{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:53:30Z","timestamp":1786978410542,"version":"build-2736575974"},"reference-count":12,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2010,9,14]],"date-time":"2010-09-14T00:00:00Z","timestamp":1284422400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2010,10,15]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    <jats:italic>N<\/jats:italic>\n                    \u2010Oxides are known to undergo three main thermal degradation reactions, namely deoxygenation, Cope elimination (for\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxides containing a \u03b2\u2010hydrogen) and Meisenheimer rearrangement, in atmospheric pressure chemical ionization mass spectrometry (APCI\u2010MS). The ions corresponding to these thermal degradants observed in the ensuing APCI mass spectra have been used to identify\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxides as well as to determine the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxidation site when the analyte contains multiple tertiary amine groups. In this paper, we report a thermally induced oxygen migration from one\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxide amine to another\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010amine group present in the same molecule through a six\u2010membered ring transition state during APCI\u2010MS analysis. The observed intramolecular oxygen migration resulted in the formation of a new isomeric\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxide, rendering the results of the APCI\u2010MS analysis more difficult to interpret and potentially misleading. In addition, we observed novel degradation behavior that happened after the Meisenheimer rearrangement of the newly formed\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxide: a homolytic cleavage of the N\uf8ffO bond instead of elimination of an aldehyde or a ketone that usually follows the rearrangement. Understanding of these unusual degradation pathways, which have not been reported previously, should facilitate structural elucidation of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxides using APCI\u2010MS analysis. Copyright \u00a9 2010 John Wiley &amp; Sons, Ltd.\n                  <\/jats:p>","DOI":"10.1002\/rcm.4706","type":"journal-article","created":{"date-parts":[[2010,9,15]],"date-time":"2010-09-15T07:31:45Z","timestamp":1284535905000},"page":"2805-2811","source":"Crossref","is-referenced-by-count":7,"title":["Thermally induced intramolecular oxygen migration of\n                    <i>N<\/i>\n                    \u2010oxides in atmospheric pressure chemical ionization mass spectrometry"],"prefix":"10.1002","volume":"24","author":[{"given":"Xin","family":"Wang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abu M.","family":"Rustum","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,9,14]]},"reference":[{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471218812"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.3109\/03602538809049617"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac9911692"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac048203j"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01180a014"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19190520830"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.475"},{"key":"e_1_2_7_9_2","first-page":"92","volume":"7","author":"Norwood DL","year":"2004","journal-title":"Am. 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