Modeling of the following compounds
bis-(
N--amido-L-phenylalaninyl)-1,1-cyclopropane dicarboxylate,
3, and
bis-(
N--amido-L-phenylalaninyl)-1,1-cyclobutane dicarboxylate,
4, were undertaken. The study involved construction and optimization of the precursory 1,1-dicarboxaldehydes and continued stepwise via the 1,1-dicarboxamides, the
bis-N-(methyl)dicarboxamides, the
bis(
N--amidoglycinyl) dicarboxylates, the
bis(
N--amido-L-alaninyl) dicarboxylates and onto the targeted
bis(
N--amido-L-phenylalaninyl) dicarboxylates. Using the X-ray crystal structure of
4 (i.e.,
4X) as a guide, we found that our approach was not able to reproduce the packable conformer of
4, via the computational methods employed. Nevertheless, an enhanced understanding of the intramolecular hydrogen bonding patterns available to these systems was obtained from IR and VT-NMR studies. In summary, the conformational preferences found in the 1,1-disubstituted cycloalkanes (
3 and
4) direct their respective self-assembly processes by controlling the orientation of their amide NH populations.
相似文献