{"id":"https://openalex.org/W2316548484","doi":"https://doi.org/10.1021/ct3000553","title":"Why Cyclooctatetraene Is Highly Stabilized: The Importance of \u201cTwo-Way\u201d (Double) Hyperconjugation","display_name":"Why Cyclooctatetraene Is Highly Stabilized: The Importance of \u201cTwo-Way\u201d (Double) Hyperconjugation","publication_year":2012,"publication_date":"2012-02-28","ids":{"openalex":"https://openalex.org/W2316548484","doi":"https://doi.org/10.1021/ct3000553","mag":"2316548484","pmid":"https://pubmed.ncbi.nlm.nih.gov/26596744"},"language":"en","primary_location":{"id":"doi:10.1021/ct3000553","doi":"https://doi.org/10.1021/ct3000553","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ct3000553","pdf_url":null,"source":{"id":"https://openalex.org/S189701308","display_name":"Journal of Chemical Theory and Computation","issn_l":"1549-9618","issn":["1549-9618","1549-9626"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","jufo-2","ki-jl-2","medline","norway-2","poland-140","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 Chemical Theory and Computation","raw_type":"journal-article"},"volume":null,"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/A5026542113","display_name":"Judy I-Chia Wu","orcid":"https://orcid.org/0000-0003-0590-5290","observed_orcids":["https://orcid.org/0000-0003-0590-5290"]},"institutions":[{"id":"https://openalex.org/I165733156","display_name":"University of Georgia","ror":"https://ror.org/00te3t702","country_code":"US","type":"education","lineage":["https://openalex.org/I165733156"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Judy I. Wu","raw_affiliation_strings":["Department\rof Chemistry, University of Georgia, Athens,\rGeorgia 30602, United\rStates"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Chemistry, University of Georgia, Athens,\rGeorgia 30602, United\rStates","institution_ids":["https://openalex.org/I165733156"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5009883474","display_name":"Israel Fern\u00e1ndez","orcid":"https://orcid.org/0000-0002-0186-9774","observed_orcids":["https://orcid.org/0000-0002-0186-9774"]},"institutions":[{"id":"https://openalex.org/I121748325","display_name":"Universidad Complutense de Madrid","ror":"https://ror.org/02p0gd045","country_code":"ES","type":"education","lineage":["https://openalex.org/I121748325"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Israel Fern\u00e1ndez","raw_affiliation_strings":["Departamento de\rQu\u00edmica\rOrg\u00e1nica, Facultad de Ciencias Qu\u00edmicas, Universidad Complutense Madrid, 28040, Madrid, Spain"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento de\rQu\u00edmica\rOrg\u00e1nica, Facultad de Ciencias Qu\u00edmicas, Universidad Complutense Madrid, 28040, Madrid, Spain","institution_ids":["https://openalex.org/I121748325"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5011717029","display_name":"Yirong Mo","orcid":"https://orcid.org/0000-0002-2994-7754","observed_orcids":["https://orcid.org/0000-0002-2994-7754"]},"institutions":[{"id":"https://openalex.org/I141649380","display_name":"Western Michigan University","ror":"https://ror.org/04j198w64","country_code":"US","type":"education","lineage":["https://openalex.org/I141649380"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Yirong Mo","raw_affiliation_strings":["Department of Chemistry, Western Michigan University, Kalamazoo, Michigan 49008,\rUnited States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Western Michigan University, Kalamazoo, Michigan 49008,\rUnited States","institution_ids":["https://openalex.org/I141649380"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5109987002","display_name":"Paul von Ragu\u00e9 Schleyer","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I165733156","display_name":"University of Georgia","ror":"https://ror.org/00te3t702","country_code":"US","type":"education","lineage":["https://openalex.org/I165733156"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Paul von Ragu\u00e9 Schleyer","raw_affiliation_strings":["Department\rof Chemistry, University of Georgia, Athens,\rGeorgia 30602, United\rStates"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Chemistry, University of Georgia, Athens,\rGeorgia 30602, United\rStates","institution_ids":["https://openalex.org/I165733156"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5109987002"],"corresponding_institution_ids":["https://openalex.org/I165733156"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.5239,"has_fulltext":false,"cited_by_count":58,"citation_normalized_percentile":{"value":0.88946241,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"8","issue":"4","first_page":"1280","last_page":"1287"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.5458999872207642,"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/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.5458999872207642,"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/T10002","display_name":"Advanced Chemical Physics Studies","score":0.35670000314712524,"subfield":{"id":"https://openalex.org/subfields/3107","display_name":"Atomic and Molecular Physics, and Optics"},"field":{"id":"https://openalex.org/fields/31","display_name":"Physics and Astronomy"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.018400000408291817,"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/cyclooctatetraene","display_name":"cyclooctatetraene","score":1.0},{"id":"https://openalex.org/keywords/ring-puckering","display_name":"ring puckering","score":0.8240000009536743},{"id":"https://openalex.org/keywords/pi-conjugation","display_name":"\u03c0-conjugation","score":0.6880000233650208},{"id":"https://openalex.org/keywords/1-3-butadiene","display_name":"1,3-butadiene","score":0.9100000262260437},{"id":"https://openalex.org/keywords/allyl-cations","display_name":"allyl cations","score":0.6990000009536743},{"id":"https://openalex.org/keywords/styrene","display_name":"styrene","score":0.949999988079071},{"id":"https://openalex.org/keywords/biphenyl","display_name":"biphenyl","score":0.9879999756813049},{"id":"https://openalex.org/keywords/ethylene","display_name":"ethylene","score":0.8830000162124634}],"concepts":[{"id":"https://openalex.org/C177186529","wikidata":"https://www.wikidata.org/wiki/Q899217","display_name":"Hyperconjugation","level":3,"score":0.9566423892974854},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7024568915367126},{"id":"https://openalex.org/C144557053","wikidata":"https://www.wikidata.org/wiki/Q498946","display_name":"Isodesmic reaction","level":3,"score":0.5327026844024658},{"id":"https://openalex.org/C2779594873","wikidata":"https://www.wikidata.org/wiki/Q2519471","display_name":"Polyene","level":2,"score":0.5186523795127869},{"id":"https://openalex.org/C2781333609","wikidata":"https://www.wikidata.org/wiki/Q900926","display_name":"Cyclooctatetraene","level":3,"score":0.49769046902656555},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.4726354479789734},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.41293489933013916},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.34719228744506836},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.3411504626274109},{"id":"https://openalex.org/C152365726","wikidata":"https://www.wikidata.org/wiki/Q1048589","display_name":"Density functional theory","level":2,"score":0.22666257619857788},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.14356449246406555},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.09365960955619812}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ct3000553","doi":"https://doi.org/10.1021/ct3000553","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ct3000553","pdf_url":null,"source":{"id":"https://openalex.org/S189701308","display_name":"Journal of Chemical Theory and Computation","issn_l":"1549-9618","issn":["1549-9618","1549-9626"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","jufo-2","ki-jl-2","medline","norway-2","poland-140","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 Chemical Theory and Computation","raw_type":"journal-article"},{"id":"pmid:26596744","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/26596744","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 chemical theory and computation","raw_type":"Journal 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":100,"referenced_works":["https://openalex.org/W563132230","https://openalex.org/W1514369830","https://openalex.org/W1520957603","https://openalex.org/W1575789087","https://openalex.org/W1964144869","https://openalex.org/W1966464252","https://openalex.org/W1972552094","https://openalex.org/W1975160218","https://openalex.org/W1975674209","https://openalex.org/W1977343220","https://openalex.org/W1983103022","https://openalex.org/W1985273378","https://openalex.org/W1985883119","https://openalex.org/W1988809647","https://openalex.org/W1992834851","https://openalex.org/W1993999000","https://openalex.org/W1996403326","https://openalex.org/W1997303632","https://openalex.org/W1998340949","https://openalex.org/W1998648411","https://openalex.org/W1999386585","https://openalex.org/W2002160856","https://openalex.org/W2003885743","https://openalex.org/W2007959319","https://openalex.org/W2013236757","https://openalex.org/W2014586003","https://openalex.org/W2019438068","https://openalex.org/W2019443157","https://openalex.org/W2019542484","https://openalex.org/W2021223924","https://openalex.org/W2022950330","https://openalex.org/W2028281685","https://openalex.org/W2032070236","https://openalex.org/W2032666240","https://openalex.org/W2033638126","https://openalex.org/W2034007959","https://openalex.org/W2036085011","https://openalex.org/W2036203356","https://openalex.org/W2038767330","https://openalex.org/W2041148200","https://openalex.org/W2044931670","https://openalex.org/W2046270023","https://openalex.org/W2046729271","https://openalex.org/W2047233588","https://openalex.org/W2051879335","https://openalex.org/W2053520383","https://openalex.org/W2054679865","https://openalex.org/W2058080684","https://openalex.org/W2059121232","https://openalex.org/W2064932453","https://openalex.org/W2067294874","https://openalex.org/W2069011116","https://openalex.org/W2071040663","https://openalex.org/W2080738440","https://openalex.org/W2081160491","https://openalex.org/W2087698083","https://openalex.org/W2091973812","https://openalex.org/W2093187979","https://openalex.org/W2094541395","https://openalex.org/W2101409933","https://openalex.org/W2103176800","https://openalex.org/W2105116319","https://openalex.org/W2109958925","https://openalex.org/W2110658611","https://openalex.org/W2111702596","https://openalex.org/W2114385796","https://openalex.org/W2120787330","https://openalex.org/W2125487112","https://openalex.org/W2130918438","https://openalex.org/W2136720937","https://openalex.org/W2140976435","https://openalex.org/W2142344372","https://openalex.org/W2147802136","https://openalex.org/W2152116375","https://openalex.org/W2157915887","https://openalex.org/W2162147120","https://openalex.org/W2165669614","https://openalex.org/W2168529586","https://openalex.org/W2168995068","https://openalex.org/W2316597460","https://openalex.org/W2316884554","https://openalex.org/W2317638296","https://openalex.org/W2321168360","https://openalex.org/W2327829200","https://openalex.org/W2328127226","https://openalex.org/W2328441210","https://openalex.org/W2331160533","https://openalex.org/W2331990969","https://openalex.org/W2332041736","https://openalex.org/W2916848576","https://openalex.org/W2950466173","https://openalex.org/W2951876088","https://openalex.org/W2952995430","https://openalex.org/W2984297908","https://openalex.org/W3005413016","https://openalex.org/W4211042738","https://openalex.org/W4232665822","https://openalex.org/W4235998838","https://openalex.org/W4243924813","https://openalex.org/W4249194997"],"related_works":["https://openalex.org/W1966957970","https://openalex.org/W2147802136","https://openalex.org/W2045615189","https://openalex.org/W1988871473","https://openalex.org/W2157221146","https://openalex.org/W2069945669","https://openalex.org/W2746439233","https://openalex.org/W1482496910","https://openalex.org/W2061987895","https://openalex.org/W2079543064"],"abstract_inverted_index":{"Despite":[0],"its":[1,39],"highly":[2],"nonplanar":[3],"geometry,":[4],"the":[5,32,49,56,61,65,74,110,127],"tub-shaped":[6],"D2d":[7,28,113],"cyclooctatetraene":[8],"(COT)":[9],"minimum":[10],"is":[11],"far":[12],"from":[13,48],"being":[14],"an":[15],"unconjugated":[16],"polyene":[17],"model":[18,108],"devoid":[19],"of":[20,27,80,90,112,122],"important":[21],"\u03c0":[22,81,97],"interactions.":[23],"The":[24,117],"warped":[25],"skeleton":[26],"COT":[29],"results":[30],"in":[31],"large":[33],"stabilization":[34],"(41.1":[35],"kcal/mol)":[36],"revealed":[37],"by":[38,137],"isodesmic":[40],"bond":[41,88],"separation":[42],"energy":[43],"(BSE).":[44],"This":[45],"originates":[46],"largely":[47],"\"two-way\"":[50,100,138],"hyperconjugation,":[51],"back":[52],"and":[53,64,99,103,132],"forth":[54],"across":[55],"C-C":[57,86],"single":[58,87],"bonds,":[59],"between":[60,96],"CC/CH":[62],"\u03c3(\u03c3*)":[63],"C\u2550C":[66],"(\u03c0*)\u03c0":[67],"orbitals.":[68],"These":[69],"hyperconjugative":[70],"effects":[71],"compensate":[72],"for":[73,109],"substantial,":[75],"but":[76],"not":[77],"complete,":[78],"loss":[79],"conjugation":[82,98],"upon":[83],"ring":[84],"puckering.":[85],"rotation":[89],"1,3-butadiene":[91],"involves":[92],"a":[93,106],"similar":[94],"interplay":[95],"double":[101],"hyperconjugation":[102],"serves":[104],"as":[105],"simple":[107],"inversion":[111],"to":[114],"D4h":[115],"COT.":[116],"perpendicular":[118],"rotational":[119],"transition":[120],"states":[121],"many":[123],"other":[124],"systems,":[125],"e.g.,":[126],"allyl":[128],"cation,":[129],"styrene,":[130],"biphenyl,":[131],"ethene,":[133],"are":[134],"stabilized":[135],"similarly":[136],"hyperconjugation.":[139]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":4},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":6},{"year":2019,"cited_by_count":6},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":5},{"year":2013,"cited_by_count":6},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
