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Here, we confirm this phenomenon in four representative complexes, using state\u2010of\u2010the\u2010art quantum mechanical methods. By employing the block\u2010localized wavefunction (BLW) method, which can turn off intermolecular charge transfer interactions, we profoundly demonstrated the significance of charge transfer interactions in these seemingly counterintuitive complexes. Indeed, after being \u201cturned off\u201d the intermolecular charge transfer interaction in, for example, the FNSi\u00b7\u00b7\u00b7BrF complex, the originally attractive intermolecular interaction turns to be repulsive. The energy decomposition approach based on the BLW method (BLW\u2010ED) can partition the overall stability gained on the formation of intermolecular noncovalent interaction into several physically meaningful components. According to the BLW\u2010ED analysis, the electrostatic repulsion in these counterintuitive cases is overwhelmed by the stabilizing polarization, dispersion interaction, and most importantly, the charge transfer interaction, resulting in the eventual counterintuitive overall attraction. The present study suggests that, predicting bonding sites of noncovalent interactions using only the \u201chole\u201d concept may be not universally sufficient, because other significant stabilizing factors will contribute to the stability and sometimes, play even bigger roles than the electrostatic interaction and consequently govern the complex structures. \u00a9 2018 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/jcc.25566","type":"journal-article","created":{"date-parts":[[2018,10,5]],"date-time":"2018-10-05T19:19:51Z","timestamp":1538767191000},"page":"1015-1022","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Attraction between electrophilic caps: A counterintuitive case of noncovalent interactions"],"prefix":"10.1002","volume":"40","author":[{"given":"Changwei","family":"Wang","sequence":"first","affiliation":[{"name":"School of Chemistry &amp; Chemical Engineering Shaanxi Normal University  Xi'an 710119 China"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8730-5119","authenticated-orcid":false,"given":"David","family":"Danovich","sequence":"additional","affiliation":[{"name":"Institute of Chemistry The Hebrew University  Jerusalem 91904 Israel"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7643-9421","authenticated-orcid":false,"given":"Sason","family":"Shaik","sequence":"additional","affiliation":[{"name":"Institute of Chemistry The Hebrew University  Jerusalem 91904 Israel"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6139-5443","authenticated-orcid":false,"given":"Wei","family":"Wu","sequence":"additional","affiliation":[{"name":"Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering Xiamen University  Xiamen 360015 China"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2994-7754","authenticated-orcid":false,"given":"Yirong","family":"Mo","sequence":"additional","affiliation":[{"name":"Department of Chemistry Western Michigan University  Kalamazoo Michigan 49008"}]}],"member":"311","published-online":{"date-parts":[[2018,10,3]]},"reference":[{"key":"e_1_2_6_1_1","volume-title":"Non\u2010Covalent Interactions: Theory and Experiment","author":"Pavel H.","year":"2009"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030070z"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature08173"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nbt874"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007560"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030645s"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar0400995"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1162215"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c004189k"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct700216w"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct400185f"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2011.07.043"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.21352"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002146"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3562209"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1139\/v98-080"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200304891"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja056827g"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405812"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.25068"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01249"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar50116a004"},{"key":"e_1_2_6_23_1","volume-title":"The Nature of the Chemical Bond","author":"Pauling L. 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