Structures of benzoic acids with substituted pyridines and quinolines: salt versus co-crystal formation

A series of five substituted benzoic acids with 10 substituted pyridines and quinolines have been crystallized so that their Δp K a , defined as p K a base –p K a acid , varied from −1.14 to +4.16. This spans the ‘uncertainty’ region for the formation of salt versus co-crystals. Although most of our...

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Bibliographic Details
Published in:CrystEngComm 2014-01, Vol.16 (26), p.5802-5810
Main Authors: Ramon, Gaëlle, Davies, Kate, Nassimbeni, Luigi R.
Format: Article
Language:English
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Summary:A series of five substituted benzoic acids with 10 substituted pyridines and quinolines have been crystallized so that their Δp K a , defined as p K a base –p K a acid , varied from −1.14 to +4.16. This spans the ‘uncertainty’ region for the formation of salt versus co-crystals. Although most of our results confirmed that structure formation of co-crystal versus salt parts at Δp K a ≈ 2, we report here a structure that does not follow the general rule and serves as a cautionary tale.
ISSN:1466-8033
1466-8033
DOI:10.1039/C3CE41963K