Solution

ID: past-exam-of-the-mphil-in-micro-and-nanotechnology-enterprise-course-of-the-university-of-cambridge/2021/paper-1/10/ii/b/solution

The terminal ureidopyrimidinone groups supply the association sites. Their urea/pyrimidinone NH donors and carbonyl/ring-nitrogen acceptors can form a self-complementary array of four hydrogen bonds between two UPy units. Joining the two terminal units of one molecule by this noncovalent association closes the ring.
The ether-containing arms provide flexibility and spacing; they are not covalently joined together during ring formation. The ring is therefore a supramolecular conformation of the existing molecule, rather than a new covalent ether macrocycle.

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