Journal
CRYSTAL GROWTH & DESIGN
Volume 13, Issue 11, Pages 5121-5127Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cg401341y
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Funding
- University of Reading
- STFC Centre for Molecular Structure and Dynamics
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In situ generation of HCl or HBr in alcohol leads to O-protonation of the amide group of carbamazepine. Six salt phases have been produced using this method and their crystal structures determined by single crystal diffraction. A new polymorph of carbamazepine hydrochloride is described as are two polymorphs of carbamazepine hydrobromide. All are protonated at the amide O atom to give RC(OH)NH2 cations. Prolonged exposure to air results in addition of water to the solid salt forms. Such hydration of carbamazepine hydrobromide simply gives a monohydrated phase, but similar treatment of the equivalent hydrochloride results in partial loss of HCl and the transfer of the remaining proton from the amide group to water to give [carbamazepine][H3O](0.5)[Cl](0.5)center dot H2O. A similar hydronium chloride species is the only product isolated after reaction of the carbamazepine analogue cytenamide with HCl generated in methanol.
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