{"id":"https://openalex.org/W2010549674","doi":"https://doi.org/10.1021/ja011685l","title":"NMR Experimental Evidence of the Differentiation of Enantiotopic Directions inCsandC2vMolecules Using Partially Oriented, Chiral Media","display_name":"NMR Experimental Evidence of the Differentiation of Enantiotopic Directions inCsandC2vMolecules Using Partially Oriented, Chiral Media","publication_year":2001,"publication_date":"2001-11-07","ids":{"openalex":"https://openalex.org/W2010549674","doi":"https://doi.org/10.1021/ja011685l","mag":"2010549674","pmid":"https://pubmed.ncbi.nlm.nih.gov/11724614"},"language":"en","primary_location":{"id":"doi:10.1021/ja011685l","doi":"https://doi.org/10.1021/ja011685l","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja011685l","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/A5056663279","display_name":"Christie Aroulanda","orcid":"https://orcid.org/0000-0001-8019-2097","observed_orcids":["https://orcid.org/0000-0001-8019-2097"]},"institutions":[{"id":"https://openalex.org/I102197404","display_name":"Universit\u00e9 Paris-Sud","ror":"https://ror.org/028rypz17","country_code":"FR","type":"education","lineage":["https://openalex.org/I102197404","https://openalex.org/I277688954"]},{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Christie Aroulanda","raw_affiliation_strings":["Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France","institution_ids":["https://openalex.org/I102197404","https://openalex.org/I1294671590"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5105889515","display_name":"Denis Merlet","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I102197404","display_name":"Universit\u00e9 Paris-Sud","ror":"https://ror.org/028rypz17","country_code":"FR","type":"education","lineage":["https://openalex.org/I102197404","https://openalex.org/I277688954"]},{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Denis Merlet","raw_affiliation_strings":["Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France","institution_ids":["https://openalex.org/I102197404","https://openalex.org/I1294671590"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5111750385","display_name":"Jacques M. Courtieu","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I102197404","display_name":"Universit\u00e9 Paris-Sud","ror":"https://ror.org/028rypz17","country_code":"FR","type":"education","lineage":["https://openalex.org/I102197404","https://openalex.org/I277688954"]},{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Jacques Courtieu","raw_affiliation_strings":["Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France","institution_ids":["https://openalex.org/I102197404","https://openalex.org/I1294671590"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5082043570","display_name":"Philippe Lesot","orcid":"https://orcid.org/0000-0002-5811-7530","observed_orcids":["https://orcid.org/0000-0002-5811-7530"]},"institutions":[{"id":"https://openalex.org/I102197404","display_name":"Universit\u00e9 Paris-Sud","ror":"https://ror.org/028rypz17","country_code":"FR","type":"education","lineage":["https://openalex.org/I102197404","https://openalex.org/I277688954"]},{"id":"https://openalex.org/I1294671590","display_name":"Centre National de la Recherche Scientifique","ror":"https://ror.org/02feahw73","country_code":"FR","type":"government","lineage":["https://openalex.org/I1294671590"]}],"countries":["FR"],"is_corresponding":true,"raw_author_name":"Philippe Lesot","raw_affiliation_strings":["Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France","Centre National de la Recherche Scientifique"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Laboratoire de Chimie Structurale Organique, CNRS ESA 8074, ICMO, Bat. 410, Universit\u00e9 de Paris-Sud, 91405 Orsay, France","institution_ids":["https://openalex.org/I102197404","https://openalex.org/I1294671590"]},{"raw_affiliation_string":"Centre National de la Recherche Scientifique","institution_ids":["https://openalex.org/I1294671590"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5082043570"],"corresponding_institution_ids":["https://openalex.org/I102197404","https://openalex.org/I1294671590"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.8316,"has_fulltext":false,"cited_by_count":76,"citation_normalized_percentile":{"value":0.91503441,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":87,"max":97},"biblio":{"volume":"123","issue":"48","first_page":"12059","last_page":"12066"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12748","display_name":"Molecular spectroscopy and chirality","score":0.9409000277519226,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"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/T12748","display_name":"Molecular spectroscopy and chirality","score":0.9409000277519226,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"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/T11809","display_name":"Advanced NMR Techniques and Applications","score":0.05130000039935112,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"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/T12527","display_name":"Chemistry and Stereochemistry Studies","score":0.0017999999690800905,"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/chiral-nmr","display_name":"chiral NMR","score":0.6489999890327454},{"id":"https://openalex.org/keywords/chiral-liquid-crystals","display_name":"chiral liquid crystals","score":0.5870000123977661},{"id":"https://openalex.org/keywords/cs-symmetry","display_name":"Cs symmetry","score":0.5720000267028809},{"id":"https://openalex.org/keywords/prochiral-molecules","display_name":"prochiral molecules","score":0.9070000052452087},{"id":"https://openalex.org/keywords/norbornadiene","display_name":"norbornadiene","score":0.9929999709129333},{"id":"https://openalex.org/keywords/poly-gamma-benzyl-l-glutamate","display_name":"poly(\u03b3-benzyl-L-glutamate)","score":0.9139999747276306},{"id":"https://openalex.org/keywords/malononitrile","display_name":"malononitrile","score":0.9789999723434448},{"id":"https://openalex.org/keywords/natural-abundance-13c-nmr","display_name":"natural abundance 13C NMR","score":0.6959999799728394}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8749109506607056},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.6969808340072632},{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.5918105244636536},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.5603795051574707},{"id":"https://openalex.org/C134195300","wikidata":"https://www.wikidata.org/wiki/Q902071","display_name":"Stereocenter","level":4,"score":0.4615929126739502},{"id":"https://openalex.org/C66974803","wikidata":"https://www.wikidata.org/wiki/Q10359898","display_name":"Nuclear magnetic resonance spectroscopy","level":2,"score":0.4512266218662262},{"id":"https://openalex.org/C2781311116","wikidata":"https://www.wikidata.org/wiki/Q83306","display_name":"Group (periodic table)","level":2,"score":0.4219432473182678},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.3710976839065552},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.2961910367012024},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.1576637625694275},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0935511589050293}],"mesh":[],"locations_count":3,"locations":[{"id":"doi:10.1021/ja011685l","doi":"https://doi.org/10.1021/ja011685l","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja011685l","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:11724614","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11724614","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:HAL:hal-02309135v1","doi":null,"is_oa":false,"landing_page_url":"https://hal.science/hal-02309135","pdf_url":null,"source":{"id":"https://openalex.org/S4306402512","display_name":"HAL","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4405252976","host_organization_name":"Centre pour la Communication Scientifique Directe","host_organization_lineage":["https://openalex.org/I4405252976"],"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, 2001, 123 (48), pp.12059-12066. &#x27E8;10.1021/ja011685l&#x27E9;","raw_type":"info:eu-repo/semantics/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":29,"referenced_works":["https://openalex.org/W373661721","https://openalex.org/W1530963981","https://openalex.org/W1970690459","https://openalex.org/W1972541734","https://openalex.org/W1973194665","https://openalex.org/W1977503203","https://openalex.org/W1987183960","https://openalex.org/W1994477510","https://openalex.org/W2005979467","https://openalex.org/W2022662530","https://openalex.org/W2029602679","https://openalex.org/W2039817232","https://openalex.org/W2040364770","https://openalex.org/W2047358358","https://openalex.org/W2047384699","https://openalex.org/W2053977942","https://openalex.org/W2057855936","https://openalex.org/W2065717284","https://openalex.org/W2067421301","https://openalex.org/W2068227670","https://openalex.org/W2069734146","https://openalex.org/W2070153427","https://openalex.org/W2077188417","https://openalex.org/W2077805880","https://openalex.org/W2080084835","https://openalex.org/W2092182103","https://openalex.org/W2097255973","https://openalex.org/W2326919266","https://openalex.org/W2334446442"],"related_works":["https://openalex.org/W1981173770","https://openalex.org/W596233521","https://openalex.org/W2074937826","https://openalex.org/W2481908839","https://openalex.org/W2950856251","https://openalex.org/W2085976450","https://openalex.org/W4247264230","https://openalex.org/W1972195646","https://openalex.org/W2047358358","https://openalex.org/W2087398774"],"abstract_inverted_index":{"We":[0],"report":[1],"new":[2],"and":[3,13,22,32,47,62,108,189,203,234],"explicit":[4],"experimental":[5],"evidence":[6],"of":[7,10,43,54,71,105,148,173,221],"the":[8,37,67,146,161,174,177,184,199,236],"differentiation":[9,70,147],"(1)H-(1)H,":[11],"(13)C-(1)H,":[12],"(13)C-(2)H":[14],"enantiotopic":[15,72,149,219],"directions":[16,73,150],"in":[17,25,51,74,91,112,122,151,193],"prochiral":[18],"molecules":[19,153,172],"with":[20,78],"C(s)":[21,107],"C(2v)symmetry":[23],"dissolved":[24],"a":[26,75,85,113],"chiral":[27,114,194],"liquid-crystalline":[28],"phase":[29],"using":[30,82],"(13)C":[31],"(2)H-[(1)H]":[33],"NMR":[34,69,103],"spectroscopy":[35],"at":[36],"natural":[38],"abundance":[39],"level.":[40],"The":[41,87,210],"case":[42],"endo-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic":[44],"anhydride,":[45],"bicyclo[2.2.1]hepta-2,5-diene,":[46],"ethyl":[48],"alcohol":[49],"oriented":[50,115,124],"organic":[52],"solutions":[53],"poly-gamma-benzyl-L-glutamate":[55],"(PBLG)":[56],"or":[57,195],"poly-epsilon-carbobenzyloxy-L-lysine":[58],"(PCBLL)":[59],"is":[60,135],"investigated":[61],"discussed.":[63],"Next,":[64],"we":[65],"describe":[66],"first":[68,162],"C(2v)":[76,109,152],"molecule":[77],"no":[79,155],"prostereogenic":[80,156],"carbon":[81],"malononitrile":[83],"as":[84,181,183],"model.":[86],"various":[88],"results":[89],"presented":[90],"this":[92],"work":[93],"experimentally":[94],"validate":[95,235],"our":[96],"recent":[97],"theoretical":[98],"arguments":[99],"which":[100,168],"predict":[101],"that":[102,170],"spectra":[104],"nonplanar":[106],"compounds":[110],"embedded":[111],"solvent":[116],"should":[117],"differ":[118],"from":[119,137],"those":[120],"recorded":[121],"nonchiral":[123],"media,":[125],"because":[126],"their":[127,138],"effective":[128],"molecular":[129,139],"symmetry":[130],"point":[131,140],"group":[132,141],"(interacting":[133],"molecule)":[134],"different":[136],"(isolated":[142],"molecule).":[143],"In":[144],"addition,":[145],"exhibiting":[154],"tetrahedral":[157],"center":[158],"illustrates":[159],"for":[160],"time":[163],"an":[164],"old":[165],"stereochemical":[166],"hypothesis":[167],"speculates":[169],"\"for":[171],"type":[175],"CXXYY.":[176],"two":[178,218,222],"X":[179,202],"groups":[180,186,205],"well":[182],"Y":[185,204],"are":[187,206],"equivalent":[188,223],"cannot":[190],"be":[191,215],"distinguished":[192],"achiral":[196],"circumstances.":[197],"However,":[198],"relationships":[200,213],"between":[201],"not":[207],"all":[208],"equivalent.":[209],"four":[211],"X-Y":[212],"may":[214],"ordered":[216],"into":[217],"sets":[220],"relationships\"":[224],"(Mislow,":[225],"K.;":[226],"Raban,":[227],"M.":[228],"Top.":[229],"Stereochem.":[230],"1967,":[231],"1,":[232],"1)":[233],"stereogenicity":[237],"concepts":[238],"proposed":[239],"more":[240],"recently":[241],"by":[242],"Fujita":[243],"(Fujita,":[244],"S.":[245],"J.":[246],"Am.":[247],"Chem.":[248],"Soc.":[249],"1990,":[250],"112,":[251],"3390).":[252]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2019,"cited_by_count":4},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":2},{"year":2016,"cited_by_count":3},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":3},{"year":2012,"cited_by_count":1}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}
