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

[GRAPHICS] 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...

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Bibliographic Details
Published in:Organic letters Vol. 3; no. 24; pp. 3887 - 3889
Main Authors: Sontjens, SHM, Meijer, JT, Kooijman, H, Spek, AL, van Genderen, MHP, Sijbesma, RP, Meijer, EW
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 29.11.2001
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISSN:1523-7060, 1523-7052
Online Access:Get more information
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Summary:[GRAPHICS] 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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol016750a