{"id":"https://openalex.org/W2140705674","doi":"https://doi.org/10.1021/ja042590x","title":"The Mechanism of Selective Purine C-Nitration Revealed: NMR Studies Demonstrate Formation and Radical Rearrangement of an N7-Nitramine Intermediate","display_name":"The Mechanism of Selective Purine C-Nitration Revealed: NMR Studies Demonstrate Formation and Radical Rearrangement of an N7-Nitramine Intermediate","publication_year":2005,"publication_date":"2005-03-30","ids":{"openalex":"https://openalex.org/W2140705674","doi":"https://doi.org/10.1021/ja042590x","mag":"2140705674","pmid":"https://pubmed.ncbi.nlm.nih.gov/15839695"},"language":"en","primary_location":{"id":"doi:10.1021/ja042590x","doi":"https://doi.org/10.1021/ja042590x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja042590x","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5016596380","display_name":"Boris Rodenko","orcid":"https://orcid.org/0000-0001-5223-4296","observed_orcids":["https://orcid.org/0000-0001-5223-4296"]},"institutions":[{"id":"https://openalex.org/I887064364","display_name":"University of Amsterdam","ror":"https://ror.org/04dkp9463","country_code":"NL","type":"education","lineage":["https://openalex.org/I887064364"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Boris Rodenko","raw_affiliation_strings":["Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands","institution_ids":["https://openalex.org/I887064364"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5014333882","display_name":"Melle Koch","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I887064364","display_name":"University of Amsterdam","ror":"https://ror.org/04dkp9463","country_code":"NL","type":"education","lineage":["https://openalex.org/I887064364"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Melle Koch","raw_affiliation_strings":["Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands","institution_ids":["https://openalex.org/I887064364"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5088863406","display_name":"Alida M. van der Burg","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I887064364","display_name":"University of Amsterdam","ror":"https://ror.org/04dkp9463","country_code":"NL","type":"education","lineage":["https://openalex.org/I887064364"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Alida M. van der Burg","raw_affiliation_strings":["Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands","institution_ids":["https://openalex.org/I887064364"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110273526","display_name":"Martin J. Wanner","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I887064364","display_name":"University of Amsterdam","ror":"https://ror.org/04dkp9463","country_code":"NL","type":"education","lineage":["https://openalex.org/I887064364"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Martin J. Wanner","raw_affiliation_strings":["Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands","institution_ids":["https://openalex.org/I887064364"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5113619404","display_name":"Gerrit\u2010Jan Koomen","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I887064364","display_name":"University of Amsterdam","ror":"https://ror.org/04dkp9463","country_code":"NL","type":"education","lineage":["https://openalex.org/I887064364"]}],"countries":["NL"],"is_corresponding":false,"raw_author_name":"Gerrit-Jan Koomen","raw_affiliation_strings":["Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Van't Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands","institution_ids":["https://openalex.org/I887064364"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I887064364"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.1436,"has_fulltext":false,"cited_by_count":19,"citation_normalized_percentile":{"value":0.74226911,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":96},"biblio":{"volume":"127","issue":"16","first_page":"5957","last_page":"5963"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.9185000061988831,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.9185000061988831,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T14068","display_name":"Organic and Inorganic Chemical Reactions","score":0.01679999940097332,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12410","display_name":"Structural and Chemical Analysis of Organic and Inorganic Compounds","score":0.012600000016391277,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/radical-rearrangement","display_name":"radical rearrangement","score":0.7879999876022339},{"id":"https://openalex.org/keywords/trifluoroacetic-anhydride","display_name":"trifluoroacetic anhydride","score":0.968999981880188},{"id":"https://openalex.org/keywords/radical-trapping","display_name":"radical trapping","score":0.75},{"id":"https://openalex.org/keywords/intermolecular-rearrangement","display_name":"intermolecular rearrangement","score":0.8640000224113464},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"reaction mechanism","score":0.6230000257492065}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9493460059165955},{"id":"https://openalex.org/C2775856698","wikidata":"https://www.wikidata.org/wiki/Q909607","display_name":"Nitration","level":2,"score":0.8950380086898804},{"id":"https://openalex.org/C2776001701","wikidata":"https://www.wikidata.org/wiki/Q4497712","display_name":"CIDNP","level":3,"score":0.718515157699585},{"id":"https://openalex.org/C2781143453","wikidata":"https://www.wikidata.org/wiki/Q411501","display_name":"Trifluoroacetic anhydride","level":2,"score":0.6602412462234497},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.6080748438835144},{"id":"https://openalex.org/C2776476023","wikidata":"https://www.wikidata.org/wiki/Q188261","display_name":"Purine","level":3,"score":0.515805721282959},{"id":"https://openalex.org/C2776568683","wikidata":"https://www.wikidata.org/wiki/Q23005640","display_name":"Moiety","level":2,"score":0.4219900071620941},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.38622909784317017},{"id":"https://openalex.org/C139066938","wikidata":"https://www.wikidata.org/wiki/Q185056","display_name":"Radical","level":2,"score":0.34166210889816284},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.32376062870025635},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2241707146167755},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0},{"id":"https://openalex.org/C181199279","wikidata":"https://www.wikidata.org/wiki/Q8047","display_name":"Enzyme","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000089","descriptor_name":"Acetic Anhydrides","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000644","descriptor_name":"Quaternary Ammonium Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000814","descriptor_name":"Aniline Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D005463","descriptor_name":"Fluoroacetates","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D009578","descriptor_name":"Nitrobenzenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009587","descriptor_name":"Nitrogen Isotopes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011687","descriptor_name":"Purines","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011687","descriptor_name":"Purines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D014269","descriptor_name":"Trifluoroacetic Acid","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D019906","descriptor_name":"Nuclear Magnetic Resonance, Biomolecular","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1021/ja042590x","doi":"https://doi.org/10.1021/ja042590x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja042590x","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:15839695","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15839695","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"Journal Article"},{"id":"pmh:oai:dare.uva.nl:openaire_cris_publications/a0764eef-bcba-42f9-9344-bdf20f40048d","doi":null,"is_oa":false,"landing_page_url":"https://handle.uba.uva.nl/personal/pure/en/publications/the-mechanism-of-selective-purine-cnitration-revealed-nmr-studies-demonstrate-formation-and-radical-rearrangement-of-an-n7nitramine-intermediate(a0764eef-bcba-42f9-9344-bdf20f40048d).html","pdf_url":null,"source":{"id":"https://openalex.org/S4306400088","display_name":"UvA-DARE (University of Amsterdam)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I887064364","host_organization_name":"University of Amsterdam","host_organization_lineage":["https://openalex.org/I887064364"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Rodenko, B, Koch, M, van der Burg, A M, Wanner, M J & Koomen, G J 2005, 'The Mechanism of Selective Purine C-Nitration Revealed: NMR Studies Demonstrate Formation and Radical Rearrangement of an N7-Nitramine Intermediate', Journal of the American Chemical Society, vol. 127, no. 6, pp. 5957-5963. https://doi.org/10.1021/ja042590x","raw_type":"info:eu-repo/semantics/article"},{"id":"pmh:uvapub:oai:dare.uva.nl:publications/a0764eef-bcba-42f9-9344-bdf20f40048d","doi":null,"is_oa":false,"landing_page_url":"https://dare.uva.nl/personal/pure/en/publications/the-mechanism-of-selective-purine-cnitration-revealed-nmr-studies-demonstrate-formation-and-radical-rearrangement-of-an-n7nitramine-intermediate(a0764eef-bcba-42f9-9344-bdf20f40048d).html","pdf_url":null,"source":{"id":"https://openalex.org/S4306401843","display_name":"Data Archiving and Networked Services (DANS)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1322597698","host_organization_name":"Royal Netherlands Academy of Arts and Sciences","host_organization_lineage":["https://openalex.org/I1322597698"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Journal of the American Chemical Society, 127(6), 5957 - 5963. American Chemical Society","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":25,"referenced_works":["https://openalex.org/W1969780690","https://openalex.org/W1981379848","https://openalex.org/W1997027999","https://openalex.org/W1997075146","https://openalex.org/W2020103318","https://openalex.org/W2020898358","https://openalex.org/W2022394955","https://openalex.org/W2028080850","https://openalex.org/W2031204811","https://openalex.org/W2044005585","https://openalex.org/W2046347327","https://openalex.org/W2046889406","https://openalex.org/W2054565399","https://openalex.org/W2058932549","https://openalex.org/W2062791227","https://openalex.org/W2072918271","https://openalex.org/W2084748387","https://openalex.org/W2113662093","https://openalex.org/W2133436228","https://openalex.org/W2162267657","https://openalex.org/W2320180662","https://openalex.org/W2497268321","https://openalex.org/W2738777669","https://openalex.org/W2952650779","https://openalex.org/W2953079323"],"related_works":["https://openalex.org/W2950784928","https://openalex.org/W2951450883","https://openalex.org/W4394013753","https://openalex.org/W2041569367","https://openalex.org/W1492027705","https://openalex.org/W2095166952","https://openalex.org/W2982948845","https://openalex.org/W2006793116","https://openalex.org/W1987711880","https://openalex.org/W2950320932"],"abstract_inverted_index":{"Modified":[0],"purine":[1,15,27,59,67,121,180],"derivatives":[2],"are":[3,17],"of":[4,35,55,64,95,184,225],"great":[5],"importance":[6],"in":[7,110,125,212],"biomedical":[8],"sciences,":[9],"and":[10,25,38,103,152],"substitution":[11],"reactions":[12],"on":[13,119],"the":[14,58,62,96,120,161,187,196,201,226],"skeleton":[16],"intensively":[18],"studied.":[19],"In":[20],"our":[21],"laboratory,":[22],"an":[23,76,213],"efficient":[24],"selective":[26,66],"C2-nitration":[28,68],"reaction":[29,69,108],"was":[30,101,142,190],"developed":[31],"using":[32,84],"a":[33,48,53,88,111,126,133,165,170],"mixture":[34],"tetrabutylammonium":[36],"nitrate":[37,118],"trifluoroacetic":[39],"anhydride.":[40],"The":[41,182],"resulting":[42],"2-nitro":[43],"moiety":[44],"appeared":[45],"to":[46,51,81,177],"be":[47],"versatile":[49],"handle":[50],"introduce":[52],"variety":[54],"pharmacophores":[56],"onto":[57],"skeleton.":[60],"Since":[61],"mechanism":[63],"this":[65,107],"has":[70],"remained":[71],"unclear,":[72],"we":[73,104],"now":[74],"present":[75],"extensive":[77],"NMR":[78],"study":[79],"leading":[80],"its":[82],"elucidation,":[83],"N9-Boc-protected":[85],"6-chloropurine":[86],"as":[87],"model":[89],"compound.":[90],"Direct":[91],"electrophilic":[92],"aromatic":[93],"nitration":[94],"highly":[97],"electron-deficient":[98],"C2":[99],"position":[100,123],"excluded,":[102],"demonstrate":[105],"that":[106,129,173,207,223],"occurs":[109],"three-step":[112],"process.":[113,215],"Electrophilic":[114],"attack":[115],"by":[116,132,148,193],"trifluoroacetyl":[117],"N7":[122],"results":[124],"nitrammonium":[127],"species":[128,172],"is":[130,209],"trapped":[131],"trifluoroacetate":[134],"anion":[135],"furnishing":[136],"N7-nitramine":[137,162],"intermediate":[138,141,163],"11.":[139],"This":[140],"characterized":[143],"at":[144],"-50":[145],"degrees":[146,159],"C":[147],"(1)H,":[149],"(13)C,":[150],"(15)N,":[151],"(19)F":[153],"NMR.":[154],"At":[155],"T":[156],">":[157],"-40":[158],"C,":[160],"undergoes":[164],"nitramine":[166,188,227],"rearrangement,":[167],"which":[168],"generates":[169],"C2-nitro":[171],"immediately":[174],"eliminates":[175],"TFA":[176],"give":[178],"2-nitro-6-chloro-9-Boc":[179],"10.":[181],"involvement":[183],"radicals":[185],"during":[186],"rearrangement":[189,228],"unequivocally":[191],"established":[192],"(15)N-CIDNP.":[194],"Moreover,":[195],"emission":[197],"signal":[198],"observed":[199],"for":[200],"rearranged":[202],"product,":[203],"2-nitropurine":[204],"10,":[205],"showed":[206],"it":[208],"primarily":[210],"formed":[211],"intermolecular":[214],"A":[216],"quantitative":[217],"radical":[218],"trapping":[219],"experiment":[220],"finally":[221],"disclosed":[222],"65-70%":[224],"takes":[229],"place":[230],"intermolecularly.":[231]},"counts_by_year":[{"year":2022,"cited_by_count":3},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":1},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}