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Additionally, the computed vertical ionization potential for s, trimethylamine, and dimethyl ether, leading to the conclusion that there is no advantage to hydrogen abstraction from trisubstituted hydroxylamines over the corresponding tertiary amines and ethers. Additionally, the computed vertical ionization potential for N,N,O-trimethylhydroxylamine is greater than that for either trimethylamine or dimethyl ether. Together with the established N\u2013O BDEs of \u223c50 kcal.mol\u20131, these findings argue strongly against common notions of trisubstituted hydroxylamines as inherently chemically or metabolically unstable and refute their designation as red flags or structural alerts in drug discovery campaigns. Subsequent to hydrogen abstraction \u03b1- to either nitrogen or oxygen, hydroxylamines undergo facile exothermic N\u2013O bond cleavage to give either O- or N-centered radicals. It is this radical-induced cleavage of hydroxylamines that synthetic chemists exploit for N- and O-centered radical generation rather than any perceived weakness of the N\u2013O bond in the unactivated hydroxylamines themselves.<\/jats:p>","DOI":"10.1021\/acsphyschemau.6c00075","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T15:02:46Z","timestamp":1786201366000},"page":"1244-1251","source":"Crossref","is-referenced-by-count":2,"title":["Energetics\nof Formation and Fragmentation of Carbon-Centered\nRadicals \u03b1- to Nitrogen and Oxygen in\n                    <i>N<\/i>\n                    ,\n                    <i>N<\/i>\n                    ,\n                    <i>O<\/i>\n                    -Trimethylhydroxylamine in Comparison\nto Trimethylamine and Dimethyl Ether: Implications for Medicinal and\nSynthetic Chemistry"],"prefix":"10.1021","volume":"6","author":[{"given":"R. Houston","family":"Givhan","sequence":"first","affiliation":[{"name":"University of Georgia , , 302 East Campus Road , , ,","place":["Athens, Georgia, United States, 30602"]},{"name":"University of Georgia , , 1004 Cedar Street , , ,","place":["Athens, Georgia, United States, 30602"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0252-2083","authenticated-orcid":true,"suffix":"III","given":"Henry F.","family":"Schaefer","sequence":"additional","affiliation":[{"name":"University of Georgia , , 302 East Campus Road , , ,","place":["Athens, Georgia, United States, 30602"]},{"name":"University of Georgia , , 1004 Cedar Street , , ,","place":["Athens, Georgia, United States, 30602"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2400-0083","authenticated-orcid":true,"given":"David","family":"Crich","sequence":"additional","affiliation":[{"name":"University of Georgia , , 302 East Campus Road , , ,","place":["Athens, Georgia, United States, 30602"]},{"name":"University of Georgia , , 250 West Green Street , , ,","place":["Athens, Georgia, United States, 30602"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,8]]},"reference":[{"key":"2026092310074486400_cit1","first-page":"1064","volume-title":"The Chemistry of Hydroxylamines,\nOximes, and Hydroxamic Acids","author":"Rappoport","year":"2009"},{"key":"2026092310074486400_cit2","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/bs.alkal.2025.01.001","article-title":"Hydroxylamine\nNatural Products","volume-title":"The Alkaloids: Chemistry\nand Biology","author":"Bates","year":"2025"},{"key":"2026092310074486400_cit3","doi-asserted-by":"publisher","first-page":"1146","DOI":"10.1002\/ajoc.201700142","article-title":"Securinega Alkaloids: Complex Structures,\nPotent Bioactivites,\nand Efficient Total Syntheses","volume":"6","author":"Wehlauch","year":"2017","journal-title":"Asian J. 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Chem.\nPhys."},{"key":"2026092310074486400_cit88","doi-asserted-by":"publisher","first-page":"054101","DOI":"10.1063\/1.1950567","article-title":"Coupled-Cluster Methods\nIncluding Noniterative Corrections for Quadruple Excitations","volume":"123","author":"Bomble","year":"2005","journal-title":"J. Chem. Phys."},{"key":"2026092310074486400_cit89","doi-asserted-by":"publisher","first-page":"074107","DOI":"10.1063\/1.5142048","article-title":"The MRCC Program\nSystem: Accurate\nQuantum Chemistry from Water to Proteins","volume":"152","author":"Ka\u0301llay","year":"2020","journal-title":"J.\nChem. Phys."},{"key":"2026092310074486400_cit90","unstructured":"Ka\u0301llay, M.; Nagy, P. R.; Mester, D.; Rolik, Z.; Samu, G.; Csontos, J.; Cso\u0301ka, J.; Szabo\u0301, P. B.; Gyevi-Nagy, L.; He\u0301gely, B.; Ladja\u0301nszki, I.; Szegedy, L.; Lado\u0301czki, B.; Petrov, K.; Farkas, M.; Mezei, P. D.; Ganyecz, A.\n          MRCC, A Quantum Chemical Program\nSuite. 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