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A method benchmark was performed on 2\u2010bromo\u20101\n                    <jats:italic>H<\/jats:italic>\n                    \u2010imidazol\u20103\u2010ium in association with chloride (\n                    <jats:bold>1\u2010Br\u22c5Cl<\/jats:bold>\n                    ); MP2 yielded the best results when compared with CCSD(T) calculations. The interaction energies (\u0394\n                    <jats:italic>E<\/jats:italic>\n                    ) in the gas phase are high and, although the electrostatic interaction is strong owing to the ion\u2010pair nature of the system, large X\u22c5\u22c5\u22c5Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    Wiberg bond orders and contributions from charge transfer (n\n                    <jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/asia201601690-math-0001.png\" xlink:title=\"urn:x-wiley:18614728:media:asia201601690:asia201601690-math-0001\"\/>\n                    \u2192\u03c3*C\u2212X) are obtained. These values drop considerably in chloroform and water; this shows that solvent plays a role in modulating the interaction and that gas\u2010phase calculations are particularly unrealistic for experimental applications. The introduction of electron\u2010withdrawing groups in the 4,5\u2010positions of the imidazolium (e.g., \u2212NO\n                    <jats:sub>2<\/jats:sub>\n                    , \u2212F) increases the halogen\u2010bond strength in both the gas phase and solvent, including water. The effect of the substituents on the 1,3\u2010positions (N\u2212H groups) also depends on the solvent. The variation of \u0394\n                    <jats:italic>E<\/jats:italic>\n                    can be predicted through a two\u2010parameter linear regression that optimizes the weights of charge\u2010transfer and electrostatic interactions, which are different in vacuum and in solvent (chloroform and water). These results could be used in the rational design of efficient chloride receptors based on halogen bonds that work in solution, in particular, in an aqueous environment.\n                  <\/jats:p>","DOI":"10.1002\/asia.201601690","type":"journal-article","created":{"date-parts":[[2017,1,3]],"date-time":"2017-01-03T13:36:18Z","timestamp":1483450578000},"page":"586-594","source":"Crossref","is-referenced-by-count":15,"title":["Ion\u2010Pair Halogen Bonds in 2\u2010Halo\u2010Functionalized Imidazolium Chloride Receptors: Substituent and Solvent Effects"],"prefix":"10.1002","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9014-0570","authenticated-orcid":false,"given":"Rafael","family":"Nunes","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, DQB Faculdade de Ci\u00eancias da Universidade de Lisboa, Campo Grande  1749-016 Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0492-6666","authenticated-orcid":false,"given":"Paulo J.","family":"Costa","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, DQB Faculdade de Ci\u00eancias da Universidade de Lisboa, Campo Grande  1749-016 Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,2,3]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/JS8631600239"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-006-0130-2"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1113"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/open.201100015"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1189"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2010.01.022"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct500422t"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300577"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CP05220J"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800128"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800128"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc03347b"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35213C"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC03638D"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001729"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001729"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108404"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108404"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja302213r"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300464"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300464"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2111"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504018"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201604327"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201604327"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2011.02.027"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.comptc.2012.02.036"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cp44649b"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg3015578"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/qua.21369"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2007.11.037"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp110295n"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.4748264"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-012-1114-1"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2011.03.085"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp503436f"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp506663x"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(68)88057-3"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA13988K"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201501921"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.5b09738"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201501149"},{"key":"e_1_2_6_40_1","unstructured":"\u00a0"},{"key":"e_1_2_6_41_2","volume-title":"Ion 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Nonetheless WI could also be used as a measure of the covalent nature of the halogen bond. 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