X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one
The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one <b>1</b> and its unsaturated analogue 3-acetyloxazolin-2-one <b>3</b> show a planar imide nitrogen with the exocyclic C=O oriented &l...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/3/M1445 |
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| author | R. Alan Aitken Joe S. Logan Alexandra M. Z. Slawin |
| author_facet | R. Alan Aitken Joe S. Logan Alexandra M. Z. Slawin |
| author_sort | R. Alan Aitken |
| collection | DOAJ |
| description | The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one <b>1</b> and its unsaturated analogue 3-acetyloxazolin-2-one <b>3</b> show a planar imide nitrogen with the exocyclic C=O oriented <i>anti</i> 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(3<i>H</i>)-one <b>4</b>, 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 <i>R</i> factor. |
| first_indexed | 2024-03-09T23:03:20Z |
| format | Article |
| id | doaj.art-cf0abfc41b5545ca96958d91ea777de6 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T23:03:20Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
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| series | Molbank |
| spelling | doaj.art-cf0abfc41b5545ca96958d91ea777de62023-11-23T17:58:00ZengMDPI AGMolbank1422-85992022-09-0120223M144510.3390/M1445X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-oneR. Alan Aitken0Joe S. Logan1Alexandra M. Z. Slawin2EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKEaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKEaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKThe X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one <b>1</b> and its unsaturated analogue 3-acetyloxazolin-2-one <b>3</b> show a planar imide nitrogen with the exocyclic C=O oriented <i>anti</i> 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(3<i>H</i>)-one <b>4</b>, 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 <i>R</i> factor.https://www.mdpi.com/1422-8599/2022/3/M1445oxazolidin-2-oneoxazolin-2(3<i>H</i>)-oneX-ray structurehydrogen bonding |
| spellingShingle | R. Alan Aitken Joe S. Logan Alexandra M. Z. Slawin X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one Molbank oxazolidin-2-one oxazolin-2(3<i>H</i>)-one X-ray structure hydrogen bonding |
| title | X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one |
| title_full | X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one |
| title_fullStr | X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one |
| title_full_unstemmed | X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one |
| title_short | X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3<i>H</i>)-one |
| title_sort | x ray structures of 3 acetyloxazolidin 2 one 3 acetyloxazolin 2 one and oxazolin 2 3 i h i one |
| topic | oxazolidin-2-one oxazolin-2(3<i>H</i>)-one X-ray structure hydrogen bonding |
| url | https://www.mdpi.com/1422-8599/2022/3/M1445 |
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