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Carbon-13 nuclear magnetic resonance spectroscopy. Substituent-induced chemical shift effects on cyclopropyl carbons of 4-substituted cyclopropylbenzenes

Kusuyama, Yoshiaki and Dyllick-Brenzinger, Christina and Roberts, John D. (1980) Carbon-13 nuclear magnetic resonance spectroscopy. Substituent-induced chemical shift effects on cyclopropyl carbons of 4-substituted cyclopropylbenzenes. Organic Magnetic Resonance, 13 (5). pp. 372-375. ISSN 0030-4921. https://resolver.caltech.edu/CaltechAUTHORS:20151006-132045529

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Abstract

Carbon-13 chemical shifts of the cyclopropyl carbons of eleven 4-substituted cyclopropylbenzenes have been measured under conditions effectively corresponding to infinite dilution in DCCI_3. The substituent-induced chemical shifts (SCS) of both the α and β carbons of the cyclopropane ring were found to be downfield with electron-attracting groups and upfield for electron-donating groups. The trends for the β carbons correspond to those observed for the β carbons of 4-substituted phenylethenes, while the trends of the α carbons are similar to those found for the α carbons of 4-substituted isopropyl benzenes. The results for the β carbons can be rationalized by postulating a substantial contribution from a hyperconjugative resonance effect involving the σ system of the benzene ring (and its 4-substituent) and the C-α—C-β bonds of the cyclopropane ring. The effects on the α carbons are in accord with a very reasonable smaller inductive polarization of the C-α-C-β bonds than encountered for the carbons of corresponding ethenyl- or ethynylbenzenes.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/mrc.1270130516DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270130516/abstractPublisherArticle
Additional Information:© 1980 Heyden & Son Ltd. Received 20 March 1979; accepted (revised) 1 August 1979. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11073 from the Division of General Medical Sciences.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
NIHGM-11073
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Caltech Gates and Crellin Laboratories of Chemistry6060
Issue or Number:5
Record Number:CaltechAUTHORS:20151006-132045529
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151006-132045529
Official Citation:Kusuyama, Y., Dyllick-Brenzinger, C. and Roberts, J. D. (1980), Carbon-13 nuclear magnetic resonance spectroscopy. Substituent-induced chemical shift effects on cyclopropyl carbons of 4-substituted cyclopropylbenzenes. Org. Magn. Reson., 13: 372–375. doi: 10.1002/mrc.1270130516
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60810
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 16:23
Last Modified:03 Oct 2019 09:00

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