Jf. Liebman et Eh. Morkved, PARADIGMS AND PARADOXES - RESONANCE IN AROMATIC AND HETEROAROMATIC O-DICARBOXYLIC ACIDS, THEIR ANHYDRIDES AND IMIDES, Structural chemistry, 6(3), 1995, pp. 207-209
It is found that o-dicarboxylic acids derived from pyrrole and 1,2,5-t
hiadiazole do not form cyclic anhydrides as readily as phthalic acid.
This is discussed in terms of ionic resonance structures and derived s
tabilization of the anhydrides and acids.