Density functional method and isodesmic reactions were used to explore relative stability between Z- and E-ethyl [2-cyano-3-(n-butylamino)acryloyl] carbamate (3). Hydrogen bonding stabilization (7.19 kcal/mol) in favor of Z-3 and both steric hindrance (2.17 kcal/mol) and resonance stabilization (1.79 kcal/mol) in favor of E-3 contribute the relative stability between Z-3 and E-3, and that successfully explains why 3 stay as a Z-isomer only.
|Number of pages||11|
|Publication status||Published - 2006 Jun 27|
All Science Journal Classification (ASJC) codes
- Organic Chemistry