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The benzylideneacetone\u2010derived phenyl hydrazone is chosen as model substrate for the cyclization reaction, both in the protonated (A<\/jats:bold>) and unprotonated (B<\/jats:bold>) form, while the isoelectronic carbon analogue, 1,5\u2010diphenylpentadienyl anion (C<\/jats:bold>), serves as a reference for comparisons. The barrier to cyclization is computed to be more than 15 kcal\/mol lower in A<\/jats:bold> compared with B<\/jats:bold>, in line with the observed acid catalysis. The relevant transition states to cyclization are characterized for A<\/jats:bold> and C<\/jats:bold> using orbital inspection, natural bond orbital analysis, nucleus independent chemical shifts, and stereochemical indicators. The cyclization of C<\/jats:bold> is confirmed to be pericyclic, while that of A<\/jats:bold> can be described as pseudopericyclic ring closure involving an intramolecular nucleophilic addition. \u00a9 2015 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/jcc.24044","type":"journal-article","created":{"date-parts":[[2015,9,16]],"date-time":"2015-09-16T09:34:30Z","timestamp":1442396070000},"page":"280-285","source":"Crossref","is-referenced-by-count":9,"title":["Cyclization of an \u03b1<\/i>,\u03b2<\/i>\u2010Unsaturated hydrazone catalyzed by a BINOL\u2010phosphoric acid: Pericyclic or not?"],"prefix":"10.1002","volume":"37","author":[{"given":"Berit","family":"Heggen","sequence":"first","affiliation":[{"name":"Max\u2010Planck\u2010Institut f\u00fcr Kohlenforschung Kaiser\u2010Wilhelm\u2010Platz 1 45470 M\u00fclheim an der Ruhr Germany"}]},{"given":"Mahendra","family":"Patil","sequence":"additional","affiliation":[{"name":"Centre for Excellence in Basic Sciences Health Centre, University of Mumbai Vidhyanagaria Campus Mumbai 400098 India"}]},{"given":"Walter","family":"Thiel","sequence":"additional","affiliation":[{"name":"Max\u2010Planck\u2010Institut f\u00fcr Kohlenforschung Kaiser\u2010Wilhelm\u2010Platz 1 45470 M\u00fclheim an der Ruhr Germany"}]}],"member":"311","published-online":{"date-parts":[[2015,9,16]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/b807577h"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200700415"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100348t"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205343"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905035"},{"key":"e_1_2_6_6_1","first-page":"2171","volume":"13","author":"M\u00fcller S.","year":"2010","journal-title":"Synthesis"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15022g"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407677"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301638"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408020"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470148136"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja960582d"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030088"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00430a060"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010202)40:3<557::AID-ANIE557>3.0.CO;2-T"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200390211"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1674902"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.447079"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja017559z"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00072a001"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_6_24_1","volume-title":"Gaussian 09, Rev. 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