{"doi":"10.1002/oms.1210020507","title":"Fragmentation of some even‐electron nitroaromatic ions: The question of the nitrotropylium ion","abstract":"<jats:title>Abstract</jats:title><jats:p>The behavior of the even‐electron mass 150 ions, (presumably nitrobenzoyl cations) generated by simple α‐cleavage of <jats:italic>m</jats:italic>‐ and <jats:italic>p</jats:italic>‐nitrobenzoic acid derivatives, undergo two competing secondary fragmentations to yield odd‐electron ions by the expulsion of NO and NO<jats:sub>2</jats:sub>. Expulsion of NO from the mass 150 ions from <jats:italic>p</jats:italic>‐nitro compounds is far greater than expulsion of NO from those generated from <jats:italic>m</jats:italic>‐nitro compounds. In addition, the behavior of the even‐electron mass 136 ions, generated from <jats:italic>m</jats:italic>‐ and <jats:italic>p</jats:italic>‐nitrobenzyl compounds, was compared to that of the mass 150 ions and they were found to decompose in a similar fashion. From our results we conclude that the decomposing mass 136 ions produced from either the <jats:italic>m</jats:italic>‐ or <jats:italic>p</jats:italic>‐nitrobenzyl compounds, or both, do not have the nitropylium structure; our data are more consistent with the decomposing ions having nitrobenzyl structures.</jats:p>","journal":"Organic Mass Spectrometry","year":1969,"id":588237,"datarank":1.9988194242639636,"base_score":3.2188758248682006,"endowment":3.2188758248682006,"self_citation_contribution":0.48283137373023016,"citation_network_contribution":1.5159880505337335,"self_endowment_contribution":0.48283137373023016,"citer_contribution":1.5159880505337335,"corpus_percentile":null,"corpus_rank":null,"citation_count":24,"citer_count":22,"citers_with_citation_signal":18,"citers_with_endowment":18,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1504854,"name":"James W. Serum","orcid":null,"position":1,"is_corresponding":false},{"id":190991,"name":"Robert H. Shapiro","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Fragmentation of some even‐electron nitroaromatic ions: The question of the nitrotropylium ion","abstract":"<jats:title>Abstract</jats:title><jats:p>The behavior of the even‐electron mass 150 ions, (presumably nitrobenzoyl cations) generated by simple α‐cleavage of <jats:italic>m</jats:italic>‐ and <jats:italic>p</jats:italic>‐nitrobenzoic acid derivatives, undergo two competing secondary fragmentations to yield odd‐electron ions by the expulsion of NO and NO<jats:sub>2</jats:sub>. Expulsion of NO from the mass 150 ions from <jats:italic>p</jats:italic>‐nitro compounds is far greater than expulsion of NO from those generated from <jats:italic>m</jats:italic>‐nitro compounds. In addition, the behavior of the even‐electron mass 136 ions, generated from <jats:italic>m</jats:italic>‐ and <jats:italic>p</jats:italic>‐nitrobenzyl compounds, was compared to that of the mass 150 ions and they were found to decompose in a similar fashion. From our results we conclude that the decomposing mass 136 ions produced from either the <jats:italic>m</jats:italic>‐ or <jats:italic>p</jats:italic>‐nitrobenzyl compounds, or both, do not have the nitropylium structure; our data are more consistent with the decomposing ions having nitrobenzyl structures.</jats:p>","is_dataset_classified":null,"base_score":3.2188758248682006,"endowment":3.2188758248682006,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"26657633","pmcid":null,"openalex_id":"https://openalex.org/W2009531498","authors":[],"funders":[],"total_grants":0,"fwci":3.9134,"citation_percentile":0.94783033,"influential_citations":0,"citation_trend":[{"year":2022,"count":1},{"year":2024,"count":1}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Foms.1210020507","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/oms.1210020507","host_type":"publisher"},{"url":"https://doi.org/10.1002/oms.1210020507","host_type":"journal"}],"fields_of_study":["Molecular Sensors and Ion Detection","Chemical Reaction Mechanisms","Mass Spectrometry Techniques and Applications"],"mesh_terms":[],"keywords":["Fragmentation (computing)","Ion","Chemistry","Nitro","Yield (engineering)","Electron ionization","Mass spectrum","Electron","Cleavage (geology)","Mass spectrometry","Medicinal chemistry","Analytical Chemistry (journal)","Organic chemistry","Materials science","Physics","Chromatography","Ionization"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-07-19T21:19:58.256078Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}