Story of the Pentamethyl-Cyclopentadienyl CationC5Me5+.ppt

Story of the Pentamethyl-Cyclopentadienyl CationC5Me5+ Roger L. DeKock Department of Chemistry and Biochemistry Calvin College, Grand Rapids, MI dekock@ The Stable Pentamethyl-cyclopentadienyl Cation Angewandte Chemie Int. Ed. 2002, 41, No. 8, 1429-1431, by Joseph B. Lambert, Lijun Lin, and Vitaly Rassolov. Antiaromatic, 2n Aromatic, 2n+2 The Stable Pentamethyl-cyclopentadienyl Cation “Elusive Carbocation Isolated as a Solid” Chemical and Engineering News, April 29, 2002. Four unusual features Stable Unequal C-C bond lengths around the ring Me-C-C-Me dihedral angle nearly 110° Singlet state, no unpaired spins The Fall-Out Corrigendum, Issue No. 10 Note from the Editors: unfortunately the results reported in the communication “The Stable Pentamethylcylopentadienyl Cation” by Joseph B. Lambert et al. in issue 8/2002 (pp. 1429-1431) must be corrected. Guy Bertrand et al. quickly discovered that not the pentamethyl-cylopentadienyl cation but pentamethyl-cylopentenyl cation was prepared ? The Fall-Out Editorial (Issue No. 13, page 2211) “And Hückel Was Correct After All―A Withdrawal and an Apology” by Dr. Peter G?litz, Editor “The Stable Pentamethylcyclopentdienyl Cation Remains Unknown”, by M. Otto, D. Scheschkewitz, T. Kato, M. M. Midland, J. B. Lambert, and G. Bertrand. Angewandte Chemie Int. Ed. 2002, 41, No. 13, 2275-2276. The Fall-Out “Comment on the X-Ray Structure of Pentamethylcyclopentadienyl Cation” by Thomas Müller, Angewandte Chemie Int. Ed. 2002, 41, No. 13, 2276-2278. “Statement” by Joseph B. Lambert, Angewandte Chemie Int. Ed. 2002, 41, No. 13, 2278. The Fall-Out “The crystal structure of ‘pentamethyl-cylopentadienyl cation’ is that of the pentamethylcyclopentyl cation” by Jamie N. Jones, Alan H. Cowley, and Charles L. B. Macdonald, Chemical Communications, 2002, 1520-1521. Connection to Pedagogy Two-week computational chemistry module in advanced organic chemistry and in biophysical chemistry Week 1 Before lab session students are given the o