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The results demonstrate that the sodium adducts of the title compounds undergo two competitive fragmentation pathways, and the fragmentation patterns are heavily dependent on the various substituent patterns at the phenolic group. An electron\u2010withdrawing substituent at the <jats:italic>ortho<\/jats:italic>\u2010position always results in the removal of a corresponding phenol analogue, while cleavage by spiroring opening becomes the predominant fragmentation pathway if an electron\u2010donating substituent is at the phenolic group. The substituent effects on the competitive fragmentation pathways were further elucidated by theoretical calculations, single crystal structure analysis, and high\u2010resolution mass spectrometry. The results contribute to the understanding of the gas\u2010phase fragmentation reactions and the structure identification of spirophosphorane analogues by electrospray ionization multistage mass spectrometry.<\/jats:p>","DOI":"10.1002\/jms.4064","type":"journal-article","created":{"date-parts":[[2018,1,16]],"date-time":"2018-01-16T05:46:57Z","timestamp":1516081617000},"page":"314-322","source":"Crossref","is-referenced-by-count":3,"title":["The investigation of substituent effects on the fragmentation pathways of pentacoordinated phenoxyspirophosphoranes by <scp>ESI\u2010MS<sup>n<\/sup><\/scp>"],"prefix":"10.1002","volume":"53","author":[{"given":"Xiaoyan","family":"Cui","sequence":"first","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Can","family":"Sun","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pei","family":"Zhao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yanyan","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1214-5525","authenticated-orcid":false,"given":"Yanchun","family":"Guo","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yufen","family":"Zhao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"},{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry Tsinghua University  Beijing 100084 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4325-5527","authenticated-orcid":false,"given":"Shuxia","family":"Cao","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Engineering, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province Zhengzhou University  Zhengzhou 450052 China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,2,21]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/29.9.1815"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar050188x"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-005-0207-8"},{"key":"e_1_2_6_5_1","first-page":"4642","article-title":"(3S,8S)\u20103,8\u2010Diisopropyl\u20101,6\u2010dioxa\u20104,9\u2010diaza\u20105\u03bb5\u2010phosphaspiro[4.4]nonane\u20102,7\u2010dione","volume":"62","author":"Cao SX","year":"2006","journal-title":"Acta Crystallogr"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.09.056"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5NP00073D"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/jms.472"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/jms.3471"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/jms.432"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/jms.1900"},{"volume-title":"Gaussian 09; 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