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Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate
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dc.contributor.author | Tyumentsev, Mikhail S. | |
dc.contributor.author | Foreman, Mark R. St J. | |
dc.contributor.author | Steenari, Britt-Marie | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.date.accessioned | 2017-10-05T16:30:14Z | |
dc.date.available | 2017-10-05T16:30:14Z | |
dc.date.issued | 2017-10 | |
dc.identifier.citation | Tyumentsev , M S , Foreman , M R S J , Steenari , B-M & Slawin , A M Z 2017 , ' Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate ' , Acta Crystallographica Section E , vol. 73 , no. 10 , pp. 1576-1579 . https://doi.org/10.1107/S2056989017013962 | en |
dc.identifier.issn | 2056-9890 | |
dc.identifier.other | PURE: 251291444 | |
dc.identifier.other | PURE UUID: 7ad5aabc-1d53-4b30-918a-147dae46118d | |
dc.identifier.other | Bibtex: urn:dc60207336c7beb1bc68c564b046ba8d | |
dc.identifier.other | Scopus: 85044786230 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861555 | |
dc.identifier.other | WOS: 000412026700041 | |
dc.identifier.uri | https://hdl.handle.net/10023/11809 | |
dc.description | The research leading to these results received funding from the European Community's Seventh Framework Programme ([FP7/2007–2013]) under grant agreement No. 607411 (MC-ITN EREAN: European Rare Earth Magnet Recycling Network). | en |
dc.description.abstract | The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45(3) and 83.30(3)°, respectively]. The C—C and C—O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O···O contact [2.756(2)Å], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C—H···O interactions are observed, which link the molecules into [100] chains. | |
dc.format.extent | 4 | |
dc.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section E | en |
dc.rights | © 2017 The Authors. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. | en |
dc.subject | Crystal structure | en |
dc.subject | 3-alkylidene-3H-isobenzofuran-1-ones | en |
dc.subject | Delocalization | en |
dc.subject | Enolate | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1107/S2056989017013962 | |
dc.description.status | Peer reviewed | en |
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