{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T21:09:03Z","timestamp":1790802543878,"version":"4.1.0"},"reference-count":81,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2024,11,3]],"date-time":"2024-11-03T00:00:00Z","timestamp":1730592000000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"},{"start":{"date-parts":[[2024,11,3]],"date-time":"2024-11-03T00:00:00Z","timestamp":1730592000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["2147956"],"award-info":[{"award-number":["2147956"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPhysChem"],"published-print":{"date-parts":[[2024,12,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Throughout the halogen bonding literature, electron withdrawing groups are relied upon heavily for tuning the interaction strength between the halogen bond donor and acceptor; however, the interplay of electronic effects associated with various substituents is less of a focus. This work utilizes computational techniques to study the degree of <jats:italic>\u03c3<\/jats:italic>\u2010 and <jats:italic>\u03c0<\/jats:italic>\u2010electron donating\/accepting character of electron withdrawing groups in a prescribed set of halo\u2010alkyne, halo\u2010benzene, and halo\u2010ethynyl benzene halogen bond donors. We examine how these factors affect the <jats:italic>\u03c3<\/jats:italic>\u2010hole magnitude of the donors as well as the binding strength of the corresponding complexes with an ammonia acceptor. Statistical analyses aid the interpretation of how these substituents influence the properties of the halogen bond donors and complexes, and show that the electron withdrawing groups that are both <jats:italic>\u03c3<\/jats:italic>\u2010 and <jats:italic>\u03c0<\/jats:italic>\u2010electron accepting form the strongest halogen bond complexes.<\/jats:p>","DOI":"10.1002\/cphc.202400607","type":"journal-article","created":{"date-parts":[[2024,9,2]],"date-time":"2024-09-02T13:20:55Z","timestamp":1725283255000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Illuminating the Performance of Electron Withdrawing Groups in Halogen Bonding"],"prefix":"10.1002","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5753-4260","authenticated-orcid":false,"given":"Daniel P.","family":"Devore","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Baylor University, One Bear Place 97348  Waco TX, 76798\u20137348 USA"},{"name":"Present address: Department of Chemistry Southern Methodist University  P.O. Box 750314 Dallas TX 75205 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas L.","family":"Ellington","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Baylor University, One Bear Place 97348  Waco TX, 76798\u20137348 USA"},{"name":"Present address: Department of Chemistry and Physics University of Tennessee Martin  554 University Street Martin TN 38238 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8452-2302","authenticated-orcid":false,"given":"Kevin L.","family":"Shuford","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Baylor University, One Bear Place 97348  Waco TX, 76798\u20137348 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,3]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2020.599064"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801452"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c01864"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC05475A"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201701676"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402128"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms24065530"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.5b00478"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229622011822"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2052520618017778"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/nsr\/nwaa170"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202113786"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1351\/PAC-REC-12-05-10"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-006-0130-2"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CP06793C"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1113"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp408151t"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg200888n"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24193610"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800128"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/c004189k"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00177e"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00484"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.1c03817"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.4213"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.comptc.2015.07.024"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.202200011"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01280a022"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00002a004"},{"key":"e_1_2_8_30_1","unstructured":"J.\u2005E. Leffler E. Grunwald Rates and Equilibria of Organic Reactions - As Treated by Statistical Thermodynamic and Extrathermodynamic Methods Dover Publications1963."},{"key":"e_1_2_8_31_1","unstructured":"N.\u2005B.\u2005N.\u2005B. Chapman J. Shorter Correlation analysis in chemistry : recent advances Plenum Press New York1978."},{"key":"e_1_2_8_32_1","doi-asserted-by":"crossref","unstructured":"S.\u2005H. Unger C. Hansch Quantitative Models of Steric Effects pages\u200591\u2013118 John Wiley & Sons Ltd1976.","DOI":"10.1002\/9780470171912.ch4"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.1530"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja970335p"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.3c02049"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00189"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8NJ00558C"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC01973H"},{"key":"e_1_2_8_39_1","author":"Devore D. P.","year":"2024","journal-title":"J. Phys. Chem. A"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00544a007"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.445134"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.449360"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.449486"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/0166-1280(88)80248-3"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00088a005"},{"key":"e_1_2_8_46_1","doi-asserted-by":"crossref","unstructured":"F. Weinhold J.\u2005E. Carpenter The Natural Bond Orbital Lewis Structure Concept for Molecules Radicals and Radical Ions in R. Naaman Z. Vager (Editors) The Structure of Small Molecules and Ions pages\u2005227\u2013236 Springer US Boston MA1988.","DOI":"10.1007\/978-1-4684-7424-4_24"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.456153"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.462569"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464303"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1622924"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp065887l"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP00242B"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct301064t"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP05628J"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct400185f"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1080\/00268977000101561"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1749433"},{"key":"e_1_2_8_59_1","doi-asserted-by":"crossref","unstructured":"D. Cremer E. Kraka Current Organic Chemistry 14 1524.","DOI":"10.2174\/138527210793563233"},{"key":"e_1_2_8_60_1","doi-asserted-by":"crossref","unstructured":"E. Kraka J.\u2005A. Larsson D. Cremer Generalization of the Badger Rule Based on the Use of Adiabatic Vibrational Modes chapter\u20054 pages\u2005105\u2013149 John Wiley & Sons Ltd2010.","DOI":"10.1002\/9783527633272.ch4"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.202200812"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1480"},{"key":"e_1_2_8_63_1","unstructured":"M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Gaussia\u00f116 Revision C.012016."},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp906341r"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00260a006"},{"key":"e_1_2_8_67_1","doi-asserted-by":"crossref","unstructured":"R.\u2005F.\u2005W. Bader T.\u2005T. Nguyen-Dang Quantum Theory of Atoms in Molecules\u2013Dalton Revisited in P.-O. L\u00f6wdin (Editor) Advances in Quantum Chemistry vol.\u200514 pages\u200563\u2013124 Academic Press1981.","DOI":"10.1016\/S0065-3276(08)60326-3"},{"key":"e_1_2_8_68_1","doi-asserted-by":"crossref","unstructured":"P. Politzer J.\u2005S. Murray Molecular Electrostatic Potentials: Significance and Applications inChemical Reactivity in Confined Systems pages\u2005113\u2013134 John Wiley & Sons Ltd2021.","DOI":"10.1002\/9781119683353.ch7"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.1706"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1326"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.25849"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.1c01269"},{"key":"e_1_2_8_73_1","unstructured":"W. Zou Y. Tao M. Freindorf M. Makos N. Verma E. Kraka LMODEA Computational and Theoretical Chemistry Group (CATCO) Southern Methodist University Dallas TX 2022."},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198406271"},{"key":"e_1_2_8_75_1","first-page":"1259","volume":"57","author":"Cremer Dieter","year":"1984","journal-title":"Croat. Chem. Acta"},{"key":"e_1_2_8_76_1","unstructured":"pandas development team pandas-dev\/pandas: Pandas2020 version\u20051.4.4; Zenodo (accessed February 2023)."},{"key":"e_1_2_8_77_1","doi-asserted-by":"crossref","unstructured":"W. McKinney Data Structures for Statistical Computing in Python in St\u00e9fan van der Walt Jarrod Millman (Editors) Proceedings of the 9th Python in Science Conference2010 pages\u200556\u201361.","DOI":"10.25080\/Majora-92bf1922-00a"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.21105\/joss.03021"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1109\/MCSE.2007.55"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.2307\/1412159"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1098\/rspl.1896.0076"}],"container-title":["ChemPhysChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cphc.202400607","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cphc.202400607","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T16:20:12Z","timestamp":1760372412000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cphc.202400607"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,3]]},"references-count":81,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2024,12,16]]}},"alternative-id":["10.1002\/cphc.202400607"],"URL":"https:\/\/doi.org\/10.1002\/cphc.202400607","archive":["Portico"],"relation":{},"ISSN":["1439-4235","1439-7641"],"issn-type":[{"value":"1439-4235","type":"print"},{"value":"1439-7641","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,3]]},"assertion":[{"value":"2024-05-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-03","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202400607"}}