Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 5121-5127 |
| Number of pages | 7 |
| Journal | Crystal Growth and Design |
| Volume | 13 |
| Issue number | 11 |
| Early online date | 7 Oct 2013 |
| DOIs | |
| Publication status | Published - 2013 |
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Salt forms of amides : protonation and polymorphism of carbamazepine and cytenamide. / Buist, Amanda; Kennedy, Alan; Shankland, Kenneth; Shankland, Norman; Spillman, Mark J.
In: Crystal Growth and Design, Vol. 13, No. 11, 2013, p. 5121-5127.Research output: Contribution to journal › Article
TY - JOUR
T1 - Salt forms of amides
T2 - protonation and polymorphism of carbamazepine and cytenamide
AU - Buist, Amanda
AU - Kennedy, Alan
AU - Shankland, Kenneth
AU - Shankland, Norman
AU - Spillman, Mark J.
PY - 2013
Y1 - 2013
N2 - In situ generation of HCl or HBr in alcohol leads to O-protonation of theamide 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 onlyproduct isolated after reaction of the carbamazepine analogue cytenamide with HCl generated in methanol.
AB - In situ generation of HCl or HBr in alcohol leads to O-protonation of theamide 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 onlyproduct isolated after reaction of the carbamazepine analogue cytenamide with HCl generated in methanol.
UR - http://www.scopus.com/inward/record.url?scp=84887723780&partnerID=8YFLogxK
UR - http://pubs.acs.org/journal/cgdefu
U2 - 10.1021/cg401341y
DO - 10.1021/cg401341y
M3 - Article
VL - 13
SP - 5121
EP - 5127
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 11
ER -