[eng] Complexes between several anions (or lone pair donor molecules) and fluorinated tropolones have been optimized at the RI-MP2/aug-cc-pVDZ level of theory. It has been recently demonstrated [J. Med. Chem. 54 (2011) 4462] that a-hydroxytropolone and manicol (5,7-dihydroxy-2-isopropenyl-9-methyl-1,2,3,4- tetrahydro-benzocyclohepten-6-one) are potent and specific inhibitors of the ribonuclease H activity of human immunodeficiency virus reverse transcriptase in vitro. In the active site a lone pair-p interaction between a nitrogen atom of His539 amino acid and the tropolone ring is established. In this study we demonstrate that both lone pair-p and anion-p complexes are energetically favorable in two tropolone derivatives. The interaction has been characterized by means of the Bader's theory of ''atoms-inmolecules''.