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Designing Acid/Acid Co-Crystals through the Application of Hammett Substituent Constants

Colin C. SeatonThe Molecular Materials Centre, School of Chemical Engineering and Analytical Sciences, The University of Manchester, PO Box 88, Manchester M60 1QD, U.KK. ChadwickDepartment of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MassachusettsG. SadiqThe Molecular Materials Centre, School of Chemical Engineering and Analytical Sciences, The University of Manchester, PO Box 88, Manchester M60 1QD, U.KKun GuoSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, ChinaRoger J. DaveyThe Molecular Materials Centre, School of Chemical Engineering and Analytical Sciences, The University of Manchester, PO Box 88, Manchester M60 1QD, U.K

2009en

ABI

Annotatsiya

The designed creation of co-crystals between substituted benzoic acids was investigated by the co-crystallization of 32 acid/acid combinations. Systems with differing signs of their Hammett substituent constants were found to successfully form co-crystals in 90% of the cases, while those with the same sign were successful in only 25% of the cases. The systems where single-crystal structure determination was possible displayed both co-crystal and salt formation, with the co-crystal systems displaying a tendency towards salt-like character with increasing difference in Hammett constant of the component species. Thus the bonding preferences and structure within acid/acid co-crystal systems may be tailored by selection of the functional groups upon the acid components.

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DOI: 10.1021/cg9011235

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