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Title: Solvates and polymorphic phase transformations of 2-chloro-4-nitrobenzoic acid
Authors: Aitipamula, S.
Chow, P.S.
Tan, R.B.H. 
Issue Date: 7-Feb-2011
Citation: Aitipamula, S., Chow, P.S., Tan, R.B.H. (2011-02-07). Solvates and polymorphic phase transformations of 2-chloro-4-nitrobenzoic acid. CrystEngComm 13 (3) : 1037-1045. ScholarBank@NUS Repository.
Abstract: A previously unknown monohydrate and five solvates of an anti-HIV agent, 2-chloro-4-nitrobenzoic acid (CNBA), were discovered and characterized by various analytical techniques such as powder X-ray diffraction, single-crystal X-ray diffraction, differential scanning calorimetry, and thermogravimetric analysis. The solvates were readily obtained from the solvents 1,4-dioxane, dimethylsulfoxide, acetophenone, p-xylene and mesitylene. In the crystal structures of three of the solvates (1,4-dioxane, p-xylene and mesitylene solvates) the CNBA molecules form an acid-acid dimer motif and such motifs are stabilized via π⋯π stacking interactions. Slurry experiments confirmed the thermodynamic stability of Form I at room temperature. The results of desolvation experiments and a comparison of the crystal structures of the hydrate/solvates and the pure polymorphs indicate that the desolvation product does not necessarily contain a similar crystal structure to the solvate. Grinding experiments with catalytic amounts of various solvents suggest that Form II converts to Form I in most cases and both forms convert to the hydrate upon grinding with water. Grinding with 1,4-dioxane and mesitylene results in solvates and they transform to the more stable Form I upon extended grinding of 60 min. © 2011 The Royal Society of Chemistry.
Source Title: CrystEngComm
ISSN: 14668033
DOI: 10.1039/c0ce00361a
Appears in Collections:Staff Publications

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