{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Gomes GDP"],"funding":["Division of Chemistry","Florida State University"],"pagination":["6783-6791"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5508698"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["6(12)"],"pubmed_abstract":["The unusual stability of bis- and tris-peroxides contradicts the conventional wisdom - some of them can melt without decomposition at temperatures exceeding 100 °C. In this work, we disclose a stabilizing stereoelectronic effect that two peroxide groups can exert on each other. This stabilization originates from strong anomeric n<sub>O</sub> → σ*<sub>CO</sub> interactions that are absent in mono-peroxides but reintroduced in molecules where two peroxide moieties are separated by a CH<sub>2</sub> group. Furthermore, such effects can be induced by other σ-acceptors and amplified by structural constraints imposed by cyclic and bicyclic frameworks."],"journal":["Chemical science"],"pubmed_title":["Stereoelectronic source of the anomalous stability of bis-peroxides."],"pmcid":["PMC5508698"],"funding_grant_id":["CHE-1465142"],"pubmed_authors":["Gomes GDP","Terent'ev A","Vil' V","Alabugin IV"],"additional_accession":[]},"is_claimable":false,"name":"Stereoelectronic source of the anomalous stability of bis-peroxides.","description":"The unusual stability of bis- and tris-peroxides contradicts the conventional wisdom - some of them can melt without decomposition at temperatures exceeding 100 °C. In this work, we disclose a stabilizing stereoelectronic effect that two peroxide groups can exert on each other. This stabilization originates from strong anomeric n<sub>O</sub> → σ*<sub>CO</sub> interactions that are absent in mono-peroxides but reintroduced in molecules where two peroxide moieties are separated by a CH<sub>2</sub> group. Furthermore, such effects can be induced by other σ-acceptors and amplified by structural constraints imposed by cyclic and bicyclic frameworks.","dates":{"release":"2015-01-01T00:00:00Z","publication":"2015 Dec","modification":"2025-04-18T20:41:55.268Z","creation":"2019-03-27T02:50:18Z"},"accession":"S-EPMC5508698","cross_references":{"pubmed":["28757970"],"doi":["10.1039/c5sc02402a"]}}