{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T12:57:35Z","timestamp":1792155455766,"version":"4.4.0"},"reference-count":20,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2007,12,4]],"date-time":"2007-12-04T00:00:00Z","timestamp":1196726400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Mass Spectrom."],"published-print":{"date-parts":[[2008,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Arylsulfonamides are attractive pharmacophores for drug candidates. Fragmentation behaviors of selected aromatic sulfonamides were investigated using electrospray ionization mass spectrometry in the positive ion mode. Some of the sulfonamides afforded unique loss of 64 (loss of SO<jats:sub>2<\/jats:sub>) ions upon collision\u2010induced dissociation followed by intramolecular rearrangements in the gas phase. This SO<jats:sub>2<\/jats:sub> elimination\u2010rearrangement pathway leading to the generation of [M + H \u2212 SO<jats:sub>2<\/jats:sub>]<jats:sup>+<\/jats:sup> ions appeared to be susceptible to substitutions on the aromatic (Ar) ring that would affect the Ar\uf8ffsulfur bond strength and the stability of the partially positive charge developed at the <jats:italic>ipso<\/jats:italic> position upon bond dissociation. Electron withdrawing groups such as chlorine attached to the aromatic ring at <jats:italic>ortho<\/jats:italic> position seem to promote the SO<jats:sub>2<\/jats:sub> extrusion. Although this fragmentation pathway in atmospheric pressure ionization MS is less predictable than in electron impact MS, it is a frequently encountered reaction. The absence of this fragmentation pathway in some of the arylsulfonamides indicates that other factors such as nucleophilicity of the nitrogen may also play a role in the process. With respect to the site of attachment of the migrating NR\u2032R\u2033, <jats:italic>ipso<\/jats:italic>\u2010substitution on the aromatic ring is evident since this fragmentation mechanism is operative in the fully <jats:italic>ortho<\/jats:italic>\u2010substituted arylsulfonamides. Copyright \u00a9 2007 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/jms.1335","type":"journal-article","created":{"date-parts":[[2007,12,4]],"date-time":"2007-12-04T11:46:27Z","timestamp":1196768787000},"page":"383-393","source":"Crossref","is-referenced-by-count":71,"title":["Fragmentation of aromatic sulfonamides in electrospray ionization mass spectrometry: elimination of SO<sub>2<\/sub> via rearrangement"],"prefix":"10.1002","volume":"43","author":[{"given":"Mingjiang","family":"Sun","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenning","family":"Dai","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David Q.","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,12,4]]},"reference":[{"key":"e_1_2_5_2_2","first-page":"711","article-title":"Mechanism of excretion of sulfonamides in bovine milk","volume":"41","author":"Sisodia CS","year":"1964","journal-title":"Indian Veterinary Journal"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo034643j"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0731-7085(98)00267-2"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.877"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19851180108"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(02)01380-6"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0231(19970615)11:9<1043::AID-RCM945>3.0.CO;2-U"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/oms.1210040118"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac50003a030"},{"key":"e_1_2_5_11_2","first-page":"415","article-title":"Electron impact and field desorption mass spectrometry of 2,4\u2010diamino\u20106\u2010substituted quinazoline sulfonamides","volume":"19","author":"Tang BS","year":"1984","journal-title":"YaoXueXueBao"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.1968"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.2634"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(02)00329-1"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(02)01341-9"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/oms.1210020610"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/oms.1210280708"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19670791102"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.1743"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00972a026"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19790620215"}],"container-title":["Journal of Mass Spectrometry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjms.1335","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jms.1335","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T17:21:11Z","timestamp":1760635271000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jms.1335"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,12,4]]},"references-count":20,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2008,3]]}},"alternative-id":["10.1002\/jms.1335"],"URL":"https:\/\/doi.org\/10.1002\/jms.1335","archive":["Portico"],"relation":{},"ISSN":["1076-5174","1096-9888"],"issn-type":[{"value":"1076-5174","type":"print"},{"value":"1096-9888","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,12,4]]}}}