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Radical cations of disubstituted cyclopropanes: stereoelectronic effects on hyperfine coupling
Author(s) -
Roth Heinz D.,
Sauers Ronald R.,
Theisen Kevin J.,
Neshchadin Dmytro,
Gescheidt Georg
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3269
Subject(s) - chemistry , geminal , cidnp , hyperfine coupling , hyperfine structure , coupling constant , computational chemistry , medicinal chemistry , stereochemistry , radical , organic chemistry , atomic physics , physics , particle physics
The positive hyperfine coupling constants of the geminal 1 H nuclei in cis ‐1,2‐dimethyl‐ and cis ‐1,2‐diphenylcyclopropane radical cations show a significant stereoelectronic effect: the 1 H nuclei trans ( anti ) to the substituents are coupled much more strongly than the corresponding nuclei cis ( syn ) to them. Theoretical calculations on these radical cations and on bismethano[2,2]paracylophane as well as new 1 H‐CIDNP experiments at 200 Mz elucidate the general features of these systems. Copyright © 2014 John Wiley & Sons, Ltd.