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Methyl Substitution as a Probe for π‐Spin Distribution in the Radical Anion of 1,6‐Methano[10]annulene
Author(s) -
Gerson Fabian,
Müllen Klaus,
Wydler Christoph
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590442
Subject(s) - annulene , chemistry , hyperfine structure , derivative (finance) , ion , planarity testing , spin (aerodynamics) , naphthalene , spectral line , photochemistry , substitution (logic) , radical ion , proton , medicinal chemistry , computational chemistry , crystallography , atomic physics , organic chemistry , quantum mechanics , aerospace engineering , programming language , computer science , physics , financial economics , engineering , economics
ESR. and ENDOR. spectra are reported for the radical anion of the 2‐methyl derivative (III) of 1,6‐methano[10]annulene (I). Comparison of the hyperfine data for I·⊖ and III·⊖ with those for the radical anions of naphthalene (II) and its 1‐methyl derivative (IV), respectively, confirms the suggestion that – despite the vastly different α‐proton coupling constants – the π‐spin distributions should be similar in the two series. This result provides further support for the view that the π‐spin distribution, in particular, and the cyclic π‐delocalisation, in general, are not seriously perturbed by moderate deviations of the π‐perimeter from planarity.