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

Kuang-Sen Sung, Robert Sung, Michael Sung, Bo Ren Zhuang

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)137-147
Number of pages11
JournalArkivoc
Volume2006
Issue number11
Publication statusPublished - 2006 Jun 27

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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