Dinitrobenzoyl hydrogen bond

The pioneering work in the area of chiral 77-donor and 77-acceptor phases was done by Pirkle and co-workers,98,99 and the most frequently used 77-acceptor phase is still an (/ )-7V-(3,5-dinitrobenzoyl)phenylglycine phase, the so-called Pirkle phase. With these stationary phases, chiral recognition is based on 77-77 interactions, dipole stacking interactions, and hydrogen bonding.100... 

This situation has been described by Pirkle et al. (13,14) for a type I CSp (J )-N-(10-undecanoyl)-a-(6,7-dimethyI-l-naphthyl)-isobutyl amine, and fora homologous series of solutes based on dinitrobenzoyl derivatives of 1-phenylalkyl amines. The experimental results indicated that two different interaction mechanisms were responsible for the formation of the solute/CSP complexes. One mechanism was based on dipole-dipole interactions that resulted in diastereomeric complexes where the (R)-solute/CSP complex was more stable, whereas the other was due to hydrogen-bonding interactions and produced a situation where the (S)-solute/CSP complex was more stable. 

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