Title
Molecular modeling of the 1,1-cyclopropane- and 1,1-cyclobutanedicarboxamide systems. Insights into the self-assembly of diamide diacids in water
Abbreviated Journal Title
Struct. Chem.
Keywords
self-assembly; cyclopropane; cyclobutane; microcapsules; microspheres; SEMIEMPIRICAL METHODS; RECOGNITION; ACID; CONFORMATION; OPTIMIZATION; PARAMETERS; GEOMETRY; NMR; IR; Chemistry, Multidisciplinary; Chemistry, Physical; Crystallography
Abstract
Modeling of the following compounds bis-(N-alpha-amido-L-phenylalaninyl)- 1,1- cyclopropane dicarboxylate, 3, and bis-(N-alpha- 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-alpha-amidoglycinyl) dicarboxylates, the bis(N-alpha-amido-L-alaninyl) dicarboxylates and onto the targeted bis(N-alpha-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.
Journal Title
Structural Chemistry
Volume
13
Issue/Number
5-6
Publication Date
1-1-2002
Document Type
Article
Language
English
First Page
443
Last Page
453
WOS Identifier
ISSN
1040-0400
Recommended Citation
"Molecular modeling of the 1,1-cyclopropane- and 1,1-cyclobutanedicarboxamide systems. Insights into the self-assembly of diamide diacids in water" (2002). Faculty Bibliography 2000s. 3097.
https://stars.library.ucf.edu/facultybib2000/3097
Comments
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