Charge density distribution in acrolein, butadiene and vinylamine unimportance of dipolar resonance structures in determining the ground state charge distribution

✍ Scribed by Kenneth B. Wiberg; Robert E. Rosenberg

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 273 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93833-x

✦ Synopsis

The charge distributions in acrolein, butadiene and vinylamine have been calculated from 6-31G** wave functions.

A comparison of the distributions at the vinyl group for the planar and 90" rotated forms indicated no significant charge shift. A comparison between butadiene and the other compounds again indicated no significant differences. It is concluded that the dipolar structures do not contribute significantly to the ground state structures, but rather they might best be considered as indicators of the easiest mode of charge polarization in the presence of an attacking reagent. %a-Unsaturated carbonyl compounds and enamines have received extensive synthetic utilization because of their high reactivity. The reactivity has generally been ascribed to changes in charge distribution arising from the dipolar resonance structures: l No -+m"-