A Protonated Quinone Methide Stabilized by a Combination of Partial Aromatization and π‑Interaction: Spectroscopic and Crystallographic Analysis

We have expanded the repertoire of cation−π interactions to include a carbocation−π system resulting from the protonation of a π-stacked para-quinone methide (p-QM). This unusual carbocation is stabilized by a combination of partial aromatization of the QM moiety and through-space interaction with t...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 12; pp. 8284 - 8288
Main Authors Kazim, Muhammad, Siegler, Maxime A, Lectka, Thomas
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.06.2019
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Summary:We have expanded the repertoire of cation−π interactions to include a carbocation−π system resulting from the protonation of a π-stacked para-quinone methide (p-QM). This unusual carbocation is stabilized by a combination of partial aromatization of the QM moiety and through-space interaction with the π-system of the adjacent aromatic ring. Single crystal X-ray analysis of the protonated form reveals a structure consisting of a hydrogen-bound complex involving two molecules of the precursor and one proton.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00923