Abstract
13C, 15N and 17O NMR chemical shifts have been determined for 1-ethyl-2-pyrrolidinone neat and in some hydrogen bonding and non-hydrogen bonding solvents. Since hydrogen bond formation occurs with the oxygen atom of the carbamoyl group of 1-ethyl-2-pyrrolidinone, the sensitivity of the chemical shifts to the solvent decreases for these nuclei in the order 17O >15N >13C. Hydrogen bond forming solvents change the NMR chemical shifts to lower frequencies for the 17O nucleus and to higher frequencies for the 15N and 13C nuclei, reflecting the change in the double bond character between the nitrogen and carbon atoms of the amide.The changes observed in the chemical shifts seem primarily to depend on the hydrogen bond interactions of 1-ethyl-2-pyrrolidinone with the solvents; for the effect of the solvent on the chemical shifts of the nuclei of 1-ethyl-2-pyrrolidinone accords with the order of the hydrogen bonding and the polarity parameters of the solvents. The NMR chemical shift data for some 1-methyl-2-pyrrolidinone—solvent systems are also presented.
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