A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine

S.H.M. Sontjens, J.T. Meijer, H. Kooijman, A.L. Spek, M.H.P. Genderen, van, R.P. Sijbesma, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

24 Citations (Scopus)

Abstract

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 H-1 NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound.
Original languageEnglish
Pages (from-to)3887-3889
JournalOrganic Letters
Volume3
Issue number24
DOIs
Publication statusPublished - 2001

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