Photochemical Valence Isomerization to High Energy Products—Bicyclobutanes and Oxabicyclobutanes

dc.contributor.authorRágyanszki, Anita
dc.contributor.authorFiser, Béla
dc.contributor.authorLee-Ruff, Edward
dc.contributor.authorLiebman, Joel F.
dc.date.accessioned2021-07-06T18:08:15Z
dc.date.available2021-07-06T18:08:15Z
dc.date.issued2021-06-18
dc.description.abstractDFT calculations were used to determine the structures and energies of bicyclobutane and oxabicyclobutane as valence isomers derived from electronic excitation of their corresponding precursors, 1,3-butadiene and acrolein, respectively. Proton affinities of these strained compounds were determined and compared with their simple ring components, cyclopropane and ethylene oxide. The basicity as determined from proton affinities showed that bicyclobutane is the most basic saturated hydrocarbon, even more basic than oxabicyclobutane. Strain energies of these valence tautomers were computed which showed oxabicyclobutane to be significantly more strained than bicyclobutane. Qualitative reasons are provided to account for the difference in strain energies.en_US
dc.description.sponsorshipBF thanks for the support by the UNKP-20-4 New ´ National Excellence Program of The Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund (Hungary). This research is supported by the European Union and the Hungarian State, co-financed by the European Regional Development Fund in the framework of the GINOP-2.3.4-15-2016-00004 project, which aimed to promote the cooperation between higher education and industry. This research was enabled in part by the support provided by SHARCNET (www.sharcnet.ca/) and Compute Canada (www.computeca nada.ca). AR acknowledge the National Talent Programme, Hungary, for the financial support.en_US
dc.description.urihttps://onlinelibrary.wiley.com/doi/10.1111/php.13472en_US
dc.format.extent2 filesen_US
dc.genrejournal articles postprintsen_US
dc.identifierdoi:10.13016/m2u9yo-0r7t
dc.identifier.citationRágyanszki, Anita et al.; Photochemical Valence Isomerization to High Energy Products—Bicyclobutanes and Oxabicyclobutanes; Photochemistry & Photobiology, 18 June, 2021; https://doi.org/10.1111/php.13472en_US
dc.identifier.urihttps://doi.org/10.1111/php.13472
dc.identifier.urihttp://hdl.handle.net/11603/21863
dc.language.isoen_USen_US
dc.publisherWiley Online Libraryen_US
dc.relation.isAvailableAtThe University of Maryland, Baltimore County (UMBC)
dc.relation.ispartofUMBC Chemistry & Biochemistry Department Collection
dc.relation.ispartofUMBC Faculty Collection
dc.rightsThis item is likely protected under Title 17 of the U.S. Copyright Law. Unless on a Creative Commons license, for uses protected by Copyright Law, contact the copyright holder or the author.
dc.rightsThis is the peer reviewed version of the following article: Rágyanszki, Anita et al.; Photochemical Valence Isomerization to High Energy Products Bicyclobutanes and Oxabicyclobutanes; Photochemistry & Photobiology, 18 June, 2021; https://onlinelibrary.wiley.com/doi/10.1111/php.13472, which has been published in final form at https://doi.org/10.1111/php.13472.
dc.rightsAccess to this item will begin on 2022-06-18
dc.titlePhotochemical Valence Isomerization to High Energy Products—Bicyclobutanes and Oxabicyclobutanesen_US
dc.typeTexten_US

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