{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,12]],"date-time":"2026-07-12T10:30:12Z","timestamp":1783852212936,"version":"3.55.0"},"reference-count":66,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2005,8,11]],"date-time":"2005-08-11T00:00:00Z","timestamp":1123718400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2005,11,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Zeolites are suitable microporous hosts for positively charged organic species, but it is believed that they cannot adsorb organic anions. Pure Meisenheimer complex, derived from reduction of 2,4\u2010dinitroaniline with NaBH<jats:sub>4<\/jats:sub>, was adsorbed inside faujasite cavities. Evidence for the internal incorporation of this negatively charged reaction intermediate comes from 1) XPS elemental analysis as a function of the depth of penetration into the particle, 2) the remarkable blue shift in <jats:italic>\u03bb<\/jats:italic><jats:sub>max<\/jats:sub> of the Meisenheimer complex adsorbed on zeolite (ca. 470 nm) as compared to that in acetonitrile (580 nm) and 3) from the lack of reactivity with size\u2010excluded hydride\u2010acceptor reagents. Evidence is provided in support of an adsorption mechanism in which a neutral ion pair (alkali metal ion+Meisenheimer anion) is the actual species being adsorbed. In fact it appears that there is remarkable increase in the association constant for the ion\u2010pair complex within the zeolite cavities as compared to DMF solution. Although this mechanism of adsorption as an ion\u2010pair complex has precedents in the adsorption of some inorganic salts, what is novel is the notable increase in the stability and persistence of the Meisenheimer anion (a anionic reaction intermediate) as a result of zeolite inclusion. Adsorbed Meisenheimer complex exhibits much lower reactivity towards electron acceptors, oxygen, and water. Cyclic voltammetry of zeolite\u2010modified electrodes reveals for the Meisenheimer complex adsorbed on LiY a reversible redox peak that is not observed in solution and has been interpreted as arising from site isolation and stabilisation of the electrochemically generated species.<\/jats:p>","DOI":"10.1002\/chem.200500125","type":"journal-article","created":{"date-parts":[[2005,8,11]],"date-time":"2005-08-11T08:55:39Z","timestamp":1123750539000},"page":"6491-6502","source":"Crossref","is-referenced-by-count":6,"title":["Anionic Organic Guests Incorporated in Zeolites: Adsorption and Reactivity of a Meisenheimer Complex in Faujasites"],"prefix":"10.1002","volume":"11","author":[{"given":"Jos\u00e9 Raul","family":"Herance","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patricia","family":"Concepci\u00f3n","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Dom\u00e9nech","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Luis","family":"Bourdelande","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jordi","family":"Marquet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hermenegildo","family":"Garc\u00eda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2005,10,26]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/a908408h"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr980026x"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1019118507128"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00004a057"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9702536"},{"key":"e_1_2_6_6_2","first-page":"2003","author":"Zhang G.","journal-title":"J. Phys. Chem. B"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b205672k"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/B206735H"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp020454d"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp021276r"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo020141e"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020402)114:7<1289::AID-ANGE1289>3.0.CO;2-A"},{"key":"e_1_2_6_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020402)41:7<1241::AID-ANIE1241>3.0.CO;2-C"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/la011414o"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp0113883"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp015518j"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp0116757"},{"key":"e_1_2_6_17_2","volume-title":"Zeolite Molecular Sieves: Structure, Chemistry and Use","author":"Breck D. W.","year":"1974"},{"key":"e_1_2_6_18_2","volume-title":"Zeolites and Clay Minerals as Sorbents and Molecular Sieves","author":"Barrer R. M.","year":"1978"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-2991(08)61559-1"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00209a057"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1557\/PROC-807-359"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.366611"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00057a002"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100156a059"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja962645y"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00227a062"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/a704920j"},{"key":"e_1_2_6_28_2","first-page":"9769","author":"Lee G. S.","journal-title":"J. Am. Chem. Soc. 2001 123"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100172a002"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1997.875"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/a902187f"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(94)00114-6"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(93)85622-U"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100083a022"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/B205953C"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp002480m"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a001"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470319543.ch7"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470066775.ch7"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00048a001"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50124a004"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/b207168a"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010417)7:8<1759::AID-CHEM17590>3.0.CO;2-F"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29830001197"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29800000243"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.19813140611"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-4095(200006)12:13<985::AID-ADMA985>3.0.CO;2-#"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1006\/jcis.2000.6777"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/ft9969201985"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)96237-5"},{"key":"e_1_2_6_51_2","volume-title":"Introduction to Zeolite Science and Practice","author":"Bekkum H. van","year":"1991"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100162a063"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00017a015"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100018a042"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)00410-8"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo030158c"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo025898k"},{"key":"e_1_2_6_58_2","first-page":"2350","author":"Parnes A. N.","year":"1971","journal-title":"Izv. Akad. Nauk SSSR Ser. Khim."},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00806a017"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00148a026"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9603259"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9603259"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/0013-4686(93)85072-7"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0144-2449(05)80057-0"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-88071-1"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200500125","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200500125","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T22:18:10Z","timestamp":1760307490000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200500125"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,10,26]]},"references-count":66,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2005,11,4]]}},"alternative-id":["10.1002\/chem.200500125"],"URL":"https:\/\/doi.org\/10.1002\/chem.200500125","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,10,26]]}}}