Tautomeric Self-Dimerization and Molecular Recognition Properties of2-Aminopyrimidinone Derivatives as Triple Hydrogen-Bonding Modules in Molecular Assemblies
✍ Scribed by Hajime Abe; Masayoshi Takase; Yasuhiro Doi; Shinya Matsumoto; Masaru Furusyo; Masahiko Inouye
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 200 KB
- Volume
- 2005
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
A triple hydrogen‐bonding module based on 6‐alkynyl‐2‐amino‐3__H__‐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 (Δ__G__~298~ = –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 (Δ__G__~298~ = –31 kJ/mol) is one of the highest values among triple hydrogen‐bonded complexes so far reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)