865366-49-0Relevant academic research and scientific papers
Tautomeric self-dimerization and molecular recognition properties of 2-aminopyrimidinone derivatives as triple hydrogen-bonding modules in molecular assemblies
Abe, Hajime,Takase, Masayoshi,Doi, Yasuhiro,Matsumoto, Shinya,Furusyo, Masaru,Inouye, Masahiko
, p. 2931 - 2940 (2005)
A triple hydrogen-bonding module based on 6-alkynyl-2-amino-3H-pyrimidin-4- one was developed such as for self-dimerization and for nucleobase recognition processes. The strength of the module for the self-dimerization was determined by NMR and fluorimetric analyses in chloroform (ΔG298 = -22 to -23 kJ/mol). DFT calculations and X-ray structure analysis showed that the self-dimerization consists of the three-point hydrogen-bonding including two kinds of tautomers of the module in an ADD·DAA mode. Selective recognition of the module for a cytidine derivative was also observed, and the free energy change for the complexation (ΔG298 = -31 kJ/mol) is one of the highest values among triple hydrogen-bonded complexes so far reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
