ANTIAROMATICITY IN RELATION TO 1,3,5,7-CYCLOOCTATETRAENE STRUCTURES Academic Article uri icon

abstract

  • An isodesmic energy analysis has been carried out at the MP2/631G*//HF/321G level for the nonplanar ground state (1) of 1,3,5,7cyclooctateraene and for two planar forms, one having complete delocalization (2) and the other having alternating single and double bonds (3). 1 is found to have a considerable degree of stabilization, which is attributed to limited delocalization. The polyene 3 is the more stable of the two planar forms; it is a transition state in the inversion between two possible nonplanar structures. 2 is found to be a triplet at the HartreeFock level and is a critical point on an alternate pathway between the two possible arrangements of alternating single and double bonds in 3. Both 2 and 3 have negative isodesmic energies, indicating the presence of stabilizing factors. Our results for 3 show that an antiaromatic system need not necessarily show a net destabilization. 1994 John Wiley & Sons, Inc. Copyright 1994 John Wiley & Sons, Inc.

published proceedings

  • INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY

author list (cited authors)

  • POLITZER, P., MURRAY, J. S., & SEMINARIO, J. M.

citation count

  • 13

complete list of authors

  • POLITZER, P||MURRAY, JS||SEMINARIO, JM

publication date

  • May 1994

publisher