From molecular salt to pseudo CAB cocrystal: Expanding solid-state landscape of carboxylic acids based on charge-assisted COOH⋯COO¯ hydrogen bonds

Benyong Lou; Sathyanarayana Reddy Perumalla; Changquan Calvin Sun

doi:10.1016/j.molstruc.2015.07.008

From molecular salt to pseudo CAB cocrystal: Expanding solid-state landscape of carboxylic acids based on charge-assisted COOH⋯COO¯ hydrogen bonds

Benyong Lou, Sathyanarayana Reddy Perumalla, Changquan Calvin Sun

Pharmaceutics

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Abstract Using three carboxylic acids, we show that the COOH⋯COO¯ synthon is robust for directing the cocrystallization between a carboxylic acid and a carboxylate of either the same or a chemically different molecule to form a CAB or pseudo CAB cocrystal, respectively. For a given carboxylic acid and a counterion, only one salt could be prepared. However, additional one CAB cocrystals and two pseudo CAB cocrystals could be prepared based on the COOH⋯COO¯ synthon. The same synthon has the potential to enable the preparation of additional molecular pseudo CAB cocrystals using other chemically distinct carboxylic acids. This significantly increased number of solid forms highlights the values of charge-assisted synthons, such as COOH⋯COO¯, in crystal engineering for expanding the range of material properties of a given molecule for optimum performance in product design.

Original language	English (US)
Article number	21663
Pages (from-to)	516-522
Number of pages	7
Journal	Journal of Molecular Structure
Volume	1099
DOIs	https://doi.org/10.1016/j.molstruc.2015.07.008
State	Published - Jul 17 2015

Bibliographical note

Funding Information:
B. Lou is grateful to the support from Fujian Provincial Overseas Scholarship and Research Project for Young and Middle-aged Faculty of Fujian Province ( JA14250 ). We are grateful for resources from the University of Minnesota Supercomputing Institute. X-Ray diffraction experiments were performed using a crystal diffractometer acquired through NSF-MRI Award CHE-1229400.

Publisher Copyright:
© 2015 Elsevier B.V.

Keywords

CAB cocrystal
Carboxylic acid
Charge-assisted
Synthon

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title = "From molecular salt to pseudo CAB cocrystal: Expanding solid-state landscape of carboxylic acids based on charge-assisted COOH⋯COO¯ hydrogen bonds",

abstract = "Abstract Using three carboxylic acids, we show that the COOH⋯COO¯ synthon is robust for directing the cocrystallization between a carboxylic acid and a carboxylate of either the same or a chemically different molecule to form a CAB or pseudo CAB cocrystal, respectively. For a given carboxylic acid and a counterion, only one salt could be prepared. However, additional one CAB cocrystals and two pseudo CAB cocrystals could be prepared based on the COOH⋯COO¯ synthon. The same synthon has the potential to enable the preparation of additional molecular pseudo CAB cocrystals using other chemically distinct carboxylic acids. This significantly increased number of solid forms highlights the values of charge-assisted synthons, such as COOH⋯COO¯, in crystal engineering for expanding the range of material properties of a given molecule for optimum performance in product design.",

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author = "Benyong Lou and Perumalla, {Sathyanarayana Reddy} and Sun, {Changquan Calvin}",

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AU - Sun, Changquan Calvin

N1 - Funding Information: B. Lou is grateful to the support from Fujian Provincial Overseas Scholarship and Research Project for Young and Middle-aged Faculty of Fujian Province ( JA14250 ). We are grateful for resources from the University of Minnesota Supercomputing Institute. X-Ray diffraction experiments were performed using a crystal diffractometer acquired through NSF-MRI Award CHE-1229400. Publisher Copyright: © 2015 Elsevier B.V.

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N2 - Abstract Using three carboxylic acids, we show that the COOH⋯COO¯ synthon is robust for directing the cocrystallization between a carboxylic acid and a carboxylate of either the same or a chemically different molecule to form a CAB or pseudo CAB cocrystal, respectively. For a given carboxylic acid and a counterion, only one salt could be prepared. However, additional one CAB cocrystals and two pseudo CAB cocrystals could be prepared based on the COOH⋯COO¯ synthon. The same synthon has the potential to enable the preparation of additional molecular pseudo CAB cocrystals using other chemically distinct carboxylic acids. This significantly increased number of solid forms highlights the values of charge-assisted synthons, such as COOH⋯COO¯, in crystal engineering for expanding the range of material properties of a given molecule for optimum performance in product design.

AB - Abstract Using three carboxylic acids, we show that the COOH⋯COO¯ synthon is robust for directing the cocrystallization between a carboxylic acid and a carboxylate of either the same or a chemically different molecule to form a CAB or pseudo CAB cocrystal, respectively. For a given carboxylic acid and a counterion, only one salt could be prepared. However, additional one CAB cocrystals and two pseudo CAB cocrystals could be prepared based on the COOH⋯COO¯ synthon. The same synthon has the potential to enable the preparation of additional molecular pseudo CAB cocrystals using other chemically distinct carboxylic acids. This significantly increased number of solid forms highlights the values of charge-assisted synthons, such as COOH⋯COO¯, in crystal engineering for expanding the range of material properties of a given molecule for optimum performance in product design.

KW - CAB cocrystal

KW - Carboxylic acid

KW - Charge-assisted

KW - Synthon

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From molecular salt to pseudo CAB cocrystal: Expanding solid-state landscape of carboxylic acids based on charge-assisted COOH⋯COO¯ hydrogen bonds

Abstract

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Keywords

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