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^(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

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00794a041DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00794a041PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
Max Kade Foundation, Inc.UNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry4511
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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