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Article
Sulfur and Selenium Ylide Bond Enthalpies
The Journal of Organic Chemistry
  • Stacey A. Stoffregen, Iowa State University
  • Ryan D. McCulla, Iowa State University
  • Robert Wilson, Iowa State University
  • Samuel Cercone, Iowa State University
  • Jennifer Miller, Iowa State University
  • William S. Jenks, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
9-29-2007
DOI
10.1021/jo0711438
Abstract
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, S,C-sulfonium ylides, and selenoxides. Selenoxides have BDEs about 10 kcal/mol smaller than the corresponding sulfoxides. N-H sulfilimines and CH2-S,C-sulfonium ylides have low BDEs, unless the sulfilimine or S,C-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.
Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 72(22); 8235-8242. Doi: 10.1021/jo0711438. Copyright 2007 American Chemical Society.

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Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Stacey A. Stoffregen, Ryan D. McCulla, Robert Wilson, Samuel Cercone, et al.. "Sulfur and Selenium Ylide Bond Enthalpies" The Journal of Organic Chemistry Vol. 72 Iss. 22 (2007) p. 8235 - 8242
Available at: http://works.bepress.com/william_jenks/12/