Christl, Manfred and Warren, John P. and Hawkins, Bruce L. and Roberts, John D. (1973) ^(13)C and ^(15)N Nuclear Magnetic Resonance Spectroscopy of Nitrile Oxides and Related Reaction Products. Unexpected ^(13)C and ^(15)N Nuclear Magnetic Resonance Parameters of 2,4,6-Trimethylbenzonitrile Oxide. Journal of the American Chemical Society, 95 (13). pp. 4392-4397. ISSN 0002-7863. doi:10.1021/ja00794a041. https://resolver.caltech.edu/CaltechAUTHORS:20151009-133522523
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Abstract
The ^(13)C nmr spectra of several aryl nitrile oxides have been taken. The magnitude of ^1J^_(C(13)-^(15)N) for 2,4,6-trimethylbenzonitrile-^(15)N has been found to be 77.5 Hz, by far the largest one-bond carbon-nitrogen spin-spin coupling constant yet reported. The ^(13)C resonance of the carbon atom bonded to the nitrogen atom in this nitrile oxide is considerably shifted upfield by comparison with the analogous ^(13)C resonances of nitriles; however, little change is seen in the paramagnetic shielding term for ^(15)N upon conversion of a nitrile to a nitrile oxide. The ^(13)C and ^(15)N spectra are reported for a precursor and some reaction products of 2,4,6-trimethylbenzonitrile-^(15)N oxide. The low-field position of the ^(15)N resonances of isoxazole systems is discussed in relation to nitrogen chemical shifts for other five-membered heterocycles.
Item Type: | Article | |||||||||
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Alternate Title: | Carbon-13 and nitrogen-15 nuclear magnetic resonance spectroscopy of nitrile oxides and related reaction products. Unexpected carbon-13 and nitrogen-15 nuclear magnetic resonance parameters of 2,4,6-trimethylbenzonitrile oxide | |||||||||
Additional Information: | © 1973 American Chemical Society. Received July 21, 1972. Supported by the National Science Foundation and the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences; Max Kade Foundation, Inc., Fellow, 1970-1971. | |||||||||
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Issue or Number: | 13 | |||||||||
DOI: | 10.1021/ja00794a041 | |||||||||
Record Number: | CaltechAUTHORS:20151009-133522523 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151009-133522523 | |||||||||
Official Citation: | Carbon-13 and nitrogen-15 nuclear magnetic resonance spectroscopy of nitrile oxides and related reaction products. Unexpected carbon-13 and nitrogen-15 nuclear magnetic resonance parameters of 2,4,6-trimethylbenzonitrile oxide Manfred Christl, John P. Warren, Bruce L. Hawkins, and John D. Roberts Journal of the American Chemical Society 1973 95 (13), 4392-4397 DOI: 10.1021/ja00794a041 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 60942 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Ruth Sustaita | |||||||||
Deposited On: | 16 Oct 2015 01:35 | |||||||||
Last Modified: | 10 Nov 2021 22:42 |
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