{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Tombari RJ"],"funding":["National Institutes of Health","University of California, Davis","NIH HHS","NIGMS NIH HHS","National Science Foundation"],"pagination":["7575-7580"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8462971"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["19(35)"],"pubmed_abstract":["Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component."],"journal":["Organic & biomolecular chemistry"],"pubmed_title":["Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions."],"pmcid":["PMC8462971"],"funding_grant_id":["R01GM128997","T32GM113770","AggieLight Program","CHE0443516","R01 GM128997","S10 OD025271","R. Bryan Miller Graduate Fellowship","T32 GM113770","Provost’s Undergraduate Fellowship","Francesca Miller Undergraduate Research Award","CHE9808183","1S10OD025271"],"pubmed_authors":["Tantillo DJ","Gingrich PW","Tombari RJ","Olson DE","Tuck JR","Yardeny N"],"additional_accession":[]},"is_claimable":false,"name":"Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions.","description":"Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Sep","modification":"2025-04-22T21:13:41.093Z","creation":"2025-04-06T03:28:20.398Z"},"accession":"S-EPMC8462971","cross_references":{"pubmed":["34524347"],"doi":["10.1039/d1ob01450a"]}}