Supramolecular synthesis based on a combination of hydrogen- and halogen bonds.

Cryst Growth Des

Contribution from the Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, Kansas, 66506.

Published: January 2009

AI Article Synopsis

  • A family of supramolecular reagents was created using pyridine and amino-pyrimidine to react with iodo- or bromo-substituted benzoic acids, leading to larger molecular architectures.
  • The primary building blocks were formed through strong hydrogen bonds, achieving a 100% supramolecular yield, while halogen bonds helped organize these structures into 1-D and 2-D arrangements with a 71% yield.
  • The study shows the effectiveness of combining different non-covalent interactions to create complex and structured molecular networks reliably.

Article Abstract

A family of supramolecular reagents containing two different binding sites, pyridine and amino-pyrimidine, were allowed to react with iodo- or bromo-substituted benzoic acids in order to assemble individual molecules into larger architectures with precise intermolecular interactions, using a combination of hydrogen- and halogen-bonds. The hydrogen-bond based amino-pyrimidine/carboxylic acid or amino-pyrimidinium/carboxylate synthons are responsible for the assembly of the primary structural motif in every case (7/7 times, 100% supramolecular yield), while Icdots, three dots, centeredN, Brcdots, three dots, centeredN, and Icdots, three dots, centeredO, halogen bonds play a structural supporting role by organizing these supermolecules into extended 1-D and 2-D architectures (5/7 times, 71% supramolecular yield). These results illustrate how two different non-covalent interactions can be employed side-by-side in the reliable construction of extended molecular solid-state networks with predictable connectivity and dimensionality.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2724020PMC
http://dx.doi.org/10.1021/cg8006712DOI Listing

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