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

Author:
Kazim, Muhammad, Siegler, Maxime A., Lectka, Thomas
Source:
Journal of organic chemistry 2019 v.84 no.12 pp. 8284-8288
ISSN:
1520-6904
Subject:
X-ray diffraction, aromatization, moieties, organic chemistry, protonation, quinones, spectroscopy
Abstract:
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.
Agid:
6478112