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

S H Söntjens; J T Meijer; H Kooijman; A L Spek; M H van Genderen; R P Sijbesma; E W Meijer

doi:10.1021/ol016750a

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

Org Lett. 2001 Nov 29;3(24):3887-9. doi: 10.1021/ol016750a.

Authors

S H Söntjens¹, J T Meijer, H Kooijman, A L Spek, M H van Genderen, R P Sijbesma, E W Meijer

Affiliation

¹ Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.

PMID: 11720561
DOI: 10.1021/ol016750a

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 (1)H NMR titrations show that molecules with sterically nondemanding DAD arrays are selectively bound. [structure: see text]