American Chemical Society
ol016750a_si_003.cif (50.54 kB)

A Multiple Hydrogen-Bond Scaffold Based on Dipyrimidin-2-ylamine

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posted on 2001-11-09, 00:00 authored by Serge H. M Söntjens, Joris T. Meijer, Huub Kooijman, Anthony L. Spek, Marcel H. P. van Genderen, Rint P. Sijbesma, E. W. Meijer
A multiple hydrogen-bond array based on dipyrimidin-2-ylamine is presented, which is easily accessible. The influence of a preorganizing intramolecular hydrogen bond, tautomeric equilibria, and steric effects on the association behavior were investigated. X-ray diffraction shows that the molecules feature an ADA (acceptor−donor−acceptor) array of hydrogen-bonding sites in the solid state. The array persists in solution, and 1H NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.