
%0 Journal Article
%A Morgan, Joy L. 
%A Flood, Amar 
%A Gordon, Keith C. 
%A Kjaergaard, Henrik G. 
%A Robinson, Brian H. 
%A Simpson, Jim 
%T 2,6-Diazaanthracene-9,10-dione and its Radical Anion&#8212; A Structural and Spectroscopic Investigation
%J Australian Journal of Chemistry
%D 2003/06/13
%V 56
%N 6
%P 607-614
%K 
%R https://doi.org/10.1071/CH02238
%U https://www.publish.csiro.au/paper/CH02238 
%X An analysis of the structure, vibrational and electronic spectra, and the molecular orbitals of 2,6-diazaanthracene-9,10-dione (DAAD) (1) and its radical anion is presented. Strong &#960;-stacking is seen in the crystal structure of (1) and observed bond lengths and angles are in good agreement with those calculated with the B3LYP/6-31G(d) method. The vibrational spectra of (1) show strong bands at 1686 cm&#8211;1 (IR) and 1676 cm&#8211;1 (Raman) corresponding to the antisymmetric and symmetric C&equals;O stretch, respectively, in good agreement with calculated data. Electrochemical or chemical reduction to (1)&#8226;- results in a new spectrum with a strong absorption due to the antisymmetric stretch at 1481 cm&#8211;1 (predicted 1470 cm&#8211;1). The lowest energy electronic transition for (1) occurs at 317 nm; new transitions at lower energy (403, 573, and 910 nm) are seen in the spectrum of (1)&#8226;-. The dark purple radical anion (1)&#8226;- was isolated as the Cp2Co+ salt but its ESR spectrum did not display hyperfine coupling. 
