Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations.
[structure: see text] (1)H NMR measurements and ab initio calculations were used to study the interactions between hindered/nonhindered phenols and carboxylic acid esters. The dihedral angle (phi) between the OH group and a plane of the aromatic ring is close to 0 degrees in the hydrogen-bonded nonhindered phenols, whereas for 2,6-di-tert-butyl-4-methylphenol the OH group is completely twisted out of the aromatic plane (phi approximately 90 degrees ).
Litwinienko
Grzegorz
G
Warsaw University, Department of Chemistry, Pasteura 1, 02-093 Warsaw, Poland. grzegorz.litwinieko@nrc.ca
Megiel
Elzbieta
E
Wojnicz
Marcin
M
D000975:Antioxidants / Q000737:chemistry*; D002084:Butylated Hydroxytoluene / Q000737:chemistry; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry*
D000975:Antioxidants; D004952:Esters; D005227:Fatty Acids; D007202:Indicators and Reagents; D010636:Phenols; D002084:Butylated Hydroxytoluene