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Substituent and Medium Effects on Nitrogen-15 Shieldings of Compounds with >C=N Bonds (Imines, Oximes, and Phenylhydrazones)

Westerman, Philip W. and Botto, Robert E. and Roberts, John D. (1978) Substituent and Medium Effects on Nitrogen-15 Shieldings of Compounds with >C=N Bonds (Imines, Oximes, and Phenylhydrazones). Journal of Organic Chemistry, 43 (13). pp. 2590-2596. ISSN 0022-3263. doi:10.1021/jo00407a009.

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The ^(15)N chemical shifts of ^(13)N -(arylmethylidene)alkanamines, seven N-(arylmethylidene)azanols, five 1-(aryImethylidene)- 2-phenyldiazanes, and 11 N-(arylmethylidene)arenamines have been determined at the natural abundance level of ^(15)N in several solvents. The shifts of several of the N-(phenylmethylidene)alkanamines with different alkane groups have been analyzed in terms of α-,β- and y-methyl substituent effects. For those N-(arylmethylidene) azanes substituted at the para position, linear correlations with Hammett σ parameters having negative slopes are found for the ^(15)N chemical shifts. However, the ^(15)N shifts of N-(phenylmethylidene)arenamines (substituted at the para position of the arenamine moiety) are essentially insensitive to the nature of the substituent. The slopes of the Hammett correlations become more negative with increasing proton-donating power of the solvent for most series of compounds studied. In general, the ^(15)N shifts were found to be 5-12 ppm toward higher fields in methanol compared to chloroform, and except for the alkylidenazanols (oximes), about the same in dimethyl sulfoxide as in chloroform. In contrast, the alkylidenazanol resonances move 13-16 ppm downfield for the change from chloroform to dimethyl sulfoxide.

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Additional Information:© 1978 American Chemical Society. Received September 2, 1977. Supported by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences, and by the National Science Foundation.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5663
Issue or Number:13
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Official Citation:Substituent and medium effects on nitrogen-15 shieldings of compounds with > C = N bonds (imines, oximes, and phenylhydrazones) Philip W. Westerman, Robert E. Botto, and John D. Roberts The Journal of Organic Chemistry 1978 43 (13), 2590-2596 DOI: 10.1021/jo00407a009
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60886
Deposited By: Ruth Sustaita
Deposited On:08 Oct 2015 18:31
Last Modified:10 Nov 2021 22:41

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