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Inne
Anomalous strengthening of the intramolecular hydrogen bond by steric repulsion.
Autorzy
Rok wydania
1997
Czasopismo
Journal of Molecular Structure
Numer woluminu
404
Strony
67-74
DOI
10.1016/S0022-2860(96)09363-5
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The crystal structures of two ortho-aminomethylphenols, the 4,5-dimethyl- and 3,5,6-trimethyl-2(N,N-dimethylaminomethyl) phenols, were determined. The stronger intramolecular hydrogen bond was found in the compound with the higher number of methyl substituents. This result was supported by IR spectra. The atomic charge distribution calculated by the MNDO-PM3 method predicts higher strengths of the hydrogen bond in 4,5-dimethyl-2(N,N-dimethylaminomethyl) phenol molecules. Both theoretical calculations and crystallographic results explain the observed effects with reference to the steric interaction of the ortho methyl group which squeezes the OHtctdot;N hydrogen bridge.
Słowa kluczowe
Hydrogen bonding, Ortho-aminophenols, Steric repulsion, X-ray crystallography
Adres publiczny
https://doi.org/10.1016/S0022-2860(96)09363-5
Strona internetowa wydawcy
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