Foldamers, much like the biomolecules they model, have repeating units forming well-defined conformations such as helices, β-sheets and macrocycles. Aromatic oligourea foldamers in particular represent one class of foldamers whose basic motif comprises repeating units of phenyl and urea groups. As structure influences function and mechanism, it is important to study their conformational preferences, starting with their basic monomeric unit. This work focuses on the conformational behavior of N,N’-diphenylurea in solvent environments of different polarities such as chloroform, acetonitrile, dimethylsulfoxide, and methanol. In conjunction with molecular dynamics simulations, 1H NMR spectroscopy (focusing on the N-H resonance) at different temperatures were carried out in order to determine the rotational barriers around the α- and β-dihedral angles of N,N’-diphenylurea, thus providing molecular insight into their conformational propensities in different solvent environments. 1H NMR data show a general upfield chemical shift of the N-H resonance with increasing temperature for all four solvents. Results from this study provide physical insight into the stabilities of the conformers as influenced by the molecular nature of the environment.

Solvent environment effects on the conformational changes of N,N’-diphenylurea

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