Add time:07/15/2019         Source:sciencedirect.com

Cocrystallization experiments of the commonly available 4-aminobenzoic acid(L1)/2-aminobenzoic acid(L2), with a series of organic acids gave a total of five molecular salts with the compositions: (4-aminobenzoic acid): (dichloroacetic acid)2 (1) [(HL1)+ · (dca−) · (Hdca), dca− = dichloroacetate, Hdca = dichloroacetic acid], (4-aminobenzoic acid): (trichloroacetic acid) (2) [(HL1)+ · (tca−), tca− = trichloroacetate], (2-aminobenzoic acid): (trichloroacetic acid) (3) [(HL2)+ · (tca−)], (2-aminobenzoic acid): (3-nitrophthalic acid): H2O (4) [(HL2)+ ·· (Hnpa−) · H2O, Hnpa− = 3-nitrohydrogenphthalate], and (4-aminobenzoic acid)2: (1, 5-naphthalenedisulfonic acid) (5) [(HL1)22+ · (nds2−), nds2− = 1,5-naphthalenedisulfonate]. The structures of these salts were subsequently characterized by IR, elemental analysis, and X-ray diffraction analysis technique and the melting points of all the salts were also reported.In the five salts, the NH2 of the aminobenzoic acids are protonated when the organic acids are deprotonated, and the crystal packing is interpreted in terms of strong NH⋯O hydrogen bonds between the ammonium and deprotonated acidic groups. Except the NH⋯O H-bond, the OH⋯O H-bonds were also found at 1–5.In 4–5 only supramolecular heterosynthons were found, 1–3 had both homo and heterosynthons. These supramolecular synthons exhibit R12(5), R12(3), R21(6), R22(4), R22(5), R22(6), R22(8), R22(10), R32(7), R33(10), R33(11), R42(8), and R42(16) ring motifs. These motifs could have important function in the formation and stabilization of the crystals. Further inspection into the crystal packing of the salts indicated that a large variety of different secondary interactions were also existed in 1–5, which contribute to the stabilization and expansion of the total 2D-3D frameworks.

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