Publication costs assisted by Lebanon Valley CollegeThe hydrogen bonding of phenol, guaiacol, and catechol to the electron pair donors, dimethyl sulfoxide, tetrahydrofuran, and di-nbutyl sulfide, was studied in CCU solution at various temperatures by monitoring the hydroxyl stretching frequency at 3 µ. Only dimethyl sulfoxide was found to disrupt the intramolecular hydrogen bond of guaiacol. The intramolecular bond strength for guaiacol was found to be -3.3 kcal mol-1. All donors disrupt the intramolecular bond in catechol with consequent formation of hydrogen bonded complexes containing one and two donor molecules. The frequency shifts and enthalpy changes for the formation of the monodonor complex with catechol are larger than the corresponding properties for the phenol complex and reflect the influence of the intramolecular hydrogen bond on intermolecular hydrogen bonding.
Quick, Edward Edwards, "The interaction and reactivity of nitric oxide and carbon monoxide on ruthenium surfaces " (1979
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