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Novel multiply hydrogen-bonded heterodimers based on heterocyclic ureas. Folding and stability
- Source :
-
Tetrahedron . Feb2004, Vol. 60 Issue 9, p2063. 7p. - Publication Year :
- 2004
-
Abstract
- A new series of multiply hydrogen-bonded heterodimers have been self-assembled in chloroform-d, with ureidopyrimidone derivatives 2 and 3 and 2,7-diamino-1,6-naphthyridine diamide 4 and ureas 5 and 6 as monomers. The self-associating behavior of the compounds and the binding modules of the new heterodimers have been investigated. New tri-center hydrogen bonds have been proposed to explain the stability of the new heterodimers. 2D-NOESY, COSY and temperature variable 1H NMR studies revealed that all the new heterodimers are substantially more stable than the ureidopyrimidone-based quadruply hydrogen-bonded homodimers in chloroform-d. As a result, heterodimers 2·4 and 3·4 were assembled quantitatively, while heterodimers 2·5, 3·5, 2·6, and 3·6 were formed in 80–85% yields. It is also revealed that intramolecular hydrogen bonds formed in monomers 5 and 6 reduce the stability of the corresponding heterodimers. [Copyright &y& Elsevier]
- Subjects :
- *HYDROGEN bonding
*DIMERS
*HETEROCYCLIC compounds
*CHLOROFORM
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 60
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 12171780
- Full Text :
- https://doi.org/10.1016/j.tet.2003.12.063