{"id":"https://openalex.org/W2793166330","doi":"https://doi.org/10.1002/wcms.1113","title":"\u03c3\u2010Holes","display_name":"\u03c3\u2010Holes","publication_year":2012,"publication_date":"2012-08-08","ids":{"openalex":"https://openalex.org/W2793166330","doi":"https://doi.org/10.1002/wcms.1113","mag":"2793166330"},"language":"en","primary_location":{"id":"doi:10.1002/wcms.1113","doi":"https://doi.org/10.1002/wcms.1113","is_oa":false,"landing_page_url":"https://doi.org/10.1002/wcms.1113","pdf_url":null,"source":{"id":"https://openalex.org/S136120998","display_name":"Wiley Interdisciplinary Reviews Computational Molecular Science","issn_l":"1759-0876","issn":["1759-0876","1759-0884"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","ki-jl-1","norway-1","poland-200","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"WIREs Computational Molecular Science","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref"],"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/A5017203543","display_name":"Timothy Clark","orcid":"https://orcid.org/0000-0001-7931-4659","observed_orcids":["https://orcid.org/0000-0001-7931-4659"]},"institutions":[{"id":"https://openalex.org/I181369854","display_name":"Friedrich-Alexander-Universit\u00e4t Erlangen-N\u00fcrnberg","ror":"https://ror.org/00f7hpc57","country_code":"DE","type":"education","lineage":["https://openalex.org/I181369854"]},{"id":"https://openalex.org/I63072094","display_name":"University of Portsmouth","ror":"https://ror.org/03ykbk197","country_code":"GB","type":"education","lineage":["https://openalex.org/I63072094"]}],"countries":["DE","GB"],"is_corresponding":true,"raw_author_name":"Timothy Clark","raw_affiliation_strings":["Center for Molecular Design, University of Portsmouth, Portsmouth, United Kingdom","Computer-Chemie-Centrum der Friedrich-Alexander Universita\u0308t Erlangen-Nu\u0308rnberg, Erlangen, Germany","Computer-Chemie-Centrum der Friedrich-Alexander Universit\u00e4t Erlangen-N\u00fcrnberg, Erlangen, Germany"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Center for Molecular Design, University of Portsmouth, Portsmouth, United Kingdom","institution_ids":["https://openalex.org/I63072094"]},{"raw_affiliation_string":"Computer-Chemie-Centrum der Friedrich-Alexander Universita\u0308t Erlangen-Nu\u0308rnberg, Erlangen, Germany","institution_ids":["https://openalex.org/I181369854"]},{"raw_affiliation_string":"Computer-Chemie-Centrum der Friedrich-Alexander Universit\u00e4t Erlangen-N\u00fcrnberg, Erlangen, Germany","institution_ids":["https://openalex.org/I181369854"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5017203543"],"corresponding_institution_ids":["https://openalex.org/I181369854","https://openalex.org/I63072094"],"apc_list":{"value":5230,"currency":"USD","value_usd":5230},"apc_paid":null,"fwci":16.5949,"has_fulltext":false,"cited_by_count":288,"citation_normalized_percentile":{"value":0.99740002,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":98,"max":100},"biblio":{"volume":"3","issue":"1","first_page":"13","last_page":"20"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.9970999956130981,"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"}},"topics":[{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.9970999956130981,"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"}},{"id":"https://openalex.org/T10002","display_name":"Advanced Chemical Physics Studies","score":0.002300000051036477,"subfield":{"id":"https://openalex.org/subfields/3107","display_name":"Atomic and Molecular Physics, and Optics"},"field":{"id":"https://openalex.org/fields/31","display_name":"Physics and Astronomy"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12044","display_name":"Advanced Physical and Chemical Molecular Interactions","score":9.999999747378752e-05,"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/sigma-hole","display_name":"sigma-hole","score":0.765999972820282},{"id":"https://openalex.org/keywords/molecular-electrostatic-potential","display_name":"molecular electrostatic potential","score":0.9890000224113464},{"id":"https://openalex.org/keywords/noncovalent-interactions","display_name":"non-covalent interactions","score":0.8090000152587891},{"id":"https://openalex.org/keywords/halogen-bonding","display_name":"halogen bonding","score":0.9980000257492065},{"id":"https://openalex.org/keywords/hydrogen-bonding","display_name":"hydrogen bonding","score":0.8519999980926514},{"id":"https://openalex.org/keywords/net-atomic-charges","display_name":"net atomic charges","score":0.6299999952316284},{"id":"https://openalex.org/keywords/covalent-bonding","display_name":"covalent bonding","score":0.5809999704360962}],"concepts":[{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.7867398262023926},{"id":"https://openalex.org/C180577832","wikidata":"https://www.wikidata.org/wiki/Q127920","display_name":"Covalent bond","level":2,"score":0.747785210609436},{"id":"https://openalex.org/C159467904","wikidata":"https://www.wikidata.org/wiki/Q2001702","display_name":"Chemical physics","level":1,"score":0.6137396693229675},{"id":"https://openalex.org/C23029723","wikidata":"https://www.wikidata.org/wiki/Q1193318","display_name":"Halogen bond","level":4,"score":0.589542806148529},{"id":"https://openalex.org/C137277065","wikidata":"https://www.wikidata.org/wiki/Q2915446","display_name":"Non-covalent interactions","level":4,"score":0.5644794702529907},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5306113362312317},{"id":"https://openalex.org/C46062151","wikidata":"https://www.wikidata.org/wiki/Q19605","display_name":"Halogen","level":3,"score":0.5153378844261169},{"id":"https://openalex.org/C178213299","wikidata":"https://www.wikidata.org/wiki/Q44424","display_name":"Chemical bond","level":2,"score":0.46940720081329346},{"id":"https://openalex.org/C117626034","wikidata":"https://www.wikidata.org/wiki/Q26336","display_name":"Electrostatics","level":2,"score":0.4131203293800354},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.3822033703327179},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.33080214262008667},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.2541373372077942},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.0978999137878418},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.06542196869850159},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.057934969663619995}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/wcms.1113","doi":"https://doi.org/10.1002/wcms.1113","is_oa":false,"landing_page_url":"https://doi.org/10.1002/wcms.1113","pdf_url":null,"source":{"id":"https://openalex.org/S136120998","display_name":"Wiley Interdisciplinary Reviews Computational Molecular Science","issn_l":"1759-0876","issn":["1759-0876","1759-0884"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","ki-jl-1","norway-1","poland-200","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"WIREs Computational Molecular Science","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"sustainable_development_goals_aurora":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":51,"referenced_works":["https://openalex.org/W655715115","https://openalex.org/W1548914255","https://openalex.org/W1964004579","https://openalex.org/W1971413830","https://openalex.org/W1972398130","https://openalex.org/W1972764077","https://openalex.org/W1982572408","https://openalex.org/W1988069288","https://openalex.org/W1989333060","https://openalex.org/W1990449537","https://openalex.org/W1992525635","https://openalex.org/W1999765807","https://openalex.org/W2004052472","https://openalex.org/W2006728016","https://openalex.org/W2009516314","https://openalex.org/W2016285581","https://openalex.org/W2018398804","https://openalex.org/W2021650034","https://openalex.org/W2023629397","https://openalex.org/W2025878283","https://openalex.org/W2026598007","https://openalex.org/W2027638954","https://openalex.org/W2036867140","https://openalex.org/W2038767330","https://openalex.org/W2041302869","https://openalex.org/W2042375039","https://openalex.org/W2043798058","https://openalex.org/W2045382844","https://openalex.org/W2046853706","https://openalex.org/W2047364144","https://openalex.org/W2049281887","https://openalex.org/W2050890227","https://openalex.org/W2052512097","https://openalex.org/W2054975178","https://openalex.org/W2063779505","https://openalex.org/W2065243431","https://openalex.org/W2070914359","https://openalex.org/W2074239340","https://openalex.org/W2078641649","https://openalex.org/W2078952998","https://openalex.org/W2085647917","https://openalex.org/W2090247989","https://openalex.org/W2093880244","https://openalex.org/W2094294679","https://openalex.org/W2131214655","https://openalex.org/W2132760463","https://openalex.org/W2159356452","https://openalex.org/W2166344128","https://openalex.org/W2317057295","https://openalex.org/W2323510144","https://openalex.org/W4233998925"],"related_works":["https://openalex.org/W2004052472","https://openalex.org/W1625726308","https://openalex.org/W1041901","https://openalex.org/W1002860447","https://openalex.org/W2063200470","https://openalex.org/W2006728016","https://openalex.org/W2080130231","https://openalex.org/W2065485112","https://openalex.org/W2016373164","https://openalex.org/W2018398804"],"abstract_inverted_index":{"Abstract":[0],"\u03c3\u2010Holes":[1,33],"are":[2,22],"regions":[3],"of":[4,18,47,57,97,106,122],"positive":[5,84],"molecular":[6],"electrostatic":[7],"potential":[8],"collinear":[9],"with":[10],"and":[11,83,125,144],"opposite":[12],"to":[13,16],"covalent":[14],"bonds":[15,124,128],"atoms":[17,37,67],"Groups":[19],"IV\u2013VII.":[20],"They":[21],"responsible":[23],"for":[24],"many":[25,64],"noncovalent":[26],"bonding":[27,49,88],"interactions,":[28],"such":[29,118],"as":[30,39,93,119],"halogen":[31],"bonding.":[32],"make":[34],"\u2018negatively":[35],"charged\u2019":[36],"act":[38],"if":[40],"they":[41,77],"were":[42],"\u2018positively":[43],"charged\u2019.":[44],"The":[45],"existence":[46],"\u03c3\u2010hole":[48,98,108,136],"emphasizes":[50],"what":[51],"has":[52],"been":[53],"called":[54],"\u2018the":[55],"fallacy":[56],"net":[58],"atomic":[59],"charges\u2019,":[60],"which":[61],"means":[62],"that":[63],"covalently":[65],"bonded":[66],"cannot":[68],"be":[69,91,130],"represented":[70],"adequately":[71],"by":[72],"a":[73,94],"single":[74],"charge":[75],"because":[76],"look":[78],"negative":[79],"from":[80,85],"some":[81],"directions":[82],"others.":[86],"Hydrogen":[87],"can":[89,129],"also":[90],"regarded":[92],"special":[95],"case":[96,103],"bonding,":[99],"although":[100],"in":[101,113],"this":[102],"the":[104,107,114,120,135],"origin":[105],"is":[109,140],"rationalized":[110],"differently":[111],"than":[112],"heavier":[115],"elements.":[116],"Phenomena":[117],"directionality":[121],"hydrogen":[123,127],"\u2018blue\u2010shifted\u2019":[126],"explained":[131],"very":[132],"simply":[133],"using":[134],"concept.":[137],"This":[138],"article":[139],"categorized":[141],"under:":[142],"Structure":[143],"Mechanism":[145],">":[146],"Molecular":[147],"Structures":[148]},"counts_by_year":[{"year":2026,"cited_by_count":16},{"year":2025,"cited_by_count":17},{"year":2024,"cited_by_count":9},{"year":2023,"cited_by_count":6},{"year":2022,"cited_by_count":12},{"year":2021,"cited_by_count":25},{"year":2020,"cited_by_count":16},{"year":2019,"cited_by_count":22},{"year":2018,"cited_by_count":21},{"year":2017,"cited_by_count":38},{"year":2016,"cited_by_count":27},{"year":2015,"cited_by_count":32},{"year":2014,"cited_by_count":24},{"year":2013,"cited_by_count":18},{"year":2012,"cited_by_count":5}],"updated_date":"2026-10-08T09:06:37.294493","created_date":"2018-03-29T00:00:00"}