{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,10,26]],"date-time":"2023-10-26T05:04:22Z","timestamp":1698296662824},"reference-count":35,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2004,9,7]],"date-time":"2004-09-07T00:00:00Z","timestamp":1094515200000},"content-version":"vor","delay-in-days":4116,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[1993,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two conformers of protonated pyruvate, CH<jats:sub>3<\/jats:sub>C<jats:sup>+<\/jats:sup>(OH)COO, with the OH group either <jats:italic>trans<\/jats:italic> or <jats:italic>cis<\/jats:italic> to the methyl group and the carboxylate group in the C\uf8ffC\uf8ffC plane have been studied using the <jats:italic>ab initio<\/jats:italic> SCF\/3\u201021G method, as well as by some semiempirical AM1 calculations. Both <jats:italic>ab initio<\/jats:italic> SCF and AM1 curves for the potential energy as a function of the C\uf8ffCOO distance exhibit a minimum corresponding to a complex of methylhydroxycarbene, CH<jats:sub>3<\/jats:sub>COH, associated with carbon dioxide, but only the AM1 curves predict an inner minimum corresponding to a covalently bonded protonated pyruvate molecule with a C\uf8ffCOO distance of 1.6\u20131.7 \u00c5. The two models also disagree on the dissociation pathway for pyruvic acid, with the AM1 calculations predicting formation of acetyl and HOCO radicals while the <jats:italic>ab initio<\/jats:italic> method predicts dissociation into methylhydroxycarbene and carbon dioxide following an initial intramolecular proton transfer. The weakly bound complexes of methylhydroxycarbene and carbon dioxide have been studied in some detail using <jats:italic>ab initio<\/jats:italic> SCF and MP2 methods in conjunction with 6\u2010311G** basis sets, obtaining equilibrium geometries and vibrational frequencies. In addition, the lactone\u2010type isomer of protonated pyruvate, which contains a C\uf8ffC\uf8ffO ring, was also studied. The conclusions of these calculations are consistent with those from earlier work using the smaller 3\u201021G basis set. The most stable complex is predicted to occur between <jats:italic>trans<\/jats:italic>\u2010methylhydroxycarbene and carbon dioxide where substantial stabilization is provided by an OH  \u20db OC hydrogen bond. \u00a9 1993 John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/jcc.540140611","type":"journal-article","created":{"date-parts":[[2005,1,2]],"date-time":"2005-01-02T01:01:48Z","timestamp":1104627708000},"page":"699-714","source":"Crossref","is-referenced-by-count":11,"title":["Theoretical study of \u201cprotonated pyruvate\u201d: A methylhydroxycarbene\u2014carbon dioxide complex\u2014implications for the decarboxylation of pyruvic acid"],"prefix":"10.1002","volume":"14","author":[{"given":"Kathryn E.","family":"Norris","sequence":"first","affiliation":[]},{"given":"George B.","family":"Bacskay","sequence":"additional","affiliation":[]},{"given":"Jill E.","family":"Gready","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2004,9,7]]},"reference":[{"key":"e_1_2_1_2_2","author":"Norris K.E.","journal-title":"J. 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