{"id":"https://openalex.org/W2058719927","doi":"https://doi.org/10.1021/ja9601494","title":"Density Functional Theory Prediction of the Relative Energies and Isotope Effects for the Concerted and Stepwise Mechanisms of the Diels\u2212Alder Reaction of Butadiene and Ethylene","display_name":"Density Functional Theory Prediction of the Relative Energies and Isotope Effects for the Concerted and Stepwise Mechanisms of the Diels\u2212Alder Reaction of Butadiene and Ethylene","publication_year":1996,"publication_date":"1996-01-01","ids":{"openalex":"https://openalex.org/W2058719927","doi":"https://doi.org/10.1021/ja9601494","mag":"2058719927"},"language":"en","primary_location":{"id":"doi:10.1021/ja9601494","doi":"https://doi.org/10.1021/ja9601494","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9601494","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"},"parent_works":[],"lineage":["https://openalex.org/W2058719927"],"child_works_count":0,"type":"article","is_traditional":true,"indexed_in":["crossref"],"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/A5048861360","display_name":"Elisheva Goldstein","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]},{"id":"https://openalex.org/I98947143","display_name":"California State Polytechnic University","ror":"https://ror.org/05by5hm18","country_code":"US","type":"education","lineage":["https://openalex.org/I98947143"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"E. Goldstein","raw_affiliation_strings":["Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768","institution_ids":["https://openalex.org/I161318765","https://openalex.org/I98947143"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5061926860","display_name":"Brett R. Beno","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]},{"id":"https://openalex.org/I98947143","display_name":"California State Polytechnic University","ror":"https://ror.org/05by5hm18","country_code":"US","type":"education","lineage":["https://openalex.org/I98947143"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Brett Beno","raw_affiliation_strings":["Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768","institution_ids":["https://openalex.org/I161318765","https://openalex.org/I98947143"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5042178740","display_name":"Kendall N. Houk","orcid":"https://orcid.org/0000-0002-8387-5261","observed_orcids":["https://orcid.org/0000-0002-8387-5261"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]},{"id":"https://openalex.org/I98947143","display_name":"California State Polytechnic University","ror":"https://ror.org/05by5hm18","country_code":"US","type":"education","lineage":["https://openalex.org/I98947143"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"K. N. Houk","raw_affiliation_strings":["Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, and Department of Chemistry, California State Polytechnic University, Pomona, 3801 West Temple Avenue, Pomona, California 91768","institution_ids":["https://openalex.org/I161318765","https://openalex.org/I98947143"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":24.7408,"has_fulltext":false,"cited_by_count":506,"citation_normalized_percentile":{"value":0.99931175,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":98,"max":100},"biblio":{"volume":"118","issue":"25","first_page":"6036","last_page":"6043"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.9390000104904175,"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/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.9390000104904175,"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":0.03909999877214432,"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/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.014399999752640724,"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/diels-alder-reaction","display_name":"Diels-Alder reaction","score":0.9919999837875366},{"id":"https://openalex.org/keywords/1-3-butadiene","display_name":"1,3-butadiene","score":0.9860000014305115},{"id":"https://openalex.org/keywords/ethylene","display_name":"ethylene","score":1.0},{"id":"https://openalex.org/keywords/concerted-mechanism","display_name":"concerted mechanism","score":0.8920000195503235},{"id":"https://openalex.org/keywords/stepwise-mechanism","display_name":"stepwise mechanism","score":0.9599999785423279},{"id":"https://openalex.org/keywords/spin-contamination","display_name":"spin contamination","score":0.7570000290870667},{"id":"https://openalex.org/keywords/spin-projection","display_name":"spin projection","score":0.6499999761581421},{"id":"https://openalex.org/keywords/kinetic-isotope-effects","display_name":"kinetic isotope effects","score":0.8560000061988831},{"id":"https://openalex.org/keywords/activation-free-energy","display_name":"activation free energy","score":0.7649999856948853},{"id":"https://openalex.org/keywords/reaction-energetics","display_name":"reaction energetics","score":0.6809999942779541}],"concepts":[{"id":"https://openalex.org/C117633835","wikidata":"https://www.wikidata.org/wiki/Q5280165","display_name":"Diradical","level":4,"score":0.9652925729751587},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8428936004638672},{"id":"https://openalex.org/C29135686","wikidata":"https://www.wikidata.org/wiki/Q2733609","display_name":"Concerted reaction","level":3,"score":0.8189929723739624},{"id":"https://openalex.org/C193609823","wikidata":"https://www.wikidata.org/wiki/Q3743359","display_name":"Stepwise reaction","level":5,"score":0.6549660563468933},{"id":"https://openalex.org/C152365726","wikidata":"https://www.wikidata.org/wiki/Q1048589","display_name":"Density functional theory","level":2,"score":0.6130770444869995},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.5970124006271362},{"id":"https://openalex.org/C69928629","wikidata":"https://www.wikidata.org/wiki/Q1386472","display_name":"Kinetic isotope effect","level":3,"score":0.5547223091125488},{"id":"https://openalex.org/C2778597550","wikidata":"https://www.wikidata.org/wiki/Q151313","display_name":"Ethylene","level":3,"score":0.5209947228431702},{"id":"https://openalex.org/C65024703","wikidata":"https://www.wikidata.org/wiki/Q373406","display_name":"Reaction mechanism","level":3,"score":0.5067020058631897},{"id":"https://openalex.org/C2779940776","wikidata":"https://www.wikidata.org/wiki/Q375669","display_name":"Diels\u2013Alder reaction","level":3,"score":0.5037803053855896},{"id":"https://openalex.org/C89031862","wikidata":"https://www.wikidata.org/wiki/Q906964","display_name":"Transition state","level":3,"score":0.4166385531425476},{"id":"https://openalex.org/C135889238","wikidata":"https://www.wikidata.org/wiki/Q46276","display_name":"Kinetic energy","level":2,"score":0.4105674922466278},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.3885428011417389},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.3281462490558624},{"id":"https://openalex.org/C93391505","wikidata":"https://www.wikidata.org/wiki/Q658700","display_name":"Reaction rate constant","level":3,"score":0.21688443422317505},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.18222972750663757},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.15822669863700867},{"id":"https://openalex.org/C135502975","wikidata":"https://www.wikidata.org/wiki/Q904041","display_name":"Order of reaction","level":4,"score":0.14210546016693115},{"id":"https://openalex.org/C184779094","wikidata":"https://www.wikidata.org/wiki/Q26383","display_name":"Atomic physics","level":1,"score":0.12683910131454468},{"id":"https://openalex.org/C148898269","wikidata":"https://www.wikidata.org/wiki/Q1108792","display_name":"Kinetics","level":2,"score":0.10114935040473938},{"id":"https://openalex.org/C181500209","wikidata":"https://www.wikidata.org/wiki/Q215328","display_name":"Excited state","level":2,"score":0.0686592161655426},{"id":"https://openalex.org/C33062035","wikidata":"https://www.wikidata.org/wiki/Q3296863","display_name":"Singlet state","level":3,"score":0.06260159611701965},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.06183558702468872},{"id":"https://openalex.org/C58364064","wikidata":"https://www.wikidata.org/wiki/Q102296","display_name":"Deuterium","level":2,"score":0.0},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/ja9601494","doi":"https://doi.org/10.1021/ja9601494","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja9601494","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":70,"referenced_works":["https://openalex.org/W285749399","https://openalex.org/W1965752906","https://openalex.org/W1969318209","https://openalex.org/W1978093738","https://openalex.org/W1979857834","https://openalex.org/W1981069414","https://openalex.org/W1985189982","https://openalex.org/W1985305274","https://openalex.org/W1989036084","https://openalex.org/W1989452109","https://openalex.org/W1990286684","https://openalex.org/W1997641598","https://openalex.org/W1998699452","https://openalex.org/W1999581086","https://openalex.org/W2000547662","https://openalex.org/W2001793909","https://openalex.org/W2006108048","https://openalex.org/W2006493612","https://openalex.org/W2006806329","https://openalex.org/W2007794165","https://openalex.org/W2008844584","https://openalex.org/W2012345116","https://openalex.org/W2012778107","https://openalex.org/W2013303436","https://openalex.org/W2017066406","https://openalex.org/W2020895640","https://openalex.org/W2022216240","https://openalex.org/W2023271753","https://openalex.org/W2023329300","https://openalex.org/W2024405014","https://openalex.org/W2024529715","https://openalex.org/W2027285150","https://openalex.org/W2027835645","https://openalex.org/W2029793661","https://openalex.org/W2031967166","https://openalex.org/W2034812398","https://openalex.org/W2035704128","https://openalex.org/W2038130165","https://openalex.org/W2043254020","https://openalex.org/W2043842244","https://openalex.org/W2044151658","https://openalex.org/W2045276120","https://openalex.org/W2045480642","https://openalex.org/W2045952721","https://openalex.org/W2049718200","https://openalex.org/W2051968588","https://openalex.org/W2055281064","https://openalex.org/W2058654558","https://openalex.org/W2060526159","https://openalex.org/W2061292441","https://openalex.org/W2066262976","https://openalex.org/W2071172619","https://openalex.org/W2072784880","https://openalex.org/W2073190710","https://openalex.org/W2078302795","https://openalex.org/W2079375920","https://openalex.org/W2087703290","https://openalex.org/W2088982706","https://openalex.org/W2114127602","https://openalex.org/W2114463368","https://openalex.org/W2115563016","https://openalex.org/W2143981217","https://openalex.org/W2155062117","https://openalex.org/W2159514058","https://openalex.org/W2161807477","https://openalex.org/W2230728100","https://openalex.org/W2331727781","https://openalex.org/W2949693121","https://openalex.org/W2951655311","https://openalex.org/W4250731460"],"related_works":["https://openalex.org/W2529308022","https://openalex.org/W2013303436","https://openalex.org/W1515744637","https://openalex.org/W2089316125","https://openalex.org/W2058320856","https://openalex.org/W7222952836","https://openalex.org/W2003022101","https://openalex.org/W2091360392","https://openalex.org/W2008680868","https://openalex.org/W1988907716"],"abstract_inverted_index":{"Density-functional":[0],"theory":[1],"has":[2,37],"been":[3],"applied":[4],"to":[5,64,110],"the":[6,9,12,29,48,54,70,78,82,87,93,99,105,129,161],"study":[7,68],"of":[8,11,15,41,47,53,69,84,102,124,128,173,178],"mechanism":[10,159],"Diels\u2212Alder":[13,106,165],"reaction":[14,107,125],"butadiene":[16,162],"and":[17,22,95,114,126,131,155,180],"ethylene.":[18],"Both":[19],"synchronous":[20],"concerted":[21,49,158,179],"two-step":[23],"diradical":[24,56,85,88],"mechanisms":[25],"were":[26],"studied":[27],"at":[28],"Becke3LYP/6-31G*":[30],"level.":[31],"The":[32,167],"lowest":[33],"energy":[34,40,59,62,74,101],"stepwise":[35,181],"pathway":[36],"a":[38,152,157],"free":[39,100],"activation":[42],"7.7":[43,115],"kcal/mol":[44],"above":[45],"that":[46,77],"path.":[50],"Spin":[51],"correction":[52],"spin-contaminated":[55],"transition":[57],"structure":[58],"reduces":[60],"this":[61],"difference":[63],"2.3":[65,113],"kcal/mol.":[66],"A":[67],"H":[71],"2":[72],"potential":[73],"surface":[75],"suggests":[76],"spin-projection":[79],"procedure":[80],"overcorrects":[81],"energies":[83,89],"species;":[86],"likely":[90],"fall":[91],"between":[92,112],"corrected":[94],"uncorrected":[96],"values.":[97],"Thus,":[98],"concert":[103],"for":[104,160],"is":[108,171],"predicted":[109],"be":[111],"kcal/mol,":[116],"in":[117,134],"excellent":[118],"agreement":[119,136],"with":[120,137,148],"thermochemical":[121],"estimates.":[122],"Energies":[123],"geometries":[127],"reactants":[130],"product":[132],"are":[133],"good":[135],"available":[138],"experimental":[139,149],"results.":[140],"Calculated":[141],"secondary":[142],"kinetic":[143],"isotope":[144],"effects":[145],"agree":[146],"well":[147],"data":[150],"on":[151],"related":[153],"reaction,":[154],"support":[156],"plus":[163],"ethylene":[164],"reaction.":[166],"Becke3LYP":[168],"DFT":[169],"method":[170],"capable":[172],"relatively":[174],"economical":[175],"direct":[176],"comparisons":[177],"mechanisms.":[182]},"counts_by_year":[{"year":2026,"cited_by_count":5},{"year":2025,"cited_by_count":6},{"year":2024,"cited_by_count":6},{"year":2023,"cited_by_count":7},{"year":2022,"cited_by_count":7},{"year":2021,"cited_by_count":7},{"year":2020,"cited_by_count":10},{"year":2019,"cited_by_count":11},{"year":2018,"cited_by_count":11},{"year":2017,"cited_by_count":15},{"year":2016,"cited_by_count":13},{"year":2015,"cited_by_count":18},{"year":2014,"cited_by_count":20},{"year":2013,"cited_by_count":11},{"year":2012,"cited_by_count":14}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}
