{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T07:34:28Z","timestamp":1776324868156,"version":"3.50.1"},"reference-count":104,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2025,1,27]],"date-time":"2025-01-27T00:00:00Z","timestamp":1737936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["313833\/2021\u20104"],"award-info":[{"award-number":["313833\/2021\u20104"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006162","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Ci\u00eancia e Tecnologia do Estado de Pernambuco","doi-asserted-by":"publisher","award":["APQ\u20100792\u20101.06\/14"],"award-info":[{"award-number":["APQ\u20100792\u20101.06\/14"]}],"id":[{"id":"10.13039\/501100006162","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","award":["88881.159185\/2017\u201001"],"award-info":[{"award-number":["88881.159185\/2017\u201001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Comput Chem"],"published-print":{"date-parts":[[2025,1,30]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>While established guidelines exist for chirality in tetrahedral molecules, there is a notable absence of clear rules for recognizing metal\u2010centered chirality in higher\u2010coordination complexes. We develop decision trees to assess the likelihood of chirality\u2010at\u2010metal in coordination complexes with coordination numbers 4\u20139 with mono and bidentate ligands. Using binary decision rules based on shape, ligand type, and quantity, the trees classify complexes as chiral or achiral. The theoretical formalism employs stereoisomer enumeration via P\u00f3lya's theorem, assuming ideal geometries and <jats:italic>cis<\/jats:italic> coordination of bidentate ligands. Additionally, analysis of over 2700 crystallographic structures reveals a high prevalence of metal\u2010centered chirality, especially in complexes with higher coordination numbers. These powerful yet easy\u2010to\u2010use decision trees provide chemists with deeper insights into the stereochemistry of metal coordination complexes and with effective tools to identify and understand this often\u2010overlooked stereochemical property and its impact on molecular interactions and crystal packing.<\/jats:p>","DOI":"10.1002\/jcc.70025","type":"journal-article","created":{"date-parts":[[2025,1,27]],"date-time":"2025-01-27T12:23:12Z","timestamp":1737980592000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Decision Trees for the Recognition of Metal\u2010Centered Chirality in Coordination Complexes"],"prefix":"10.1002","volume":"46","author":[{"given":"Gabriel H. L.","family":"Munguba","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Fundamental Universidade Federal de Pernambuco  Recife Pernambuco Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mateus F.","family":"da Silva","sequence":"additional","affiliation":[{"name":"Departamento de Matem\u00e1tica Universidade Federal de Pernambuco  Recife Pernambuco Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Frederico T.","family":"Silva","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Fundamental Universidade Federal de Pernambuco  Recife Pernambuco Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gabriel A.","family":"Urquiza\u2010Carvalho","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Fundamental Universidade Federal de Pernambuco  Recife Pernambuco Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3653-6328","authenticated-orcid":false,"given":"Alfredo M.","family":"Simas","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Fundamental Universidade Federal de Pernambuco  Recife Pernambuco Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,1,27]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35270B"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.2c00724"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201700739"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC03101F"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2QO01930B"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev\u2010physchem\u2010040214\u2010121554"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1063\/5.0118582"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0DT01711F"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aar4265"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1007\/4243_2020_20"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.08.006"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/b909430j"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.2c02202"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202208326"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1TC05023K"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201603719"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23538"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004\u2010020\u201000366\u20101"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570\u2010020\u201000235\u20104"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2020.00555"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405584"},{"key":"e_1_2_8_23_1","first-page":"347","article-title":"Match Communications in Mathematical and in Computer","volume":"73","author":"Dobrowolski J.","year":"2015","journal-title":"Chemistry"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273316010846"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0567739473000963"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.8b01133"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426\u2010009\u20100261\u20102"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598\u2010021\u201099525\u20100"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.0c00503"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.26700"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.3c01313"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201038169\u20102"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35242g"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00604"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/advs.202307448"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2052520616003954"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02546665"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00547a020"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr990346w"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201700815"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1DT01050F"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50181a068"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.optmat.2023.114359"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576719000463"},{"key":"e_1_2_8_45_1","unstructured":"F. T.Silva \u201cEstereoqu\u00edmica em complexos met\u00e1licos: generaliza\u00e7\u00e3o das regras de Cahn\u2010Ingold\u2010Prelog enumera\u00e7\u00e3o quiralidade identifica\u00e7\u00e3o raz\u00f5es de coordena\u00e7\u00e3o aleat\u00f3ria e algoritmos\u201d (doctoral thesis Universidade Federal de Pernambuco 2018)."},{"key":"e_1_2_8_46_1","unstructured":"G.Landrum P.Tosco B.Kelley et\u00a0al. \u201crdkit\/rdkit: 2021_09_5 (Q3 2021) Release (Release_2021_09_5). Zenodo.\u201d(2022) https:\/\/doi.org\/10.5281\/zenodo.6330241."},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/ci100219f"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576718012724"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2052520620003601"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576721009109"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200390109"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.3390\/chemistry2030049"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2009.06.025"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.3390\/magnetochemistry9050131"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.3390\/cryst13020337"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1DT00365H"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/0010\u20108545(95)01187\u20100"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50006a001"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50113a021"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00744495"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099\u20100682(200106)2001:6<1499::AID\u2010EJIC1499>3.0.CO;2\u2010W"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/0020\u20101693(95)04989\u20104"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.6b01072"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.7b00273"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805608"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.inoche.2011.07.016"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3tc30686k"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8DT03585G"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic4011218"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA01741J"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.8b00294"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.synthmet.2011.03.016"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jlumin.2013.07.065"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1039\/B812292J"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt51380g"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.4236\/csta.2021.101001"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt51784e"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2019.119294"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2021.115077"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.9b03492"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.9b01411"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1039\/b614681c"},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.0c02480"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521\u20103749(200208)628:8<1885::AID\u2010ZAAC1885>3.0.CO;2\u20104"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11172\u2010023\u20103906\u2010y"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108768109053610"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229615002636"},{"key":"e_1_2_8_88_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC08638A"},{"key":"e_1_2_8_89_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c13180"},{"key":"e_1_2_8_90_1","doi-asserted-by":"publisher","DOI":"10.3390\/magnetochemistry3010002"},{"key":"e_1_2_8_91_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.8b02830"},{"key":"e_1_2_8_92_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201190"},{"key":"e_1_2_8_93_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2017.12.035"},{"key":"e_1_2_8_94_1","doi-asserted-by":"publisher","DOI":"10.1039\/b924547b"},{"key":"e_1_2_8_95_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic0606633"},{"key":"e_1_2_8_96_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic201851r"},{"key":"e_1_2_8_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic901663w"},{"key":"e_1_2_8_98_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1nj20430k"},{"key":"e_1_2_8_99_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic202467f"},{"key":"e_1_2_8_100_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep02395"},{"key":"e_1_2_8_101_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.7b00647"},{"key":"e_1_2_8_102_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC01042G"},{"key":"e_1_2_8_103_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200401019"},{"key":"e_1_2_8_104_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02097"},{"key":"e_1_2_8_105_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic048199u"}],"container-title":["Journal of Computational Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jcc.70025","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,2]],"date-time":"2025-05-02T12:31:49Z","timestamp":1746189109000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jcc.70025"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,27]]},"references-count":104,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2025,1,30]]}},"alternative-id":["10.1002\/jcc.70025"],"URL":"https:\/\/doi.org\/10.1002\/jcc.70025","archive":["Portico"],"relation":{},"ISSN":["0192-8651","1096-987X"],"issn-type":[{"value":"0192-8651","type":"print"},{"value":"1096-987X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,1,27]]},"assertion":[{"value":"2024-09-23","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-12-16","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-01-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70025"}}