SYNTHESIS AND STUDY OF PSEUDOAROMATIC COMPOUNDS .9. A REEVALUATION OF QUESTION OF AROMATIC CHARACTER IN TROPONES BASED ON DATA DERIVED FROM DIPOLE MOMENT MEASUREMENTS AND CNDO-2 CALCULATIONS

An analysis of the dipole moments of several unsaturated ketones and aldehydes in conjunction with CNDO/2 molecular orbital calculations is presented. In general this theory is shown to calculate dipole moments of ketones and aldehydes very well, and in conjunction with other experimental evidence leads to the conclusion that the dipolar character of tropones and tropolones has been greatly overestimated and that the ground states of these systems are adequately described as polyolefinic. © 1969, American Chemical Society. All rights reserved.