Indenone and cyclopentadienone energetics via mass spectrometry and computations: Are these species antiaromatic or “merely” nonaromatic?

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dc.contributor.authorFattahi, Alireza
dc.contributor.authorLiebman, Joel F.
dc.contributor.authorMiranda, Margarida S.
dc.contributor.authorMorais, Victor M.F.
dc.contributor.authorMatos, M. Agostinha R.
dc.contributor.authorLis, Lev
dc.contributor.authorKass, Steven R.
dc.date.accessioned2018-10-01T14:01:20Z
dc.date.available2018-10-01T14:01:20Z
dc.date.issued2014-06-14
dc.description.abstractThe heat of hydrogenation of indenone was measured via two partially independent thermodynamic cycles by carrying out energetic measurements (i.e., electron affinities, proton affinities and ionization potentials) on both negative and positive ions (ΔH°(H2) = 17.8 ± 5.5 and 17.5 ± 5.7 kcal mol⁻¹, respectively). High level G3 computations were also carried out to provide the heats of formation of indenone (16.8 kcal mol⁻¹) and cyclopentadienone (14.0 kcal mol⁻¹). These 4n π electron systems are found to be nonaromatic in contrast to previous views. A recent report on cyclopropenyl anion (J. Org. Chem. 2013, 78, 7370–7372) indicates that this ion is also nonaromatic, and suggests that NMR ring currents and nucleus independent chemical shift (NICS) calculations do not correlate with the energetic criterion for antiaromatic compounds.en_US
dc.description.sponsorshipSupport from the National Science Foundation and the Minnesota Supercomputer Institute for Advanced Computational Research are gratefully acknowledged.en_US
dc.description.urihttps://www.sciencedirect.com/science/article/pii/S1387380614002176#!en_US
dc.format.extent5 pagesen_US
dc.genrejournal articleen_US
dc.identifierdoi:10.13016/M2PN8XJ94
dc.identifier.citationAlireza Fattahi, Joel F. Liebman, Margarida S. Miranda, Victor M.F. Morais, M. Agostinha R. Matos, Lev Lis, Steven R. Kass Reprint of “Indenone and cyclopentadienone energetics via mass spectrometry and computations: Are these species antiaromatic or “merely” nonaromatic?” International Journal of Mass Spectrometry, Volume 378, 15 February 2015, Pages 175-179, https://doi.org/10.1016/j.ijms.2014.06.011en_US
dc.identifier.urihttps://doi.org/10.1016/j.ijms.2014.06.011
dc.identifier.urihttp://hdl.handle.net/11603/11421
dc.language.isoen_USen_US
dc.publisherScienceDirecten_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.subjectFTMSen_US
dc.subjectAntiaromaticityen_US
dc.subjectCyclopentadienoneen_US
dc.subjectIndenoneen_US
dc.subjectHeat of hydrogenationen_US
dc.subjectUMBC High Performance Computing Facility (HPCF)en_US
dc.titleIndenone and cyclopentadienone energetics via mass spectrometry and computations: Are these species antiaromatic or “merely” nonaromatic?en_US
dc.typeTexten_US

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