{"id":"https://openalex.org/W2123013869","doi":"https://doi.org/10.1002/jcc.22954","title":"A stepwise retro\u2010imino\u2010ene as a key step in the mechanism of allene formation via the Crabb\u00e9 acetylene homologation","display_name":"A stepwise retro\u2010imino\u2010ene as a key step in the mechanism of allene formation via the Crabb\u00e9 acetylene homologation","publication_year":2012,"publication_date":"2012-03-04","ids":{"openalex":"https://openalex.org/W2123013869","doi":"https://doi.org/10.1002/jcc.22954","mag":"2123013869","pmid":"https://pubmed.ncbi.nlm.nih.gov/22389177"},"language":"en","primary_location":{"id":"doi:10.1002/jcc.22954","is_oa":false,"landing_page_url":"https://doi.org/10.1002/jcc.22954","pdf_url":null,"source":{"id":"https://openalex.org/S21117631","display_name":"Journal of Computational Chemistry","issn_l":"0192-8651","issn":["0192-8651","1096-987X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Computational Chemistry","raw_type":"journal-article"},"type":"article","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/A5016248308","display_name":"Marta Gonz\u00e1lez Comesa\u00f1a","orcid":"https://orcid.org/0000-0003-2959-4407"},"institutions":[{"id":"https://openalex.org/I6289922","display_name":"Universidade de Vigo","ror":"https://ror.org/05rdf8595","country_code":"ES","type":"education","lineage":["https://openalex.org/I6289922"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Marta Gonz\u00e1lez","raw_affiliation_strings":["Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain"],"affiliations":[{"raw_affiliation_string":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5048399894","display_name":"Roi \u00c1lvarez Rodr\u00edguez","orcid":null},"institutions":[{"id":"https://openalex.org/I6289922","display_name":"Universidade de Vigo","ror":"https://ror.org/05rdf8595","country_code":"ES","type":"education","lineage":["https://openalex.org/I6289922"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Roi \u00c1lvarez Rodr\u00edguez","raw_affiliation_strings":["Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain"],"affiliations":[{"raw_affiliation_string":"Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]},{"raw_affiliation_string":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056005699","display_name":"Mar\u0131\u0301a Magdalena Cid","orcid":"https://orcid.org/0000-0003-1655-5580"},"institutions":[{"id":"https://openalex.org/I6289922","display_name":"Universidade de Vigo","ror":"https://ror.org/05rdf8595","country_code":"ES","type":"education","lineage":["https://openalex.org/I6289922"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Maria Magdalena Cid","raw_affiliation_strings":["Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain"],"affiliations":[{"raw_affiliation_string":"Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]},{"raw_affiliation_string":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5058546077","display_name":"Carlos Silva L\u00f3pez","orcid":"https://orcid.org/0000-0003-4955-9844"},"institutions":[{"id":"https://openalex.org/I6289922","display_name":"Universidade de Vigo","ror":"https://ror.org/05rdf8595","country_code":"ES","type":"education","lineage":["https://openalex.org/I6289922"]}],"countries":["ES"],"is_corresponding":true,"raw_author_name":"Carlos Silva L\u00f3pez","raw_affiliation_strings":["Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain"],"affiliations":[{"raw_affiliation_string":"Departamento de Qui\u0301mica Orga\u0301nica, Facultade de Qui\u0301mica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]},{"raw_affiliation_string":"Departamento de Qu\u00edmica Org\u00e1nica, Facultade de Qu\u00edmica, Universidade de Vigo, Lagoas, Marcosende, Vigo 36310, Spain","institution_ids":["https://openalex.org/I6289922"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5058546077"],"corresponding_institution_ids":["https://openalex.org/I6289922"],"apc_list":{"value":4840,"currency":"USD","value_usd":4840},"apc_paid":null,"fwci":0.2826,"has_fulltext":false,"cited_by_count":6,"citation_normalized_percentile":{"value":0.60714087,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":96},"biblio":{"volume":"33","issue":"13","first_page":"1236","last_page":"1239"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.9987999796867371,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.9987999796867371,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T10947","display_name":"Fluorine in Organic Chemistry","score":0.9984999895095825,"subfield":{"id":"https://openalex.org/subfields/3003","display_name":"Pharmaceutical Science"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10911","display_name":"Chemical Synthesis and Analysis","score":0.9976000189781189,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/acetylene","display_name":"Acetylene","score":0.8640124797821045},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.7988450527191162},{"id":"https://openalex.org/keywords/allene","display_name":"Allene","score":0.7338348031044006},{"id":"https://openalex.org/keywords/kinetic-isotope-effect","display_name":"Kinetic isotope effect","score":0.6466759443283081},{"id":"https://openalex.org/keywords/mechanism","display_name":"Mechanism (biology)","score":0.6364250183105469},{"id":"https://openalex.org/keywords/intramolecular-force","display_name":"Intramolecular force","score":0.5785514116287231},{"id":"https://openalex.org/keywords/concerted-reaction","display_name":"Concerted reaction","score":0.4781821072101593},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"Reaction mechanism","score":0.4302457571029663},{"id":"https://openalex.org/keywords/ene-reaction","display_name":"Ene reaction","score":0.4159132242202759},{"id":"https://openalex.org/keywords/photochemistry","display_name":"Photochemistry","score":0.4064241051673889},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"Computational chemistry","score":0.3845202624797821},{"id":"https://openalex.org/keywords/catalysis","display_name":"Catalysis","score":0.3687286376953125},{"id":"https://openalex.org/keywords/medicinal-chemistry","display_name":"Medicinal chemistry","score":0.3174270987510681},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"Stereochemistry","score":0.25524288415908813},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.19081604480743408},{"id":"https://openalex.org/keywords/deuterium","display_name":"Deuterium","score":0.1512933373451233},{"id":"https://openalex.org/keywords/philosophy","display_name":"Philosophy","score":0.13346317410469055},{"id":"https://openalex.org/keywords/physics","display_name":"Physics","score":0.051634401082992554}],"concepts":[{"id":"https://openalex.org/C2777517455","wikidata":"https://www.wikidata.org/wiki/Q133145","display_name":"Acetylene","level":2,"score":0.8640124797821045},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7988450527191162},{"id":"https://openalex.org/C2778652500","wikidata":"https://www.wikidata.org/wiki/Q411369","display_name":"Allene","level":3,"score":0.7338348031044006},{"id":"https://openalex.org/C69928629","wikidata":"https://www.wikidata.org/wiki/Q1386472","display_name":"Kinetic isotope effect","level":3,"score":0.6466759443283081},{"id":"https://openalex.org/C89611455","wikidata":"https://www.wikidata.org/wiki/Q6804646","display_name":"Mechanism (biology)","level":2,"score":0.6364250183105469},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.5785514116287231},{"id":"https://openalex.org/C29135686","wikidata":"https://www.wikidata.org/wiki/Q2733609","display_name":"Concerted reaction","level":3,"score":0.4781821072101593},{"id":"https://openalex.org/C65024703","wikidata":"https://www.wikidata.org/wiki/Q373406","display_name":"Reaction mechanism","level":3,"score":0.4302457571029663},{"id":"https://openalex.org/C27777614","wikidata":"https://www.wikidata.org/wiki/Q26469","display_name":"Ene reaction","level":2,"score":0.4159132242202759},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.4064241051673889},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3845202624797821},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.3687286376953125},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3174270987510681},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.25524288415908813},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.19081604480743408},{"id":"https://openalex.org/C58364064","wikidata":"https://www.wikidata.org/wiki/Q102296","display_name":"Deuterium","level":2,"score":0.1512933373451233},{"id":"https://openalex.org/C138885662","wikidata":"https://www.wikidata.org/wiki/Q5891","display_name":"Philosophy","level":0,"score":0.13346317410469055},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.051634401082992554},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0},{"id":"https://openalex.org/C111472728","wikidata":"https://www.wikidata.org/wiki/Q9471","display_name":"Epistemology","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000114","descriptor_name":"Acetylene","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000114","descriptor_name":"Acetylene","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000114","descriptor_name":"Acetylene","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D000466","descriptor_name":"Alkadienes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003300","descriptor_name":"Copper","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D003300","descriptor_name":"Copper","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D003300","descriptor_name":"Copper","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007700","descriptor_name":"Kinetics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007700","descriptor_name":"Kinetics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007700","descriptor_name":"Kinetics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1002/jcc.22954","is_oa":false,"landing_page_url":"https://doi.org/10.1002/jcc.22954","pdf_url":null,"source":{"id":"https://openalex.org/S21117631","display_name":"Journal of Computational Chemistry","issn_l":"0192-8651","issn":["0192-8651","1096-987X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Computational Chemistry","raw_type":"journal-article"},{"id":"pmid:22389177","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/22389177","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,"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 computational chemistry","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Clean water and sanitation","id":"https://metadata.un.org/sdg/6","score":0.4399999976158142}],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":44,"referenced_works":["https://openalex.org/W194657","https://openalex.org/W652900620","https://openalex.org/W1963737263","https://openalex.org/W1968162933","https://openalex.org/W1968463972","https://openalex.org/W1968831783","https://openalex.org/W1977347044","https://openalex.org/W1977372630","https://openalex.org/W1977616520","https://openalex.org/W1978263407","https://openalex.org/W1981872991","https://openalex.org/W1983129740","https://openalex.org/W1986118507","https://openalex.org/W1995498258","https://openalex.org/W2000306500","https://openalex.org/W2011979358","https://openalex.org/W2013652118","https://openalex.org/W2021824899","https://openalex.org/W2030971064","https://openalex.org/W2033571321","https://openalex.org/W2046424037","https://openalex.org/W2051758552","https://openalex.org/W2068599812","https://openalex.org/W2068952283","https://openalex.org/W2071695492","https://openalex.org/W2072243864","https://openalex.org/W2078073960","https://openalex.org/W2079093476","https://openalex.org/W2085336624","https://openalex.org/W2097500559","https://openalex.org/W2113396627","https://openalex.org/W2124716867","https://openalex.org/W2129975392","https://openalex.org/W2131023386","https://openalex.org/W2135038247","https://openalex.org/W2140889506","https://openalex.org/W2150697053","https://openalex.org/W2158928802","https://openalex.org/W2949367291","https://openalex.org/W2949955268","https://openalex.org/W2949962382","https://openalex.org/W2950024730","https://openalex.org/W2951263840","https://openalex.org/W2953053309"],"related_works":["https://openalex.org/W2028127099","https://openalex.org/W2336739578","https://openalex.org/W2536533957","https://openalex.org/W2588272188","https://openalex.org/W2315078173","https://openalex.org/W2138798760","https://openalex.org/W2022396800","https://openalex.org/W2951495268","https://openalex.org/W2061191738","https://openalex.org/W2074215134"],"abstract_inverted_index":{"The":[0],"mechanism":[1,61],"of":[2,34,45,65],"the":[3,31,35,51,63,76],"acetylene":[4],"homologation":[5],"procedure":[6],"accidentally":[7],"discovered":[8],"and":[9,14,71],"further":[10],"developed":[11],"by":[12],"Crabb\u00e9":[13],"coworkers":[15],"is":[16,30,72],"unknown.":[17],"Kinetic":[18],"isotope":[19],"effect":[20],"(KIE)":[21],"experiments,":[22],"however,":[23],"suggest":[24],"that":[25,50],"an":[26,55],"intramolecular":[27],"hydrogen":[28],"shift":[29],"key":[32],"step":[33],"transformation.":[36],"In":[37],"this":[38,46],"work,":[39],"we":[40],"present":[41],"a":[42,68],"computational":[43],"study":[44],"mechanism.":[47],"We":[48],"found":[49],"reaction":[52,69],"proceeds":[53],"via":[54],"unexpected":[56],"stepwise":[57],"retro-imino-ene":[58],"rearrangement.":[59],"This":[60],"justifies":[62],"role":[64],"Cu(I)":[66],"as":[67],"catalyst":[70],"also":[73],"compatible":[74],"with":[75],"KIE":[77],"experiments":[78],"reported.":[79]},"counts_by_year":[{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":2},{"year":2017,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":1}],"updated_date":"2026-01-13T01:12:25.745995","created_date":"2025-10-10T00:00:00"}