Resonance-assisted amide protonation in dutasteride hydrochloride salt

Two novel crystal structures of dutasteride (hemihydrate and hydrochloride salt, crystallised before and after protonation respectively) are presented. Interestingly, in the dutasteride salt, only cyclic amide was protonated, but not phenyl amide. The protonation is attributed to increase in the ami...

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Bibliographic Details
Published in:CrystEngComm 2012-01, Vol.14 (7), p.2571-2578
Main Authors: Nanubolu, Jagadeesh Babu, Sridhar, Balasubramanian, Ravikumar, Krishnan
Format: Article
Language:English
Subjects:
Amides
Basicity
Crystal structure
Hydrochlorides
Phenyls
Protonation
Strength
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Summary:Two novel crystal structures of dutasteride (hemihydrate and hydrochloride salt, crystallised before and after protonation respectively) are presented. Interestingly, in the dutasteride salt, only cyclic amide was protonated, but not phenyl amide. The protonation is attributed to increase in the amide resonance that results in significant increase in the acceptor strength (or basicity) of amide O.
ISSN:1466-8033
1466-8033
DOI:10.1039/c2ce06421a