{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T17:10:39Z","timestamp":1790615439545,"version":"4.1.0"},"reference-count":27,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2005,12,13]],"date-time":"2005-12-13T00:00:00Z","timestamp":1134432000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPhysChem"],"published-print":{"date-parts":[[2006,1,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>The role that silica surface could have played in prebiotic chemistry as a catalyst for peptide bond formation has been addressed at the B3LYP\/6\u201031+G(d,p) level for a model reaction involving glycine and ammonia on a silica cluster mimicking an isolated terminal silanol group present at the silica surface. Hydrogen\u2010bond complexation between glycine and the silanol is followed by the formation of the mixed surface anhydride Si<jats:sub>surf<\/jats:sub>\uf8ffO\uf8ffC(\uf8feO)\uf8ffR, which has been suggested in the literature to activate the C\uf8feO bond towards nucleophilic attack by a second glycine molecule, here simulated by the simpler NH<jats:sub>3<\/jats:sub> molecule. However, B3LYP\/6\u201031+G(d,p) calculations show that formation of the surface mixed anhydride Si<jats:sub>surf<\/jats:sub>\uf8ffO\uf8ffC(\uf8feO)\uf8ffR is disfavoured (\u0394<jats:sub>r<\/jats:sub><\/jats:italic>G<jats:sub><jats:italic>298<\/jats:italic><\/jats:sub><jats:italic>\u22486 kcal mol<\/jats:italic><jats:sup><jats:italic>\u22121<\/jats:italic><\/jats:sup><jats:italic>), and that the surface bond only moderately lowers the free\u2010energy barrier of the nucleophilic attack responsible for peptide bond formation (\u0394<\/jats:italic>G<jats:styled-content>${{{{\\ne}\\hfill \\atop 298\\hfill}}}$<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-ueqn-1.gif\" xlink:title=\"equation image\"\/><\/jats:styled-content><jats:italic>\u224848 kcal\u2009mol<\/jats:italic><jats:sup><jats:italic>\u22121<\/jats:italic><\/jats:sup><jats:italic>) in comparison with the uncatalysed reaction (\u0394<\/jats:italic>G<jats:styled-content>${{{{\\ne}\\hfill \\atop 298\\hfill}}}$<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-ueqn-2.gif\" xlink:title=\"equation image\"\/><\/jats:styled-content><jats:italic>\u224852 kcal\u2009mol<\/jats:italic><jats:sup><jats:italic>\u22121<\/jats:italic><\/jats:sup><jats:italic>). A further decrease of the free\u2010energy barrier of peptide bond formation (\u0394<\/jats:italic>G<jats:styled-content>${{{{\\ne}\\hfill \\atop 298\\hfill}}}$<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-ueqn-3.gif\" xlink:title=\"equation image\"\/><\/jats:styled-content><jats:italic>\u224841 kcal\u2009mol<\/jats:italic><jats:sup><jats:italic>\u22121<\/jats:italic><\/jats:sup><jats:italic>) is achieved by a single water molecule close to the reaction centre acting as a proton\u2010transfer helper in the activated complex. A possible role of strained silica surface defects on the formation of the surface mixed anhydride Si<jats:sub>surf<\/jats:sub>\uf8ffO\uf8ffC(\uf8feO)\uf8ffR has also been addressed.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cphc.200500401","type":"journal-article","created":{"date-parts":[[2005,12,13]],"date-time":"2005-12-13T06:46:50Z","timestamp":1134456410000},"page":"157-163","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":81,"title":["Does Silica Surface Catalyse Peptide Bond Formation? 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