Transmission of substituent effects via molecular lines of force: defense of the DSP method and an illustration of its use in explaining pi polarization

Craik, D. J., Brownlee, R. and Sadek, M. (1982) Transmission of substituent effects via molecular lines of force: defense of the DSP method and an illustration of its use in explaining pi polarization. Journal of Organic Chemistry, 47 4: 657-661. doi:10.1021/jo00343a011


Author Craik, D. J.
Brownlee, R.
Sadek, M.
Title Transmission of substituent effects via molecular lines of force: defense of the DSP method and an illustration of its use in explaining pi polarization
Formatted title
Transmission of substituent effects via molecular lines of force: Defense of the DSP method and an illustration of its use in explaining π polarization
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
1520-6904
Publication date 1982
Sub-type Article (original research)
DOI 10.1021/jo00343a011
Volume 47
Issue 4
Start page 657
End page 661
Total pages 5
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
This paper disputes the conclusions of a recent report by Laszlo and co-workers33 regarding the applicability of the dual substituent parameter (DSP) method to studies of substituent effects on 13C chemical shifts. We show that the ρI and ρR transmission coefficients obtained from DSP analyses of 13C shifts in side chains of styrene derivatives provide useful mechanistic information. Trends in chemical shifts for a number of C=O or C=N probe groups are discussed and interpreted in terms of the π-polarization mechanism. The concept that π-polarization effects may be partially transmitted via "molecular lines of force" is introduced and compared with the classical through-space transmission mode of polarization effects. The interrelationship between this concept and that of extended polarization is discussed.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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