{"id":"https://openalex.org/W2965447776","doi":"https://doi.org/10.1021/acs.jcim.9b00313","title":"Learning To Predict Reaction Conditions: Relationships between Solvent, Molecular Structure, and Catalyst","display_name":"Learning To Predict Reaction Conditions: Relationships between Solvent, Molecular Structure, and Catalyst","publication_year":2019,"publication_date":"2019-08-05","ids":{"openalex":"https://openalex.org/W2965447776","doi":"https://doi.org/10.1021/acs.jcim.9b00313","mag":"2965447776","pmid":"https://pubmed.ncbi.nlm.nih.gov/31381340"},"language":"en","primary_location":{"id":"doi:10.1021/acs.jcim.9b00313","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.9b00313","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"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 Information and Modeling","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7167595","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5060805106","display_name":"Eric A. Walker","orcid":"https://orcid.org/0000-0002-8125-7160"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Eric Walker","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5009402523","display_name":"Joshua Kammeraad","orcid":"https://orcid.org/0000-0003-0386-7198"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Joshua Kammeraad","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":"https://orcid.org/0000-0003-0386-7198","affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5077364135","display_name":"Jonathan Goetz","orcid":null},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jonathan Goetz","raw_affiliation_strings":["Department of Statistics, University of Michigan, 1085 South University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Statistics, University of Michigan, 1085 South University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5084845045","display_name":"Michael T. Robo","orcid":"https://orcid.org/0000-0003-1356-246X"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michael T. Robo","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5051918150","display_name":"Ambuj Tewari","orcid":"https://orcid.org/0000-0001-6969-7844"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ambuj Tewari","raw_affiliation_strings":["Department of Statistics, University of Michigan, 1085 South University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Statistics, University of Michigan, 1085 South University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5042777510","display_name":"Paul M. Zimmerman","orcid":"https://orcid.org/0000-0002-7444-1314"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Paul M. Zimmerman","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States"],"raw_orcid":"https://orcid.org/0000-0002-7444-1314","affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":6,"corresponding_author_ids":["https://openalex.org/A5042777510"],"corresponding_institution_ids":["https://openalex.org/I27837315"],"apc_list":null,"apc_paid":null,"fwci":3.3043,"has_fulltext":false,"cited_by_count":64,"citation_normalized_percentile":{"value":0.93198069,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":95,"max":100},"biblio":{"volume":"59","issue":"9","first_page":"3645","last_page":"3654"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11948","display_name":"Machine Learning in Materials Science","score":0.9995999932289124,"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"}},"topics":[{"id":"https://openalex.org/T11948","display_name":"Machine Learning in Materials Science","score":0.9995999932289124,"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"}},{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":0.9994999766349792,"subfield":{"id":"https://openalex.org/subfields/1703","display_name":"Computational Theory and Mathematics"},"field":{"id":"https://openalex.org/fields/17","display_name":"Computer Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12327","display_name":"Various Chemistry Research Topics","score":0.9800000190734863,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical 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/computer-science","display_name":"Computer science","score":0.6026982069015503},{"id":"https://openalex.org/keywords/speciality-chemicals","display_name":"Speciality chemicals","score":0.5172168016433716},{"id":"https://openalex.org/keywords/artificial-neural-network","display_name":"Artificial neural network","score":0.48942676186561584},{"id":"https://openalex.org/keywords/artificial-intelligence","display_name":"Artificial intelligence","score":0.47771549224853516},{"id":"https://openalex.org/keywords/cluster-analysis","display_name":"Cluster analysis","score":0.4332507252693176},{"id":"https://openalex.org/keywords/machine-learning","display_name":"Machine learning","score":0.40606868267059326},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.35602542757987976},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.18963885307312012}],"concepts":[{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.6026982069015503},{"id":"https://openalex.org/C142692745","wikidata":"https://www.wikidata.org/wiki/Q2309453","display_name":"Speciality chemicals","level":2,"score":0.5172168016433716},{"id":"https://openalex.org/C50644808","wikidata":"https://www.wikidata.org/wiki/Q192776","display_name":"Artificial neural network","level":2,"score":0.48942676186561584},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.47771549224853516},{"id":"https://openalex.org/C73555534","wikidata":"https://www.wikidata.org/wiki/Q622825","display_name":"Cluster analysis","level":2,"score":0.4332507252693176},{"id":"https://openalex.org/C119857082","wikidata":"https://www.wikidata.org/wiki/Q2539","display_name":"Machine learning","level":1,"score":0.40606868267059326},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.35602542757987976},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.18963885307312012}],"mesh":[{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"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":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006801","descriptor_name":"Humans","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008956","descriptor_name":"Models, Chemical","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D008956","descriptor_name":"Models, Chemical","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D008956","descriptor_name":"Models, Chemical","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D012997","descriptor_name":"Solvents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D012997","descriptor_name":"Solvents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D012997","descriptor_name":"Solvents","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D061565","descriptor_name":"Cycloaddition Reaction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D061565","descriptor_name":"Cycloaddition Reaction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D061565","descriptor_name":"Cycloaddition Reaction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.jcim.9b00313","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.9b00313","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"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 Information and Modeling","raw_type":"journal-article"},{"id":"pmid:31381340","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/31381340","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 chemical information and modeling","raw_type":null},{"id":"pmh:oai:pubmedcentral.nih.gov:7167595","is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7167595","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Chem Inf Model","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:7167595","is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/7167595","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Chem Inf Model","raw_type":"Text"},"sustainable_development_goals":[],"awards":[{"id":"https://openalex.org/G206600186","display_name":null,"funder_award_id":"R35GM128830","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G2068517436","display_name":null,"funder_award_id":"CHE1551994","funder_id":"https://openalex.org/F4320306076","funder_display_name":"National Science Foundation"},{"id":"https://openalex.org/G7284099862","display_name":null,"funder_award_id":"R35 GM128830","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":56,"referenced_works":["https://openalex.org/W1531524766","https://openalex.org/W1596717185","https://openalex.org/W1645857052","https://openalex.org/W1965269139","https://openalex.org/W1973166400","https://openalex.org/W1975147762","https://openalex.org/W1981233308","https://openalex.org/W1987470703","https://openalex.org/W1997974358","https://openalex.org/W1999798000","https://openalex.org/W2000614400","https://openalex.org/W2013394318","https://openalex.org/W2015255122","https://openalex.org/W2026265322","https://openalex.org/W2028695285","https://openalex.org/W2038702914","https://openalex.org/W2040010296","https://openalex.org/W2041258965","https://openalex.org/W2081301924","https://openalex.org/W2093566593","https://openalex.org/W2101234009","https://openalex.org/W2105966118","https://openalex.org/W2122111042","https://openalex.org/W2125910575","https://openalex.org/W2149423510","https://openalex.org/W2151697120","https://openalex.org/W2154190962","https://openalex.org/W2169678694","https://openalex.org/W2176574962","https://openalex.org/W2200017991","https://openalex.org/W2278722429","https://openalex.org/W2284262441","https://openalex.org/W2324964582","https://openalex.org/W2326357031","https://openalex.org/W2347129741","https://openalex.org/W2477622860","https://openalex.org/W2512660405","https://openalex.org/W2529099292","https://openalex.org/W2529996553","https://openalex.org/W2540880742","https://openalex.org/W2555690472","https://openalex.org/W2578240541","https://openalex.org/W2580919858","https://openalex.org/W2586210924","https://openalex.org/W2606363443","https://openalex.org/W2619496425","https://openalex.org/W2747592475","https://openalex.org/W2752506093","https://openalex.org/W2775684663","https://openalex.org/W2789913372","https://openalex.org/W2794704841","https://openalex.org/W2901942917","https://openalex.org/W2976658410","https://openalex.org/W3022436500","https://openalex.org/W3098269892","https://openalex.org/W3100545487"],"related_works":["https://openalex.org/W2961085424","https://openalex.org/W4306674287","https://openalex.org/W3046775127","https://openalex.org/W3107602296","https://openalex.org/W4394896187","https://openalex.org/W3170094116","https://openalex.org/W4386462264","https://openalex.org/W4364306694","https://openalex.org/W4312192474","https://openalex.org/W4283697347"],"abstract_inverted_index":{"Reaction":[0],"databases":[1],"provide":[2,17],"a":[3,113,136,159,164],"great":[4],"deal":[5],"of":[6,12,44,108,125,174,202],"useful":[7],"information":[8],"to":[9,23,50,94],"assist":[10],"planning":[11,131],"experiments":[13],"but":[14],"do":[15],"not":[16],"any":[18],"interpretation":[19],"or":[20],"chemical":[21,104],"concepts":[22],"accompany":[24],"this":[25,28,52,56,126],"information.":[26,53],"In":[27,54],"work,":[29],"reactions":[30,71,92],"are":[31,65,150],"labeled":[32],"with":[33,183],"experimental":[34,61],"conditions,":[35],"and":[36,78,103,163],"network":[37,152,181,193],"analysis":[38,57,87,153,194],"shows":[39,58,88],"that":[40,98,138,207],"consistencies":[41],"within":[42,82],"clusters":[43,97],"data":[45,89],"points":[46,90],"can":[47],"be":[48],"leveraged":[49],"organize":[51],"particular,":[55],"how":[59,112],"particular":[60],"conditions":[62],"(specifically":[63],"solvent)":[64],"effective":[66],"in":[67,135,172,218],"enabling":[68],"specific":[69],"organic":[70],"(Friedel\u2013Crafts,":[72],"Aldol":[73],"addition,":[74],"Claisen":[75],"condensation,":[76],"Diels\u2013Alder,":[77],"Wittig),":[79],"including":[80],"variations":[81],"each":[83],"reaction":[84],"class.":[85],"Network":[86],"for":[91,222],"tend":[93],"break":[95],"into":[96],"depend":[99],"on":[100],"the":[101,120,123,155,175,180,208,219],"catalyst":[102],"structure.":[105],"This":[106],"type":[107],"clustering,":[109],"which":[110],"mimics":[111,139],"chemist":[114],"reasons,":[115],"is":[116,179],"derived":[117],"directly":[118],"from":[119],"network.":[121,167],"Therefore,":[122],"findings":[124],"work":[127],"could":[128],"augment":[129],"synthesis":[130],"by":[132,198],"providing":[133],"predictions":[134],"fashion":[137],"human":[140],"chemists.":[141],"To":[142],"numerically":[143],"evaluate":[144],"solvent":[145,212],"prediction":[146,190],"ability,":[147],"three":[148],"methods":[149],"compared:":[151],"(through":[154],"k-nearest":[156],"neighbor":[157],"algorithm),":[158],"support":[160],"vector":[161],"machine,":[162],"deep":[165,184],"neural":[166,185],"The":[168,192],"most":[169],"accurate":[170,211],"method":[171],"4":[173],"5":[176],"test":[177],"cases":[178],"analysis,":[182],"networks":[186],"also":[187],"showing":[188],"good":[189],"scores.":[191],"tool":[195],"was":[196],"evaluated":[197],"an":[199],"expert":[200],"panel":[201],"chemists,":[203],"who":[204],"generally":[205],"agreed":[206],"algorithm":[209],"produced":[210],"choices":[213],"while":[214],"simultaneously":[215],"being":[216],"transparent":[217],"underlying":[220],"reasons":[221],"its":[223],"predictions.":[224]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":11},{"year":2024,"cited_by_count":6},{"year":2023,"cited_by_count":10},{"year":2022,"cited_by_count":10},{"year":2021,"cited_by_count":16},{"year":2020,"cited_by_count":10}],"updated_date":"2026-06-24T13:16:06.693445","created_date":"2025-10-10T00:00:00"}
