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Qualitative comparison of peptide-bond isosteres.
| Hydrogen bond | n→π* interaction | |||||
|---|---|---|---|---|---|---|
| Isostere | Dipole moment |
cis-trans rigidity |
donor | acceptor | donor | acceptor |
| amide | 0 | 0 | 0 | 0 | 0 | 0 |
| thioamide | + | + | + | − | + | − |
| ester | − | − | − | − | + | |
| alkene | − − | + + | − − | − | ||
| fluoroalkene | − | + + | − | − | − | − |
