Rethinking the Nature and Extent of Inductive Effects in Organic Compounds
6 affiliations
- 1Cardiff University
- 2School of Chemistry
- 3College of Science, Engineering and Environment
- 4University of Newcastle
- 5School of Science and Technology
- 6University of New England
Abstract
High Resolution Image Download MS PowerPoint Slide The inductive effect is generally taught as being transmitted through the σ-bond framework in organic molecules, diminishing with each bond. This historical position does not align with more recent studies, and we show that the inductive effect in neutral molecules is effectively limited to one bond. Evidence of onward transmission (e.g., 13 C NMR chemical shifts) should be viewed with scepticism. In charged species, where an electron-donating functional group is coupled with a suitably disposed electron-withdrawing substituent, the effect is transmitted over more bonds. These examples should be considered as polarizability rather than ‘purely’ inductive. Examples that are commonly described as a through-space field effect are better explained by polarizability/orbital perturbation. This work presents a more complete view of the inductive effect and its interface with polarizability.
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BibTeX
@article{elliott2026rethinking,
title = {{Rethinking the Nature and Extent of Inductive Effects in Organic Compounds}},
author = {Mark C. Elliott and Edwin C. Johnson and Kasimir P. Gregory and Colan E. Hughes},
journal = {Journal of Chemical Education},
year = {2026},
month = may,
doi = {10.1021/acs.jchemed.6c00141},
url = {https://doi.org/10.1021/acs.jchemed.6c00141},
note = {CC BY},
}
RIS
TY - JOUR
TI - Rethinking the Nature and Extent of Inductive Effects in Organic Compounds
AU - Mark C. Elliott
AU - Edwin C. Johnson
AU - Kasimir P. Gregory
AU - Colan E. Hughes
PY - 2026
DA - 2026/05/14
JO - Journal of Chemical Education
DO - 10.1021/acs.jchemed.6c00141
UR - https://doi.org/10.1021/acs.jchemed.6c00141
AB - High Resolution Image Download MS PowerPoint Slide The inductive effect is generally taught as being transmitted through the σ-bond framework in organic molecules, diminishing with each bond. This historical position does not align with more recent studies, and we show that the inductive effect in neutral molecules is effectively limited to one bond. Evidence of onward transmission (e.g., 13 C NMR chemical shifts) should be viewed with scepticism. In charged species, where an electron-donating functional group is coupled with a suitably disposed electron-withdrawing substituent, the effect is transmitted over more bonds. These examples should be considered as polarizability rather than ‘purely’ inductive. Examples that are commonly described as a through-space field effect are better explained by polarizability/orbital perturbation. This work presents a more complete view of the inductive effect and its interface with polarizability.
SN - 0021-9584
SN - 1938-1328
ER -