)) value of 25.1 in MeCN, which is nearly seven orders of magnitude higher in basicity than the classical proton sponge 1,8-bis(dimethylamino)-naphthalene (DMAN). Because of the sterically less crowded character of the proton-accepting sp(2)-nitrogen atoms, TMGN also has a higher kinetic basicity than DMAN, which is shown by time-resolved proton self-exchange reactions. TMGN is more resistant to hydrolysis and is a weaker nucleophile towards the alkylating agent EtI in comparison to the commercially available guanidine 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD). Crystal structures of the free base, of the mono- and bisprotonated base were determined. The dynamic behavior of all three species in solution was investigated by variable-temperature (1)H NMR experiments. DeltaG (++) values obtained by spectra simulation reveal a concerted mechanism of rotation about the C-N bonds of the protonated forms of TMGN." @default.
- W2127393075 created "2016-06-24" @default.
- W2127393075 creator A5009427578 @default.
- W2127393075 creator A5014033749 @default.
- W2127393075 creator A5043862650 @default.
- W2127393075 creator A5045155782 @default.
- W2127393075 date "2002-04-02" @default.
- W2127393075 modified "2023-10-13" @default.
- W2127393075 title "1,8-Bis(tetramethylguanidino)naphthalene (TMGN): A New, Superbasic and Kinetically Active “Proton Sponge”" @default.
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