{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Vaidya SD"],"funding":["National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["6760-6768"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9799075"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["87(10)"],"pubmed_abstract":["Diarylamines possess two potentially atropisomeric C-N axes; however, there are few examples of atropisomerically stable diarylamines in the literature, as the contiguous axes can allow for low energy racemization pathways via concerted bond rotations. Herein, we describe highly atropisomerically stable diarylamines that possess barriers to racemization of 30-36 kcal/mol, corresponding to half-lives to racemization on the decade to century time scale at room temperature. Investigation of the factors that led to the high stereochemical stability suggests that increased conjugation of the aniline lone pair of electrons into a more electron-deficient aryl ring, coupled with intramolecular hydrogen-bonding, locked the corresponding axis into a defined planar conformation, disfavoring the lower"],"journal":["The Journal of organic chemistry"],"pubmed_title":["Approaches toward Atropisomerically Stable and Conformationally Pure Diarylamines."],"pmcid":["PMC9799075"],"funding_grant_id":["R35GM124637","R35 GM124637"],"pubmed_authors":["Heydari BS","Gustafson JL","Toenjes ST","Vaidya SD"],"additional_accession":[]},"is_claimable":false,"name":"Approaches toward Atropisomerically Stable and Conformationally Pure Diarylamines.","description":"Diarylamines possess two potentially atropisomeric C-N axes; however, there are few examples of atropisomerically stable diarylamines in the literature, as the contiguous axes can allow for low energy racemization pathways via concerted bond rotations. Herein, we describe highly atropisomerically stable diarylamines that possess barriers to racemization of 30-36 kcal/mol, corresponding to half-lives to racemization on the decade to century time scale at room temperature. Investigation of the factors that led to the high stereochemical stability suggests that increased conjugation of the aniline lone pair of electrons into a more electron-deficient aryl ring, coupled with intramolecular hydrogen-bonding, locked the corresponding axis into a defined planar conformation, disfavoring the lower","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 May","modification":"2025-05-29T16:23:10.778Z","creation":"2025-05-29T16:23:10.778Z"},"accession":"S-EPMC9799075","cross_references":{"pubmed":["35486501"],"doi":["10.1021/acs.joc.2c00451"]}}