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Four Hydrogen Bonds − DDAA, DADA, DAAD and ADDA Hydrogen Bond Motifs
Author(s) -
Lüning Ulrich,
Kühl Christine,
Uphoff Andreas
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<4063::aid-ejoc4063>3.0.co;2-l
Subject(s) - chemistry , hydrogen bond , substituent , covalent bond , aminopyridines , chloroform , molecule , selectivity , stereochemistry , acceptor , proton nmr , crystallography , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , physics , condensed matter physics
Abstract Receptor molecules containing four hydrogen‐bond acceptor or donor sites based on aminopyridines, aminonaphthyridines and urea subunits have been synthesized and their association has been investigated. DDAA ( 13a − c ) and DADA ( 18a − b ) arrays may form homodimers, while DAAD ( 24a − d ) with ADDA ( 25a − b ) may form heterodimers. While most parent heterocycles were only slightly soluble in standard organic solvents, substitution was able to enhance the solubility in most cases. The naphthyridine 24d , bearing a substituent derived from lysine, possesses potential anchor groups for a covalent connection. Binding studies were carried out in chloroform and monitored by 1 H NMR, and the binding constants K ass for the heterodimers DAAD·ADDA ( 24·25 ) were compared to the binding of smaller (ADD, 26 ) or mismatching (DADD, 27 ) counterparts, showing that the matching heterodimer is formed with a selectivity of > 50. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)