Salt forms of amides : protonation and polymorphism of carbamazepine and cytenamide
Buist, Amanda and Kennedy, Alan and Shankland, Kenneth and Shankland, Norman and Spillman, Mark J. (2013) Salt forms of amides : protonation and polymorphism of carbamazepine and cytenamide. Crystal Growth and Design, 13 (11). pp. 5121-5127. ISSN 1528-7483 (https://doi.org/10.1021/cg401341y)
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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·H2O. A similar hydronium chloride species is the only product isolated after reaction of the carbamazepine analogue cytenamide with HCl generated in methanol.
ORCID iDs
Buist, Amanda, Kennedy, Alan ORCID: https://orcid.org/0000-0003-3652-6015, Shankland, Kenneth, Shankland, Norman and Spillman, Mark J.;-
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Item type: Article ID code: 46001 Dates: DateEvent2013Published7 October 2013Published OnlineSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 19 Nov 2013 17:10 Last modified: 18 Sep 2024 06:27 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/46001