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Steric modification of the intramolecular hydrogen bond in 2-(methylimino-phenyl-methyl)-phenols.
Autorzy
Rok wydania
1999
Czasopismo
Numer woluminu
130
Strony
1097-1108
DOI
10.1007/PL00010288
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Three ortho-hydroxy Schiff bases (2-(methylimino-phenyl-methyl)-phenol (1), 4-methyl-2-(methylimino-phenyl-methyl)-phenol (2), 2-(benzylimino-phenyl-methyl)-phenol (3)) weresynthesized in which the hydrogen atom in the C±C(H)=N group was substituted by a phenylring. Their crystal structures were determined. Strong O±H N type intramolecular hydrogen bondswere found (dON2.496(2) A Ê , dOH1.11(3) A Ê , dHN1.45(4) A Ê and dON2.488(2) A Ê , dOH1.20(4) A Ê , dHN1.37(4) A Ê in 1; dON2.505(2) A Ê , dOH1.16(3) A Ê , dHN1.39(3) A Ê in 2;dON2.528(2) A Ê , dOH1.08(3) A Ê , dHN1.54(4) A Ê in 3 together with a large proton delocalization,especially in 1 and 2. It was demonstrated that the strengthening of the hydrogen bond in comparisonto related non substituted compounds results from the steric repulsion exerted by the phenyl ring.
Adres publiczny
https://doi.org/10.1007/PL00010288
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