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Effects of Protonation and Hydrogen Bonding on Nitrogen-15 Chemical Shifts of Compounds Containing the >C:N-Group

Allen, Malwina and Roberts, John D. (1980) Effects of Protonation and Hydrogen Bonding on Nitrogen-15 Chemical Shifts of Compounds Containing the >C:N-Group. Journal of Organic Chemistry, 45 (1). pp. 130-135. ISSN 0022-3263. doi:10.1021/jo01289a025.

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The effects of solvent changes from chloroform to trifluoroethanol to trifluoroacetic acid on the chemical shifts of nitrogen-15 resonances have been determined for fourteen imines, four oximes, and two pyridines. Upfield shifts were observed for all of the compounds in trifluoroethanol and trifluoroacetic acid, ranging from 8 to 28 ppm in the first and from 110 to 150 ppm in the second. These shift changes can be attributed to hydrogen bonding and protonation, respectively. The hydrogen-bonding shifts can be generally rationalized through consideration of the basicities of the nitrogens involved while the protonation shifts seem mostly influenced by the degree of substitution by phenyl groups, as expected from changes in the substantial contributions to the >C=N- type nitrogen shifts from the second-order paramagnetic effect.

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Additional Information:© 1980 American Chemical Society. Received April 18, 1979. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry6007
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Official Citation:Effects of protonation and hydrogen bonding on nitrogen-15 chemical shifts of compounds containing the >C:N-Group Malwina Allen and John D. Roberts The Journal of Organic Chemistry 1980 45 (1), 130-135 DOI: 10.1021/jo01289a025
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60836
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 15:05
Last Modified:10 Nov 2021 22:40

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