2-Chloro-4-nitrobenzoic (2Cl4NBA) and 2-chloro-5-nitrobenzoic acids (2Cl5NBA) are antiviral agents used recently as potential drugs for the treatment of immunodeficiency diseases including HIV infections [1]. This study presents the synthesis and single crystal X-ray diffraction of new molecular salts of 2Cl4NBA and 2Cl5NBA with triethanolamine (TEA) in 1 : 1 molar ratio. Triethanolamine plays a promising role in crystal engineering by its ability to establish strong and directional hydrogen bonds because of number of potential donor sites of high electronegativity [2]. Herein, the role of hydrogen bonds in the packing of crystal structures was studied for one 2Cl4NBA salt (1) and for two polimorphic forms (2) and (3) of 2Cl5NBA salt. Analysis of the crystal structures of the reported polymorphs (2) and (3) reveals that one crystallizes in monoclinic P21/n space group, while the other in orthorhombic Pbcn space group. In 1 – 3 the acid protons have been transferred to the TEA nitrogen and the organic cations form R22(11) graph set with 4-nitrobenzoate anions due to O–H···O and charge-assisted O–H···O– H-bonds. All supramolecular architectures of studied compounds form hydrogen-bonded chains (1 and 3) and layer (2), dominated by O–H···O hydrogen bonds in 1 – 3, and additional N+–H···O in 2. The neighbor supramolecular arrays are further stabilized via C‒H···O hydrogen bonds in 2 and weak π‒π stacking interactions between adjacent phenyl rings in 3 form supramolecular layer (3) and network (2) structures.