{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T03:50:41Z","timestamp":1775274641394,"version":"3.50.1"},"reference-count":71,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2020,1,30]],"date-time":"2020-01-30T00:00:00Z","timestamp":1580342400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP15H03817"],"award-info":[{"award-number":["JP15H03817"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP19H04585"],"award-info":[{"award-number":["JP19H04585"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP18J13703"],"award-info":[{"award-number":["JP18J13703"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009088","name":"Nippon Sheet Glass Foundation for Materials Science and Engineering","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100009088","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008656","name":"Iketani Science and Technology Foundation","doi-asserted-by":"publisher","award":["0311087-A"],"award-info":[{"award-number":["0311087-A"]}],"id":[{"id":"10.13039\/501100008656","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100008965","name":"Takahashi Industrial and Economic Research Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100008965","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,3,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Uncommon entropy\u2010driven cooperativity is reported in the guest binding of an octaphosphonate bis\u2010cavitand. Isothermal titration calorimetry determined the thermodynamic parameters for the 1:2 host\u2013guest binding of bis\u2010cavitands with ammonium guests in methanol, ethanol, 2\u2010propanol, and chloroform. Chloroform drove uncommon entropy\u2010driven cooperative binding, whereas the alcohols resulted in enthalpy\u2010driven noncooperative binding. <jats:sup>1<\/jats:sup>H\u2005NMR studies revealed that each cavity contained six water molecules in chloroform, which were liberated on guest binding. The enthalpy\u2013entropy compensation relationship produced a large positive intrinsic entropy in chloroform, which implies that water desolvation causes a considerable entropic gain by paying an enthalpic penalty due to breaking the hydrogen\u2010bonding networks of the water clusters.<\/jats:p>","DOI":"10.1002\/chem.201905036","type":"journal-article","created":{"date-parts":[[2019,12,5]],"date-time":"2019-12-05T08:56:39Z","timestamp":1575536199000},"page":"3074-3079","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Entropy\u2010Driven Cooperativity in the Guest Binding of an Octaphosphonate Bis\u2010cavitand"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7862-5188","authenticated-orcid":false,"given":"Daisuke","family":"Shimoyama","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hiroshima University  1-3-1 Kagamiyama Higashi-Hiroshima 739-8526 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0945-2893","authenticated-orcid":false,"given":"Takeharu","family":"Haino","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hiroshima University  1-3-1 Kagamiyama Higashi-Hiroshima 739-8526 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,1,30]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00141a001"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3.0.CO;2-3"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19981016)110:20<2908::AID-ANGE2908>3.0.CO;2-2"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300644"},{"key":"e_1_2_7_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300644"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio0808-435"},{"key":"e_1_2_7_6_1","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00103a006"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar000177y"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030673a"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.20153"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902490"},{"key":"e_1_2_7_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902490"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203814"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC00573K"},{"key":"e_1_2_7_14_1","unstructured":"\u00a0"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00311a043"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199011481"},{"key":"e_1_2_7_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19901021028"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.74.883"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/b108121g"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049336p"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900642"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5120437"},{"key":"e_1_2_7_22_1","unstructured":"\u00a0"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199702591"},{"key":"e_1_2_7_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971090329"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-00683-5"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611394"},{"key":"e_1_2_7_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201611394"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800997"},{"key":"e_1_2_7_27_1","unstructured":"\u00a0"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301996q"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02301"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01730"},{"key":"e_1_2_7_31_1","unstructured":"\u00a0"},{"key":"e_1_2_7_32_2","volume-title":"Container Molecules and Their Guests","author":"Cram D. J.","year":"1994"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199909)1999:9<1991::AID-EJOC1991>3.0.CO;2-5"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00191E"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00153B"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)02031-J"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1007\/b13779"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300430"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801002"},{"key":"e_1_2_7_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801002"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300178m"},{"key":"e_1_2_7_42_1","unstructured":"\u00a0"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201600410"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja210567k"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.langmuir.6b01709"},{"key":"e_1_2_7_46_1","unstructured":"\u00a0"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/b917931c"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201003407"},{"key":"e_1_2_7_49_1","unstructured":"\u00a0"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00913599"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04372"},{"key":"e_1_2_7_52_1","unstructured":"\u00a0"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800327"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CE01813C"},{"key":"e_1_2_7_55_1","unstructured":"\u00a0"},{"key":"e_1_2_7_56_2","volume-title":"Cation Binding by Macrocycles: Complexation of Cationic Species by Crown Ethers","author":"Inoue Y.","year":"1990"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00076a023"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/P29850000935"},{"key":"e_1_2_7_59_1","unstructured":"\u00a0"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310958"},{"key":"e_1_2_7_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201310958"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00583"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja407951x"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0146-0"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201905036","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201905036","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201905036","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201905036","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:43:23Z","timestamp":1760298203000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201905036"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,1,30]]},"references-count":71,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2020,3,9]]}},"alternative-id":["10.1002\/chem.201905036"],"URL":"https:\/\/doi.org\/10.1002\/chem.201905036","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,1,30]]},"assertion":[{"value":"2019-11-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-01-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}