Four hydrogen bonds - DDAA, DADA, DAAD and ADDA hydrogen bond motifs

European Journal of Organic Chemistry

Volumn , Issue 23, 2002, Pages 4063-4070

  Lüning, Ulrich ^a   Kühl, Christine ^b   Uphoff, Andreas ^a  

^a UNIVERSITY OF KIEL   (Germany)

^b Bernina Biosystems   (Germany)

Author keywords

Association constants; Heterocycles; Hydrogen bond; Molecular recognition; Supramolecular chemistry

Indexed keywords

AMINOPYRIDINE; HETEROCYCLIC COMPOUND; UREA DERIVATIVE;

ARTICLE; BINDING AFFINITY; COVALENT BOND; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SUPRAMOLECULAR CHEMISTRY; TITRIMETRY; X RAY ANALYSIS;

EID: 0036898419     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200212)2002:23<4063::AID-EJOC4063>3.0.CO;2-L     Document Type: Article

References (36)

1. L. Stryer, Biochemistry, W. H. Freeman and Company, New York, 1995.
2. When several hydrogen bonds are positioned next to each other, the hydrogen bond donor and acceptor sites may be located on the same or on opposite sides (e.g., DD·AA versus DA·DA). We use the expressions parallel and anti-parallel, respectively. In a parallel orientation, additional attractive secondary interactions exist, while the secondary interactions in an anti-parallel orientation are repulsive; see also ref.[4]
3. See ref.[1], part V.
4. This rule has exceptions. According to investigations by Schneider et al., [5] each hydrogen bond contributes approx. 8 kJ/mol to the binding enthalpy. However, when hydrogen bonds are oriented next to each other, secondary Coulomb interactions[6.7] either favour or disfavour binding. Two parallel bonds additionally contribute approx. 3 kJ/mol while anti-parallel hydrogen bonds reduce the binding enthalpy by approx. 3 kJ/mol, due to electrostatic repulsions.
5. J. Sartorius, H.-J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452.
6. W. L. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2008-2010.
7. S. C. Zimmerman, P. S. Corbin, Struct. Bonding 2000, 96, 63-94.
8. F. H. Beijer, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Meijer, Angew. Chem. 1998, 110, 79-82; Angew. Chem. Int. Ed. 1998, 37, 75-78.
9. F. H. Beijer, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Meijer, Angew. Chem. 1998, 110, 79-82; Angew. Chem. Int. Ed. 1998, 37, 75-78.
10. F. H. Beijer, R. P. Sijbesma, H. Kooijman, A. L. Spek, E. W. Meijer, J. Am. Chem. Soc. 1998, 120, 6761-6769.
11. B. J. B. Folmer, R. P. Sijbesma, E. W. Meijer, J. Am. Chem. Soc. 2001, 123, 2093-2094, and refs. cited.
12. Further DDAA systems have been described, but tautomerization may occur, altering the DDAA sequence into a DADA: P. S. Corbin, S. C. Zimmerman, J. Am. Chem. Soc. 1998, 120, 9710-9711.
13. R. P. Sijbesma, F. H. Beijer, L. Brunsveld, B. J. B. Folmer, J. H. K. K. Hirschberg, R. F. M. Lange, J. K. L. Lowe, E. W. Meijer, Science 1997, 278, 1601-1604.
14. L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097.
15. DDAA and DADA arrays with a larger distance between the four hydrogen bonds have also been reported: B. Gong, Y. Yan, H. Zeng, E. Skrzypczak-Jankunn, Y. W. Kim, J. Zhu, H. Ickes, J. Am. Chem. Soc. 1999, 121, 5607-5608.
16. D. K. J. Gorecki, E. M. Hawes, J. Med. Chem. 1977, 20, 838-841.
17. Related DDAA and DAAD sequences have been investigated recently by: P. S. Corbin, S. C. Zimmerman, P. A. Thiessen, N. A. Hawryluk, T. J. Murray, J. Am. Chem. Soc. 2001, 123, 10475-10488.
18. U. Lüning, C. Kühl, M. Bolte, Acta Crystallogr., Sect. C 2001, 57, 989-990.
19. M. Bolte, C. Kühl, U. Lüning, Acta Crystallogr., Sect. E 2001, 57, 502-504.
20. S. C. Zimmerman, P. S. Corbin, J. Am. Chem. Soc. 2000, 122, 3779-3780.
21. J. J. Baldwin, A. W. Raab, G. S. Ponticello, J. Am. Chem. Soc. 1978, 100, 2529-2535.
22. Meijer's DDAA unit may equilibrate to a tautomeric DADA unit, see ref.[9]
23. P. E. Nielsen, M. Egholm, R. H. Berg, O. Buchardt, Science 1991, 254, 1497-1500.
24. Peptide Nucleic Acids: Protocols and Applications (Eds.: P. E. Nielsen, M. Egholm), Horizon Scientific Press, Oxford, 1999
25. U. Diederichsen, H. W. Schmitt, Angew. Chem. 1998, 110, 312-315; Angew. Chem. Int. Ed. 1998, 37, 302-305 and refs. cited.
26. U. Diederichsen, H. W. Schmitt, Angew. Chem. 1998, 110, 312-315; Angew. Chem. Int. Ed. 1998, 37, 302-305 and refs. cited.
27. E. E. Fenlon, T. J. Murray, M. H. Baloga, S. C. Zimmerman, J. Org. Chem. 1993, 58, 6625-6628.
28. U. Lüning, C. Kühl, Tetrahedron Lett. 1998, 39, 5735-5738.
29. Ethyl pyridin-2-ylcarbamate and ethyl 6-methylpyridin-2-ylcarbamate: A. R. Katritzky, J. Chem. Soc. 1956, 2063-2064.
30. Beilsteins Handbuch der Organischen Chemie, 4th Ed., 3rd and 4th Ergänzungswerk, vol. 22, Springer Verlag, Berlin, 1979, p. 3896.
31. N,N′-Bis(6-methyl-2-pyridyl)urea: G. R. Clemo, B. W. Fox, R. Raper, J. Chem. Soc. 1954, 2693-2701.
32. Corbin, Zimmerman et al. have carried out more detailed experiments for closely related systems, to prove the four hydrogen bonds; see ref.[27]
33. max being the parameters to be fitted.
34. The related compounds 26 (ADD) and 27 (DADD) have been synthesized by addition of 2-aminopyridine or 2,6-diaminopyridine, respectively, to butyl isocyanate. For 26 see: G. Crosby, F. Niemann, J. Am. Chem. Soc. 1954, 76, 4458-4462.
35. S. Brammer, U. Lüning, C. Kühl, Eur. J. Org. Chem. 2002, 4054-4062.
36. In this case, the estimation of ref.[15] fits well, but see ref.[7]