Wydział Chemii

Aleksander Filarowski

Aleksander Koll

Tadeusz Głowiak

2002

Journal of the Chemical Society-Perkin Transactions 2: Physical Organic Chemistry

835-842

10.1039/B106145N

Naukowa

Angielski

Artykuł

Five derivatives of an ortho-hydroxy Schiff base (2-(N-alkyl-α-iminoethyl)phenols) with very short intramolecular hydrogen bonds (d_O(H)⋯N ≤ 2.500 Å) were synthesised. The crystal structures were determined. The steric repulsion of the substituted methyl group results in an unusual strengthening of the hydrogen bonds, decreasing the barrier for the proton movement within the hydrogen bridge, which leads to a delocalization of the proton position. The very strong influence of the character of the substituent in the phenol ring as well as the character of the N-alkyl chain on the proton distribution is demonstrated for these hydrogen bonds from the so-called inversion range.

DOI https://doi.org/10.1039/B106145N

https://www.rsc.org/