1. Controlling Keto-Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array
- Author
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Zengming Fan, Shuaiwei Qi, Qinwen Ding, Chenyang Zhang, Shizhong Mao, Jing Zhang, and Zeyuan Dong
- Subjects
chemistry.chemical_classification ,Ketone ,Chemistry ,Hydrogen bond ,Dimer ,Organic Chemistry ,Intermolecular force ,Supramolecular chemistry ,Keto–enol tautomerism ,Biochemistry ,Tautomer ,Supramolecular assembly ,Crystallography ,chemistry.chemical_compound ,Physical and Theoretical Chemistry - Abstract
Units of ureidopyrimidinone (UPy) which dimerize via strong quadruple hydrogen bonding are widely used for the construction of supramolecular systems. This self-complementary system exists in the tautomerism equilibrium of 4[1H]-pyrimidinone dimer and pyrimidin-4-ol dimer, making generated supramolecular assembly systems essentially complicated. In this contribution, a rational but simple design concept is described for preorganizing the self-complementary quadruple hydrogen bonding of UPy via supramolecular strategy into a single-quadruple DDAA-AADD dimeric array. With this concept, the designed UPy derivatives form only 4[1H]-pyrimidinone dimer with a ketone configuration via intermolecular hydrogen-bonding interactions, both in the solid state as well as in solution, as is evident from single-crystal X-ray diffraction and 1H NMR spectroscopy. The single DDAA-AADD dimeric array provides defined noncovalent driving forces that can be used to generate constitutionally clear supramolecular structures that are vitally important in the fields of supramolecular chemistry and materials.
- Published
- 2020