A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine.
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]
Söntjens
S H
SH
Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
Meijer
J T
JT
Kooijman
H
H
Spek
A L
AL
van Genderen
M H
MH
Sijbesma
R P
RP
Meijer
E W
EW