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Crystal and Electronic Structures of Hydrogen-Bonded 2,5-Diamino-3,6-dihydroxy-p-benzoquinone

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journal contribution
posted on 04.01.2006, 00:00 by Tomoyuki Akutagawa, Takayoshi Nakamura
Shiny green-colored single crystals of 2,5-diamino-3,6-dihydroxy-p-benzoquinone (1) were prepared from 2,3,5,6-tetrahydroxy-p-phenylenediammonium dichloride. X-ray crystal structural analysis and ab initio calculations revealed that the molecular structure of 1, a highly polarized zwitterionic structure, was similar to that of p-benzoquinone rather than that of p-quinodiimine. Furthermore, a regular π-stack and an intermolecular two-dimensional hydrogen-bonding network were observed within the crystals of 1. The green color in the solid state was attributable to the intermolecular charge-transfer interactions.