Hydrogen Bonding in Acid Li-, Ni-, Tetrabutylammonium, and Ammonium Salts of Benzene-1,2,4,5-tetracarboxylic Acid (Pyromellitic Acid)

Document Type

Article

Publication Date

8-1-1992

Abstract

Four acid salts of pyromellitic acid (benzene-1,2,4,5-tetracarboxylic acid) have been synthesized and studied by X-ray diffraction and IR spectroscopy. (1) Dilithium dihydrogen pyromellitate pentahydrate, Li2[C6H2(COO)4H2]·5 H2O; monoclinic, P21/m, a = 6.214(2), b = 19.647(7), c = 6.592(2)Å, β = 115.90(2)°, Z = 2, R = 0.068, Rw = 0.067. (2) Hexaaquanickel dihydrogen pyromellitate, [Ni(H2O)6][C6H2(COO)4H2]; monoclinic, P2/m, a = 6.528(1), b = 9.927(2), c = 6.472(1)Å, β = 115.57(1)°, Z = 1, R = 0.044, Rw = 0.039. (3) Tetrabutylammonium trihydrogen pyromellitate, [(C4H9)4N][C6H2(COO)4H3]; monoclinic, P21/c, a = 9.719(4), b = 18.823(8), c = 15.795(5)Å, β = 107.42(3)°, Z = 4, R = 0.059, Rw = 0.039. (4) Diammonium dihydrogen pyromellitate, [NH4]2[C6H2(COO)4H2]; monoclinic, P21/c, a = 4.7665(6), b = 11.681(3), c = 10.149(2)Å, β = 102.19(2)°, Z = 2, R = 0.045, Rw = 0.039. Compounds 1, 2, and 3 show very short intramolecular hydrogen bonds between adjacent carboxylic groups (O…O distances 2.384(6), 2.386(5), 2.387(3)Å, respectively). Compound 4 forms intermolecular hydrogen bonds (O…O distance 2.642(2)Å). The different hydrogen bonding modes are also evident in the IR spectra. © 1992, Walter de Gruyter. All rights reserved.

Publication Title

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

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