Sulfur and Selenium Ylide Bond Enthalpies

dc.contributor.author Stoffregen, Stacey
dc.contributor.author McCulla, Ryan
dc.contributor.author Jenks, William
dc.contributor.author Wilson, Robert
dc.contributor.author Cercone, Samuel
dc.contributor.author Miller, Jennifer
dc.contributor.author Jenks, William
dc.contributor.department Chemistry
dc.date 2018-02-17T06:46:22.000
dc.date.accessioned 2020-06-30T01:18:00Z
dc.date.available 2020-06-30T01:18:00Z
dc.date.copyright Mon Jan 01 00:00:00 UTC 2007
dc.date.issued 2007-09-29
dc.description.abstract <p>The bond dissociation enthalpies (BDEs) of sulfur and selenium ylides have been estimated by applying MP2/6-311++G(3df,2p)//MP2/6-31G(d,p), G3, and other computational methods. Computed sulfoxide bond enthalpies were compared to experimental results to ensure the reliability of the computational methods before extending to related compounds. The examined ylides include the following:  sulfoxides, sulfilimines, <em>S</em>,<em>C</em>-sulfonium ylides, and selenoxides. Selenoxides have BDEs about 10 kcal/mol smaller than the corresponding sulfoxides. <em>N</em>-H sulfilimines and CH2-<em>S</em>,<em>C</em>-sulfonium ylides have low BDEs, unless the sulfilimine or <em>S</em>,<em>C</em>-sulfonium ylide is stabilized by an electronegative substituent on N or C, respectively. Incorporation of the S or Se into a thiophene or selenophene-type ring lowers the BDE for the ylide.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>The Journal of Organic Chemistry</em>, 72(22); 8235-8242. Doi: <a href="http://dx.doi.org/10.1021/jo0711438" target="_blank">10.1021/jo0711438</a>. Copyright 2007 American Chemical Society.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/156/
dc.identifier.articleid 1156
dc.identifier.contextkey 7886579
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/156
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/14591
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/156/0-2007_JenksWS_ACS_License_SulfurSeleniumYlide.pdf|||Fri Jan 14 20:43:35 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/156/2007_JenksWS_SulfurSeleniumYlide.pdf|||Fri Jan 14 20:43:36 UTC 2022
dc.source.uri 10.1021/jo0711438
dc.subject.disciplines Chemistry
dc.subject.disciplines Organic Chemistry
dc.subject.disciplines Other Chemistry
dc.subject.disciplines Polymer Chemistry
dc.title Sulfur and Selenium Ylide Bond Enthalpies
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 4bd6268b-7134-4d6d-9050-46681c12c965
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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