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dc.contributor.authorSkotnicka, Agnieszka
dc.contributor.authorKolehmainen, Erkki
dc.contributor.authorCzelen, Przemyslaw
dc.contributor.authorValkonen, Arto
dc.contributor.authorGawinecki, Ryszard
dc.date.accessioned2016-01-25T06:56:45Z
dc.date.available2016-01-25T06:56:45Z
dc.date.issued2013
dc.identifier.citationSkotnicka, A., Kolehmainen, E., Czelen, P., Valkonen, A., & Gawinecki, R. (2013). Synthesis and Structural Characterization of Substituted 2-Phenacylbenzoxazoles. <i>International Journal of Moleclular Sciences</i>, <i>14</i>(3), 4444-4460. <a href="https://doi.org/10.3390/ijms14034444" target="_blank">https://doi.org/10.3390/ijms14034444</a>
dc.identifier.otherCONVID_22357798
dc.identifier.otherTUTKAID_55959
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/48445
dc.description.abstract1 H and 13C NMR spectra of eleven 2-phenacylbenzoxazoles (ketimine form) show that their CDCl3-solutions contains also (Z)-2-(benzo[d]oxazol-2-yl)-1-phenylethenols (enolimine form). Intramolecular hydrogen bonding in the latter tautomer was found to be significantly weaker than that one in respective (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines. Integrals of the 1 H NMR signals were used to evaluate the molar ratio of the tautomers. Strong electron-donating substituents were found to stabilize the ketimine tautomer. pKT (negative logarithm of the equilibrium constant, KT = [ketimine]/[enolimine]) was found to be linearly dependent on the Hammett substituent constant σ. The results of the MP2 ab initio calculations reveal enolimine including an intramolecular OH…N hydrogen bond to be the most stable form both with electron-donor and electron-acceptor substituents. The stability of ketimines is an intermediate of those found for enolimines and enaminones i.e., (E)-2-(benzo[d]oxazol-2(3H)-ylidene)-1-phenylethanones. 13C CPMAS NMR spectral data reveal that in the crystalline state the ketimine tautomer is predominant in p-NMe2 substituted congener. On the other hand, enolimine forms were detected there when the substituent has less electron-donating character or when it is an electron-acceptor by character.
dc.language.isoeng
dc.publisherMDPI AG
dc.relation.ispartofseriesInternational Journal of Moleclular Sciences
dc.subject.other2-fenasyylibentsoksatsoli
dc.subject.other2-phenyacylbenzoxazole
dc.titleSynthesis and Structural Characterization of Substituted 2-Phenacylbenzoxazoles
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201601191164
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2016-01-19T16:15:29Z
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange4444-4460
dc.relation.issn1422-0067
dc.relation.numberinseries3
dc.relation.volume14
dc.type.versionpublishedVersion
dc.rights.copyright© the Authors, 2013. This is an open access article distributed under the Creative Commons Attribution License (CC BY).
dc.rights.accesslevelopenAccessfi
dc.rights.urlhttp://creativecommons.org/licenses/by/3.0/
dc.relation.doi10.3390/ijms14034444
dc.type.okmA1


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© the Authors, 2013. This is an open access article distributed under the Creative Commons Attribution License (CC BY).
Except where otherwise noted, this item's license is described as © the Authors, 2013. This is an open access article distributed under the Creative Commons Attribution License (CC BY).