{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T00:46:47Z","timestamp":1782262007865,"version":"3.54.5"},"reference-count":53,"publisher":"American Chemical Society (ACS)","issue":"1","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2009,1,2]]},"DOI":"10.1021\/jo802131v","type":"journal-article","created":{"date-parts":[[2008,12,3]],"date-time":"2008-12-03T09:28:58Z","timestamp":1228296538000},"page":"58-63","source":"Crossref","is-referenced-by-count":72,"title":["The Acid Hydrolysis Mechanism of Acetals Catalyzed by a Supramolecular Assembly in Basic Solution"],"prefix":"10.1021","volume":"74","author":[{"given":"Michael D.","family":"Pluth","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of California, Berkeley, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California, 94720"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert G.","family":"Bergman","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of California, Berkeley, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California, 94720"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenneth N.","family":"Raymond","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of California, Berkeley, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California, 94720"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,12,2]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1039\/B710355G","author":"Das S.","year":"2008","journal-title":"Chem. Commun."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"5830","DOI":"10.1002\/anie.200702125","volume":"46","author":"Schmuck C.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1039\/B614961H","volume":"37","author":"Koblenz T. S.","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1016\/j.ccr.2007.10.010","volume":"252","author":"Dalgarno S. J.","year":"2008","journal-title":"Coord. Chem. Rev."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"2366","DOI":"10.1002\/anie.200602815","volume":"46","author":"Oshovsky G. V.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"3650","DOI":"10.1021\/ja973898+","volume":"120","author":"Kang J. M.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1038\/385050a0","volume":"385","author":"Kang J. M.","year":"1997","journal-title":"Nature"},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"7389","DOI":"10.1021\/ja980927n","volume":"120","author":"Kang J. M.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"7000","DOI":"10.1021\/ja071591x","volume":"129","author":"Nishioka Y.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"1445","DOI":"10.1021\/cr0300688","volume":"105","author":"Vriezema D. M.","year":"2005","journal-title":"Chem. Rev."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1351\/pac200577071107","volume":"77","author":"Yoshizawa M.","year":"2005","journal-title":"Pure Appl. Chem."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1126\/science.1124985","volume":"312","author":"Yoshizawa M.","year":"2006","journal-title":"Science"},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"8160","DOI":"10.1021\/ja802818t","volume":"130","author":"Nishioka Y.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"7810","DOI":"10.1021\/ja802288k","volume":"130","author":"Hou J.-L.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"4102","DOI":"10.1039\/b712529a","volume":"40","author":"Yamashita K.","year":"2007","journal-title":"Chem. Commun."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"6748","DOI":"10.1002\/anie.200461776","volume":"43","author":"Fiedler D.","year":"2004","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1126\/science.1138748","volume":"316","author":"Pluth M. D.","year":"2007","journal-title":"Science"},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1021\/ar020076v","volume":"37","author":"Cacciapaglia R.","year":"2004","journal-title":"Acc. Chem. Res."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"2450","DOI":"10.1021\/ja076162d","volume":"130","author":"Schramm M. P.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"5147","DOI":"10.1021\/ol701883u","volume":"9","author":"Ryu E.-H.","year":"2007","journal-title":"Org. Lett."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"2018","DOI":"10.1021\/jo026482+","volume":"68","author":"Krishnaveni N. S.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1002\/ejoc.200700954","volume":"4","author":"Bjerre J.","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1139\/v06-039","volume":"84","author":"Ortega-Caballero F.","year":"2006","journal-title":"Can. J. Chem."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"3238","DOI":"10.1021\/ja042678a","volume":"127","author":"Ortega-Caballero F.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"2734","DOI":"10.1002\/ejoc.200500034","volume":"13","author":"Rousseau C.","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"4590","DOI":"10.1002\/anie.200600812","volume":"45","author":"Marinescu L. G.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"8923","DOI":"10.1021\/ja0104507","volume":"123","author":"Caulder D. L.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"1840","DOI":"10.1002\/(SICI)1521-3773(19980803)37:13\/14<1840::AID-ANIE1840>3.0.CO;2-D","volume":"37","author":"Caulder D. L.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1039\/a808370c","volume":"8","author":"Caulder D. L.","year":"1999","journal-title":"J. Chem. Soc., Dalton. Trans."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"12094","DOI":"10.1021\/ja075236i","volume":"129","author":"Biros S. M.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"7912","DOI":"10.1021\/ja051037s","volume":"127","author":"Davis A. V.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"10240","DOI":"10.1021\/ja062329b","volume":"128","author":"Fiedler D.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"10977","DOI":"10.1021\/ja8013055","volume":"130","author":"Hastings C. J.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"11459","DOI":"10.1021\/ja072654e","volume":"129","author":"Pluth M. D.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"6362","DOI":"10.1021\/ja076691h","volume":"130","author":"Pluth M. D.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"11423","DOI":"10.1021\/ja802839v","volume":"30","author":"Pluth M. D.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"8587","DOI":"10.1002\/anie.200703371","volume":"46","author":"Pluth M. D.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"8989","DOI":"10.1016\/j.tet.2003.03.002","volume":"59","author":"Ates A.","year":"2003","journal-title":"Tetrahedron"},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1021\/jo016180s","volume":"67","author":"Carrigan M. D.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"9093","DOI":"10.1021\/jo0260387","volume":"67","author":"Dalpozzo R.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"8399","DOI":"10.1021\/jo001202g","volume":"65","author":"Eash K. J.","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"751","DOI":"10.3390\/71000751","volume":"7","author":"Mirjalili B. F.","year":"2002","journal-title":"Molecules"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"3207","DOI":"10.1002\/(SICI)1521-3773(19991102)38:21<3207::AID-ANIE3207>3.0.CO;2-I","volume":"38","author":"Marko I. E.","year":"1999","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref44\/cit44","unstructured":"The acetone product formed in the reaction is stable under the reaction conditions and does not undergo an aldol reaction to form mesityl oxide."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1021\/ar00006a001","volume":"24","author":"Breslow R.","year":"1991","journal-title":"Acc. Chem. Res."},{"key":"ref46\/cit46","unstructured":"In contrast to the solvent dependence observed for neutral guest encapsulation, we have previously shown that protonated guests are readily encapsulated in either aqueous or polar organic solvents (see refs 34, 35)."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","DOI":"10.1007\/978-1-4757-1592-7","volume-title":"The Proton in Chemistry","author":"Bell R. P.","year":"1973"},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/9780470171837.ch1","volume":"4","author":"Cordes E. H.","year":"1967","journal-title":"Prog. Phys. Org. Chem."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1021\/cr60291a004","volume":"74","author":"Cordes E. H.","year":"1974","journal-title":"Chem. Rev."},{"key":"ref50\/cit50","unstructured":"In basic D2O solution, the methyl hydrogens of the acetone product slowly undergo H\/D exchange with the solvent. However, under the time course of the reaction the rate of exchange is negligible. Furthermore, at the concentrations of the kinetic runs, complete H\/D exchange would form less than 1% of HDO and therefore has been ignored."},{"key":"ref51\/cit51","unstructured":"A-2 mechanisms are often accompanied by more negative entropies of activation that A-SE2 mechanisms. One possible explanation for the attenuated negative entropy of activation for the hydrolysis of2in1is that encapsulation of the substrate (and possibly water) in the interior cavity diminishes the entropic penalty generally associated with bringing the acetal and water molecules together. This hypothesis is consistent with previous mechanistic studies of the aza-Cope rearrangement in1in which the entropy of activation for reactions occurring in1was more positive than in free solution (see ref32,33)."},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"2294","DOI":"10.1021\/jo01282a604","volume":"32","author":"Pletcher T.","year":"1967","journal-title":"J. Org. Chem."},{"key":"ref53\/cit53","first-page":"319","volume":"46","author":"Ammann C.","year":"1982","journal-title":"J. Magn. Reson. A"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo802131v","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,4]],"date-time":"2024-03-04T02:49:51Z","timestamp":1709520591000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo802131v"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,12,2]]},"references-count":53,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2009,1,2]]}},"alternative-id":["10.1021\/jo802131v"],"URL":"https:\/\/doi.org\/10.1021\/jo802131v","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,12,2]]}}}