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Examination of the Matrix Isolation Fourier Transform Infrared Spectra of Organic Compounds: Part X

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The characteristics of the OH stretching absorptions in a series of catechols, resorcinols, hydroquinones, and diols have been documented with the use of matrix isolation Fourier transform infrared spectroscopy. Steric and electronic effects were described and found to agree with published results on the vapor-phase studies on the same compounds. The positions of the OH absorptions were shown to fall within a window set on the high energy side by the vapor-phase results and on the lower energy side by solid-state/solution results. The very low full width at half-height values unique to the matrix experiment allowed for the observance of absorption bands not yet seen before in the vapor-phase or solid-state studies. These new bands confirm the presence of intramolecular interactions not previously documented. The data as a whole do indicate that extensive intermolecular interactions do occur at very low loadings on the cryogenic disk (10 ng) for compounds containing polar substituents.

Keywords: Catechols; Diols; Hydrogen bonding; Hydroquinones; Infrared; Matrix isolation; Resorcinols

Document Type: Research Article


Affiliations: R. J. Reynolds Tobacco Company, Bowman Gray Technical Center, Winston-Salem, North Carolina 27102

Publication date: May 1, 1988

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