Isolation and X-ray Structural Characterization of a Dicationic Homotrimer of 2,3,6,7-tetramethoxy-9,10-dimethylanthracene cation radical

Authors

Matthew J. Modjewski, Marquette University
Ruchi Shukla, Marquette University
Sergey Lindeman, Marquette UniversityFollow
Rajendra Rathore, Marquette University

Document Type

Article

Language

eng

Format of Original

4 p.

Publication Date

12-2-2009

Publisher

Elsevier

Source Publication

Tetrahedron Letters

Source ISSN

0040-4039

Abstract

Electrochemical oxidation of 2,3,6,7-tetramethoxy-9,10-dimethylanthracene (1) showed that it undergoes a highly reversible electrochemical oxidation (E_ox = 0.81 V vs SCE) and forms a modestly stable cation-radical salt in solution. X-ray crystallography established that 1⁺SbCl₆^- crystallizes as a (centrosymmetric) dicationic homotrimer via a close cofacial association of a pair of cationic and one neutral molecule of 1 with an interplanar separation of ∼3.2 Å. The structure of the dicationic homotrimer was also reproduced by DFT calculations. Furthermore, the structure of a dicationic spiro adduct, formed by a slow decomposition of a solution of 1⁺SbCl₆^- was also established by X-ray crystallography.

Comments

Accepted version. Tetrahedron Letters, Vol. 50, No. 48 (December 2, 2009): 6687-6690. DOI. © 2009 Elsevier. Used with permission.

Recommended Citation

Modjewski, Matthew J.; Shukla, Ruchi; Lindeman, Sergey; and Rathore, Rajendra, "Isolation and X-ray Structural Characterization of a Dicationic Homotrimer of 2,3,6,7-tetramethoxy-9,10-dimethylanthracene cation radical" (2009). Chemistry Faculty Research and Publications. 544.
https://epublications.marquette.edu/chem_fac/544