2-[(trifluoroacetyl)amino]benzoquinone and the hydrochloride and perchlorate salts of 2-aminohydroquinone

Abstract

Hydrogen bonding parameters for the title materials are reported. 2-[(trifluoroacetyl)amino]benzoquinone crystallizes in the monoclinic space group P2 ₁/c, with a = 18.195(4), b = 5.110(1), c = 9.635(2), β = 104.22(3)°, V = 868.4(3) ų, and Z = 4. This compound exhibits two weak intramolecular hydrogen bonds. The first is between a hydrogen atom of the quinone ring and the carbonyl oxygen of the trifluoroacetamide group; it has a distance of 2.24 Å and a C—H⋅⋅⋅sO angle of 122°. The second is between the hydrogen atom of the trifluoroacetamide group and a quinone carbonyl group; it has a distance of 2.26 Å and a N—H⋅⋅⋅sO angle of 107°. 2-Aminohydroquinone hydrochloride crystallizes in the orthorhombic space group Pca2₁, with a = 16.220(3), b = 5.211(1), c = 8.719(2), V = 737.0(2) ų, and Z = 4. 2-Aminohydroquinone perchlorate crystallizes in the orthorhombic space group P2₁2₁2₁, with a = 7.110(1), b = 7.139(1), c = 18.043(4), V = 915.8(3) ų, and Z = 4. All active hydrogens of the two salts exhibit intermolecular hydrogen bonds that serve to organize a three-dimensional framework for each case.