Vacuum ultraviolet absorption studies of model sugar compounds Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/js956k91r

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  • Vacuum ultraviolet absorption spectra of 13 model sugar compounds were measured in the energy range of 50 to 80 kK. The model sugars included three simple alcohols, four simple ethers, four cyclic alcohol-ether compounds, and two dioxanes. All spectra show transition bands in the energy region 50 to 65 kK. When the model sugar spectra were compared to those for similar hydrocarbons, it was shown that the low energy transitions depend on the presence of the oxygen atom within the molecule. The question arose whether these transitions were due to σ - σ* transitions from CO or OH bonds or from non-bonding electrons on the oxygen. This was resolved by an independent systems calculation of the σ - σ* transitions for several of the model sugar compounds. The isolated bond transition energies for the series of bonds CH, OH, NH and CC, CN, CO and CF were calculated both by the extended Huckel method and by the complete neglect of differential overlap (CNDO) method. Five separate calculations were performed including one completely empirical CNDO calculation. Experimental results for hydrocarbons and fluorocarbons indicated that the completely empirical method was the best approximation. The results of an independent systems calculation for the model sugar compounds showed that the low energy transitions were not σ - σ* transitions. Therefore we concluded that they must be nonbonding oxygen transitions. The spectra of simple alcohols and ethers were then combined to predict spectra of the more complex model sugars and of glucose.
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