{"id":"https://openalex.org/W3148755803","doi":"https://doi.org/10.3390/sym13040627","title":"A Concise Synthesis of a Methyl Ester 2-Resorcinarene: A Chair-Conformation Macrocycle","display_name":"A Concise Synthesis of a Methyl Ester 2-Resorcinarene: A Chair-Conformation Macrocycle","publication_year":2021,"publication_date":"2021-04-09","ids":{"openalex":"https://openalex.org/W3148755803","doi":"https://doi.org/10.3390/sym13040627","mag":"3148755803"},"language":"en","primary_location":{"id":"doi:10.3390/sym13040627","is_oa":true,"landing_page_url":"https://doi.org/10.3390/sym13040627","pdf_url":"https://www.mdpi.com/2073-8994/13/4/627/pdf?version=1617949695","source":{"id":"https://openalex.org/S190787756","display_name":"Symmetry","issn_l":"2073-8994","issn":["2073-8994"],"is_oa":true,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Symmetry","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","doaj"],"open_access":{"is_oa":true,"oa_status":"gold","oa_url":"https://www.mdpi.com/2073-8994/13/4/627/pdf?version=1617949695","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5064232919","display_name":"Michael R. Reynolds","orcid":"https://orcid.org/0000-0002-8723-930X"},"institutions":[{"id":"https://openalex.org/I74413500","display_name":"University of Windsor","ror":"https://ror.org/01gw3d370","country_code":"CA","type":"education","lineage":["https://openalex.org/I74413500"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Michael R. Reynolds","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada"],"raw_orcid":"https://orcid.org/0000-0002-8723-930X","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada","institution_ids":["https://openalex.org/I74413500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5065513106","display_name":"Fraser S. Pick","orcid":"https://orcid.org/0000-0001-8629-6065"},"institutions":[{"id":"https://openalex.org/I74413500","display_name":"University of Windsor","ror":"https://ror.org/01gw3d370","country_code":"CA","type":"education","lineage":["https://openalex.org/I74413500"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Fraser S. Pick","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada"],"raw_orcid":"https://orcid.org/0000-0001-8629-6065","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada","institution_ids":["https://openalex.org/I74413500"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016479297","display_name":"John J. Hayward","orcid":"https://orcid.org/0000-0002-7502-7780"},"institutions":[{"id":"https://openalex.org/I74413500","display_name":"University of Windsor","ror":"https://ror.org/01gw3d370","country_code":"CA","type":"education","lineage":["https://openalex.org/I74413500"]}],"countries":["CA"],"is_corresponding":true,"raw_author_name":"John J. Hayward","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada","institution_ids":["https://openalex.org/I74413500"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074586905","display_name":"John F. Trant","orcid":"https://orcid.org/0000-0002-4780-4968"},"institutions":[{"id":"https://openalex.org/I74413500","display_name":"University of Windsor","ror":"https://ror.org/01gw3d370","country_code":"CA","type":"education","lineage":["https://openalex.org/I74413500"]}],"countries":["CA"],"is_corresponding":true,"raw_author_name":"John F. Trant","raw_affiliation_strings":["Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada"],"raw_orcid":"https://orcid.org/0000-0002-4780-4968","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Ave., Windsor, ON N9B 3P4, Canada","institution_ids":["https://openalex.org/I74413500"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5016479297","https://openalex.org/A5074586905"],"corresponding_institution_ids":["https://openalex.org/I74413500"],"apc_list":{"value":2000,"currency":"CHF","value_usd":2165},"apc_paid":{"value":2000,"currency":"CHF","value_usd":2165},"fwci":0.227,"has_fulltext":true,"cited_by_count":2,"citation_normalized_percentile":{"value":0.48479051,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":90,"max":94},"biblio":{"volume":"13","issue":"4","first_page":"627","last_page":"627"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10532","display_name":"Molecular Sensors and Ion Detection","score":1.0,"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/T10532","display_name":"Molecular Sensors and Ion Detection","score":1.0,"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/T10578","display_name":"Supramolecular Chemistry and Complexes","score":0.9998999834060669,"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/T11240","display_name":"Luminescence and Fluorescent Materials","score":0.9993000030517578,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/resorcinarene","display_name":"Resorcinarene","score":0.9922845363616943},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.8677464127540588},{"id":"https://openalex.org/keywords/substituent","display_name":"Substituent","score":0.7633994817733765},{"id":"https://openalex.org/keywords/hydrogen-bond","display_name":"Hydrogen bond","score":0.7006628513336182},{"id":"https://openalex.org/keywords/cavitand","display_name":"Cavitand","score":0.544620931148529},{"id":"https://openalex.org/keywords/combinatorial-chemistry","display_name":"Combinatorial chemistry","score":0.465539813041687},{"id":"https://openalex.org/keywords/electrophile","display_name":"Electrophile","score":0.4320048987865448},{"id":"https://openalex.org/keywords/density-functional-theory","display_name":"Density functional theory","score":0.41180557012557983},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"Computational chemistry","score":0.3966616690158844},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"Stereochemistry","score":0.3428076505661011},{"id":"https://openalex.org/keywords/molecule","display_name":"Molecule","score":0.33028721809387207},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.2743956446647644},{"id":"https://openalex.org/keywords/supramolecular-chemistry","display_name":"Supramolecular chemistry","score":0.20870652794837952},{"id":"https://openalex.org/keywords/catalysis","display_name":"Catalysis","score":0.17231976985931396}],"concepts":[{"id":"https://openalex.org/C163893822","wikidata":"https://www.wikidata.org/wiki/Q1402811","display_name":"Resorcinarene","level":3,"score":0.9922845363616943},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8677464127540588},{"id":"https://openalex.org/C2778689049","wikidata":"https://www.wikidata.org/wiki/Q898422","display_name":"Substituent","level":2,"score":0.7633994817733765},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.7006628513336182},{"id":"https://openalex.org/C69169829","wikidata":"https://www.wikidata.org/wiki/Q3663992","display_name":"Cavitand","level":4,"score":0.544620931148529},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.465539813041687},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.4320048987865448},{"id":"https://openalex.org/C152365726","wikidata":"https://www.wikidata.org/wiki/Q1048589","display_name":"Density functional theory","level":2,"score":0.41180557012557983},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3966616690158844},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3428076505661011},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.33028721809387207},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2743956446647644},{"id":"https://openalex.org/C93275456","wikidata":"https://www.wikidata.org/wiki/Q756449","display_name":"Supramolecular chemistry","level":3,"score":0.20870652794837952},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.17231976985931396}],"mesh":[],"locations_count":4,"locations":[{"id":"doi:10.3390/sym13040627","is_oa":true,"landing_page_url":"https://doi.org/10.3390/sym13040627","pdf_url":"https://www.mdpi.com/2073-8994/13/4/627/pdf?version=1617949695","source":{"id":"https://openalex.org/S190787756","display_name":"Symmetry","issn_l":"2073-8994","issn":["2073-8994"],"is_oa":true,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Symmetry","raw_type":"journal-article"},{"id":"pmh:oai:doaj.org/article:1f530bdd67f948a3849a96b701567bcb","is_oa":true,"landing_page_url":"https://doaj.org/article/1f530bdd67f948a3849a96b701567bcb","pdf_url":null,"source":{"id":"https://openalex.org/S4306401280","display_name":"DOAJ (DOAJ: Directory of Open Access Journals)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-sa","license_id":"https://openalex.org/licenses/cc-by-sa","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Symmetry, Vol 13, Iss 4, p 627 (2021)","raw_type":"article"},{"id":"pmh:oai:mdpi.com:/2073-8994/13/4/627/","is_oa":true,"landing_page_url":"https://dx.doi.org/10.3390/sym13040627","pdf_url":null,"source":{"id":"https://openalex.org/S4306400947","display_name":"MDPI (MDPI AG)","issn_l":null,"issn":null,"is_oa":true,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I4210097602","host_organization_name":"Multidisciplinary Digital Publishing Institute (Switzerland)","host_organization_lineage":["https://openalex.org/I4210097602"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Symmetry","raw_type":"Text"},{"id":"pmh:oai:scholar.uwindsor.ca:chemistrybiochemistrypub-1178","is_oa":false,"landing_page_url":"https://scholar.uwindsor.ca/chemistrybiochemistrypub/176","pdf_url":null,"source":{"id":"https://openalex.org/S4306400430","display_name":"Scholarship at UWindsor (University of Windsor)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I74413500","host_organization_name":"University of Windsor","host_organization_lineage":["https://openalex.org/I74413500"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Chemistry and Biochemistry Publications","raw_type":"text"}],"best_oa_location":{"id":"doi:10.3390/sym13040627","is_oa":true,"landing_page_url":"https://doi.org/10.3390/sym13040627","pdf_url":"https://www.mdpi.com/2073-8994/13/4/627/pdf?version=1617949695","source":{"id":"https://openalex.org/S190787756","display_name":"Symmetry","issn_l":"2073-8994","issn":["2073-8994"],"is_oa":true,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Symmetry","raw_type":"journal-article"},"sustainable_development_goals":[{"display_name":"Life in Land","score":0.4699999988079071,"id":"https://metadata.un.org/sdg/15"}],"awards":[{"id":"https://openalex.org/G7199297558","display_name":null,"funder_award_id":"2018-06338","funder_id":"https://openalex.org/F4320334593","funder_display_name":"Natural Sciences and Engineering Research Council of Canada"},{"id":"https://openalex.org/G8698879259","display_name":null,"funder_award_id":"IT13760","funder_id":"https://openalex.org/F4320322675","funder_display_name":"Mitacs"}],"funders":[{"id":"https://openalex.org/F4320311065","display_name":"University of Windsor","ror":"https://ror.org/01gw3d370"},{"id":"https://openalex.org/F4320322675","display_name":"Mitacs","ror":"https://ror.org/00cjrc276"},{"id":"https://openalex.org/F4320334593","display_name":"Natural Sciences and Engineering Research Council of Canada","ror":"https://ror.org/01h531d29"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W3148755803.pdf","grobid_xml":"https://content.openalex.org/works/W3148755803.grobid-xml"},"referenced_works_count":36,"referenced_works":["https://openalex.org/W1912487092","https://openalex.org/W1969790946","https://openalex.org/W1971275758","https://openalex.org/W1980631469","https://openalex.org/W1996313795","https://openalex.org/W2001264652","https://openalex.org/W2011033015","https://openalex.org/W2015074523","https://openalex.org/W2019116211","https://openalex.org/W2020598466","https://openalex.org/W2023041506","https://openalex.org/W2034793276","https://openalex.org/W2034953462","https://openalex.org/W2035216728","https://openalex.org/W2038938143","https://openalex.org/W2042229177","https://openalex.org/W2042269168","https://openalex.org/W2043723408","https://openalex.org/W2054812539","https://openalex.org/W2059205366","https://openalex.org/W2063334178","https://openalex.org/W2076307173","https://openalex.org/W2109834426","https://openalex.org/W2112850441","https://openalex.org/W2122339070","https://openalex.org/W2124860710","https://openalex.org/W2136918864","https://openalex.org/W2150275072","https://openalex.org/W2161285339","https://openalex.org/W2162544674","https://openalex.org/W2625094404","https://openalex.org/W2772725207","https://openalex.org/W2858058544","https://openalex.org/W2902288565","https://openalex.org/W3012338980","https://openalex.org/W4211173318"],"related_works":["https://openalex.org/W4310154372","https://openalex.org/W4285228126","https://openalex.org/W2124732865","https://openalex.org/W2051518275","https://openalex.org/W2073487402","https://openalex.org/W2071081340","https://openalex.org/W2614515353","https://openalex.org/W2094632951","https://openalex.org/W2002810878","https://openalex.org/W2334222235"],"abstract_inverted_index":{"Anions":[0],"are":[1],"important":[2],"hydrogen":[3,33,143,185],"bond":[4,34,144],"acceptors":[5,145],"in":[6,117],"a":[7,106,112,156,170],"range":[8],"of":[9,28,42,66,83,135,152,172,177,182],"biological,":[10],"chemical,":[11],"environmental":[12],"and":[13,26,114,126,180],"medical":[14],"molecular":[15],"recognition":[16,92],"processes.":[17],"These":[18],"interactions":[19],"have":[20,58],"been":[21,60],"exploited":[22],"for":[23,110],"the":[24,32,40,43,46,64,121,132,136,147,173,183,188],"design":[25],"synthesis":[27],"ditopic":[29],"resorcinarenes":[30,89],"as":[31,90,155,169],"strength":[35],"can":[36],"be":[37],"tuned":[38],"through":[39],"modification":[41],"substituent":[44],"at":[45],"2-position.":[47],"However,":[48],"many":[49],"potentially":[50],"useful":[51],"compounds,":[52],"especially":[53],"those":[54],"incorporating":[55],"electron-withdrawing":[56,133],"functionalities,":[57],"not":[59],"prepared":[61],"due":[62],"to":[63,87,97],"challenge":[65],"their":[67,69],"synthesis:":[68],"incorporation":[70],"slows":[71],"resorcinarene":[72,115],"formation":[73],"that":[74,128,139,150,165],"is":[75],"accessed":[76],"by":[77,187],"electrophilic":[78],"aromatic":[79],"substitution.":[80],"As":[81],"part":[82],"our":[84],"broader":[85],"campaign":[86],"employ":[88],"selective":[91],"elements,":[93],"we":[94,104],"need":[95],"access":[96],"these":[98],"specialized":[99],"materials.":[100],"In":[101],"this":[102,129,166,178],"article,":[103],"report":[105],"straightforward":[107],"synthetic":[108],"pathway":[109],"obtaining":[111],"2-(carboxymethyl)-resorcinarene,":[113],"esters":[116],"general.":[118],"We":[119],"discuss":[120],"unusual":[122,174],"conformation":[123,167],"it":[124],"adopts":[125],"propose":[127],"arises":[130,168],"from":[131],"nature":[134],"ester":[137,189],"substituents":[138],"renders":[140],"them":[141,153],"better":[142],"than":[146],"phenols,":[148],"ensuring":[149],"each":[151],"acts":[154],"donor":[157],"only.":[158],"Density":[159],"Functional":[160],"Theory":[161],"(DFT)":[162],"calculations":[163],"show":[164],"consequence":[171],"configurational":[175],"isomerism":[176],"compound":[179],"interruption":[181],"archetypal":[184],"bonding":[186],"functionality.":[190]},"counts_by_year":[{"year":2024,"cited_by_count":1},{"year":2022,"cited_by_count":1}],"updated_date":"2026-05-21T06:26:12.895304","created_date":"2025-10-10T00:00:00"}