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X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one

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Aitken_2022_molbank_X_ray_structures_CC.pdf (2.112Mb)
Date
14/09/2022
Author
Aitken, R Alan
Logan, Joe S.
Slawin, Alexandra Martha Zoya
Keywords
Oxazolidin-2-one
Oxazolin-2(3H)-one
X-ray structure
Hydrogen bonding
QD Chemistry
DAS
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Abstract
The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4 , exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor.
Citation
Aitken , R A , Logan , J S & Slawin , A M Z 2022 , ' X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3 H )-one ' , Molbank , vol. 2022 , no. 3 , M1445 . https://doi.org/10.3390/M1445
Publication
Molbank
Status
Peer reviewed
DOI
https://doi.org/10.3390/M1445
ISSN
1422-8599
Type
Journal article
Rights
Copyright: © 2022 by the authors. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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  • University of St Andrews Research
URL
https://www.mdpi.com/1422-8599/2022/3/M1445/htm
URI
http://hdl.handle.net/10023/26017

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