Abstract
A study of intramolecular hydrogen bonding in chloroform for a small combinatorial library of nine triamides with varying connecting chain length has been completed. The starting materials for the triamides are three diacids (succinic, glutaric, and adipic acid) and three amino acids (glycine, β-alanine, and γ-aminobutyric acid). The preferences for the head-to-tail type of folding pattern are identified for the smaller triamides (1 and 4). The preference for the head-to-tail folding pattern can be explained by the energetic superiority of an optimal hydrogen bond geometry in which the NH---O bond angle is near linearity. The β-alanine containing triamides 2, 5, and 8 are resistant to intramolecular hydrogen bonding, especially to nearest neighbor hydrogen bonding. At lower temperatures, triamides 2 and 5 exhibit a small population of head-to-tail type of folding, while triamide 8 shows a significant population of bifurcated conformation. Triamide 6, 7, and 9 prefer bicyclic structures involving nearest n...
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