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Indole and N-methylindole have been partially or fully deuterated by Raney nickel catalyzed 1H-2H exchange in a series of deuterated solvents. Perdeuterated indoles have been obtained in water and methanol while compounds that are preferentially deuterated at specific sites were obtained in chloroform, acetone, acetonitrile, ethanol, and isopropanol. The partially deuterated compounds are an important research tool for solid-state NMR studies on proteins.
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Yau et al. (1999) studied this question.
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