The following compound is an amino acid derivative (Chapter 25). In solution, molecules

Chapter 2, Problem 2.75

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The following compound is an amino acid derivative (Chapter 25). In solution, molecules of this compound show a tendency to stick together, or self-assemble, via a series of intermolecular hydrogen bonds. During self-assembly, the growing aggregate can entrap molecules of liquid, thereby forming a gel (J. Am. Chem. Soc. 2009, 131, 1147811484). N N O N O N N O O N H H H H H H (a) Each of the six hydrogen atoms bound directly to nitrogen can form a hydrogen bond, but Hs that are on the amides can form stronger hydrogen bonds than Hs on the amines. Explain why this is so using resonance. (b) Draw the intermolecular hydrogen bonds that form during selfassembly. Do this by drawing three molecules stacked directly on top of each other, each in the orientation shown. Then, draw hydrogen bonds from the central molecule to each of the other two molecules, showing eight intermolecular H bonds between amide Hs on one molecule to amide Os on adjacent molecules.