(Solved):   1. Cucurbiturils are macrocyclic molecules made of glycouril monomers linked by methylene ...

 

1. Cucurbiturils are macrocyclic molecules made of glycouril monomers linked by methylene bridges. The accepted shorthand is \( C B(n) \) where \( n \) is the number of glycouril units in the ring. (a) Give a general synthetic route to form \( \mathrm{CB}(6) \) and explain how this route can be altered to generate other size rings. (4 Marks) \( \mathrm{CB}(7) \) is known to bind many different guests with high affinity. Molecules \( \mathbf{A} \), B, C and \( \mathbf{D} \), pictured below have been measured and their binding constant, in water, are given in the table below. (b) Explain the trend in binding constants observed in the table above. (4 Marks) (c) Using diagrams, depict the possible types of non-covalent interaction between \( \mathrm{CB}(7) \) and molecules \( \mathbf{A} \) and \( \mathbf{D} \). (2x4 Marks) (d) Discuss in detail TWO methods you could use to determine if \( \mathrm{CB}(7) \) had bound one of the above molecules. Include what you would expect to see in the spectra/data. (2x4 Marks) (e) From your wider reading of the literature discuss an application of cucurbituril chemistry. (6 Marks)