Tetrahedron p. 17425 - 17440 (1997)
Update date:2022-08-05
Topics:
Skar, Merete L.
Svendsen, John S.
The dibenzofuran-based diamide 4,6-bis(N-acyl-aminomethyl)dibenzofuran is shown by 1H NMR and IR to have favourable geometry for intramolecular hydrogen bonding. The corresponding dibenzothiophene-based diamide 4,6-bis(N-acyl-aminomethyl)dibenzothiophene does not fulfill the geometric requirements for intramolecular hydrogen bonding. The intramolecularly hydrogen bonded state of the dibenzofuran-based diamide la is found to be 1 ± 0.5 kcal/mol more favoured enthalpically and 4 ± 2 cal/(K·mol) disfavoured entropically than the non-hydrogen bonded state.
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