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The <jats:italic>X<\/jats:italic>SS<jats:italic>X<\/jats:italic> isomers are more stable than the <jats:italic>X<\/jats:italic><jats:sub>2<\/jats:sub>SS isomers for all substituents. The energy gap \u0394<jats:italic>E<\/jats:italic>(<jats:italic>X<\/jats:italic>) between the two isomers increases (i.e., <jats:italic>X<\/jats:italic>SS<jats:italic>X<\/jats:italic> becomes more stable with respect to <jats:italic>X<\/jats:italic><jats:sub>2<\/jats:sub>SS), and the <jats:italic>S<\/jats:italic>\uf8ff<jats:italic>S<\/jats:italic> bond contracts in the series for <jats:italic>X<\/jats:italic> = F, Cl, CH<jats:sub>3<\/jats:sub>, H. The results are interpreted by means of natural population analysis (NPA) (e.g., the interaction between the disulfide moiety S<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-stack-1.gif\" xlink:title=\"urn:x-wiley:01928651:media:JCC540160410:tex2gif-stack-1\" \/> and the two substituents <jats:italic>X<\/jats:italic>\u00b7). The bonding in the hypervalent <jats:italic>X<\/jats:italic><jats:sub>2<\/jats:sub>SS species is similar to the bonding in the nonhypervalent <jats:italic>X<\/jats:italic>SS<jats:italic>X<\/jats:italic> and does not involve a special role for sulfur\u20103<jats:italic>d<\/jats:italic> orbitals. These orbitals acquire only minimal populations and are not to be conceived as valence orbitals. The DFT and conventional <jats:italic>ab initio<\/jats:italic> results, X\u03b1\/DZP and MP2\/6\u201031G** optimized structures and isomerization energies (at the highest levels of both methods), agree well. \u00a9 1995 by John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/jcc.540160410","type":"journal-article","created":{"date-parts":[[2005,1,2]],"date-time":"2005-01-02T00:41:51Z","timestamp":1104626511000},"page":"465-477","source":"Crossref","is-referenced-by-count":50,"title":["Theoretical investigation of the relative stabilities of <i>X<\/i>SS<i>X<\/i> and <i>X<\/i><sub>2<\/sub>SS isomers (<i>X<\/i> = F, Cl, H, and CH<sub>3<\/sub>)"],"prefix":"10.1002","volume":"16","author":[{"given":"F. 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