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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.

Why do ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate and its analogues stay as Z-isomers only ?