Paper
The crystal and molecule structure of three 2,4,6-trinitrobenzene derivatives:α,α,α-trifluoro-2,4,6-trinitrotoluene (C7H2F3N3O6), 2,4,6-trinitrobenzamide (C7H4N4O7), 2,4,6-trinitrobenzoic acid (C7H3N3O8)
Published Feb 1, 1989 · A. Rheingold, C. Baldacchini, C. Grote
Journal of Crystallographic and Spectroscopic Research
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Abstract
The crystal and molecular structures of three 2,4,6-trinitrobenzene derivatives have been determined. Forα,α,α-trifluoro-2,4,6-trinitrotoluene (1): monoclinic,P21/n,a=7.510(2),b=9.273(2),c=14.984(0) Å,β=99.02(2)°,V=1028.1(4)° Å3,Z=4,D=1.816 g cm−3,R(F)=0.051, andR(wF)=0.055. For 2,4,6-trinitrobenzamide (2): orthorhombic,Pbca,a=9.248(3),b=14.377(6),c=17.729(4) Å,V=1958(1) Å3,Z=8,D=1.737 g cm−3,R(F)=0.073, andR(wF)=0.077. For 2,4,6-trinitrobenzoic acid (3): orthorhombic,P212121,a=6.553(1),b=11.405(2),c=12.796(2) Å,V=956.3(3) Å3,Z=4,D=1.785 g cm−3,R(F)=0.045, andR(wF)=0.046.1 crystallizes as discrete molecules,2 as weakly hydrogen-bonded dimers and3 as a chiral polymer of hydrogen-bonded helices. In1, the presence of the nonplanar CF3 substituent causes a large twisting of theα-nitro groups out of the plane of the benzene ring, whereas the nearly planar C(O)NH2 and C(O)OH substituents in2 and3 are perpendicular to the benzene plane and do not cause a significant rotation of theα-nitro groups.
The crystal and molecular structures of three 2,4,6-trinitrobenzene derivatives reveal differences in substituent effects on -nitro groups, with CF3 substituent causing large twisting in 1, while nearly planar C(O)NH2 and C(O)OH substituents do not significantly affect rotation
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