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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

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A high-yielding supramolecular reaction.

Christer B Aakeröy¹, Alicia M Beatty, Brian A Helfrich

¹Department of Chemistry, Kansas State University, Manhattan, Kansas, USA. aakeroy@ksu.edu

Journal of the American Chemical Society

|November 28, 2002

Summary

Iso-nicotinamide forms consistent hydrogen-bonded "supermolecules" with carboxylic acids. This supramolecular reagent reliably creates discrete molecular assemblies, even with dicarboxylic acids, yielding predictable structures.

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Area of Science:

Crystal Engineering
Supramolecular Chemistry
Materials Science

Background:

Hydrogen bonding plays a crucial role in molecular self-assembly.
Iso-nicotinamide is a versatile molecule with amide and pyridine functionalities.
Carboxylic acids are common building blocks in supramolecular chemistry.

Purpose of the Study:

To investigate the hydrogen-bonding preferences of iso-nicotinamide with various carboxylic acids.
To characterize the resulting supramolecular structures formed.
To assess the reliability of iso-nicotinamide as a supramolecular reagent.

Main Methods:

X-ray crystal structure determination of twelve cocrystals.
Analysis of hydrogen bond patterns and supramolecular synthons.
Comparison of structures formed with mono- and dicarboxylic acids.

Main Results:

A consistent pattern of hydrogen-bond preferences was observed.
Discrete "supermolecules" formed between iso-nicotinamide and monocarboxylic acids.
Carboxylic acid-pyridine and amide-amide interactions were dominant synthons.
Dicarboxylic acids led to infinite assemblies or hexameric complexes.
Well-defined and robust connectivity was achieved in all cases.

Conclusions:

Iso-nicotinamide acts as a reliable supramolecular reagent.
Predictable supermolecule formation is achievable with carboxylic acids.
The observed hydrogen bonding patterns are robust across diverse chemical functionalities.