Salt and ionic cocrystalline forms of amides: protonation of carbamazepine in aqueous media
Data(s) |
28/10/2015
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Resumo |
The products of reactions of the pharmaceutical amide carbamazepine (CBZ) with strong acids under aqueous conditions were investigated by both powder and single crystal X-ray diffraction. Despite previous claims to the contrary, it was found that salt forms with CBZ protonated at the amide O atom could be isolated from reactions with both HCl and HBr. These forms include the newly identified hydrate phase [CBZ(H)][Cl]·H O. Reactions with other mineral acids (HI and HBF ) gave ionic cocrystalline (ICC) forms (CBZ· [acridinium][I ]·2.5I and CBZ·[H O ] [BF ] ·H O) as well as the salt form CBZ·[CBZ(H)][BF ]·0.5H O. Reaction 2 4 3 2 5 2 0.25 4 0.25 2 4 2 of CBZ with a series of sulfonic acids also gave salt forms, namely, [CBZ(H)][O SC H ], [CBZ(H)][O SC H (OH)]· 3 6 5 3 6 4 0.5H O, [CBZ(H)] [O SCH CH SO ], and [CBZ(H)][O SC H (OH) (COOH)]·H O. CBZ and protonated CBZ(H) 2 2 3 2 2 3 3 6 3 2 moieties can be differentiated in the solid state both by changes to molecular geometry and by differing packing preferences |
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text |
Identificador |
http://centaur.reading.ac.uk/48596/1/Buist%28CBZH%29.pdf Buist, A. R., Edgeley, D. S., Kabova, E. A. <http://centaur.reading.ac.uk/view/creators/90007241.html>, Kennedy, A. R., Hooper, D., Rollo, D. G., Shankland , K. and Spillman, M. J. <http://centaur.reading.ac.uk/view/creators/90005810.html> (2015) Salt and ionic cocrystalline forms of amides: protonation of carbamazepine in aqueous media. Crystal Growth & Design, 15 (12). pp. 5955-5962. ISSN 1528-7483 doi: 10.1021/acs.cgd.5b01223 <http://dx.doi.org/10.1021/acs.cgd.5b01223> |
Idioma(s) |
en |
Publicador |
American Chemical Society |
Relação |
http://centaur.reading.ac.uk/48596/ creatorInternal Kabova, Elena A. creatorInternal Spillman, Mark J. 10.1021/acs.cgd.5b01223 |
Tipo |
Article PeerReviewed |