4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, 4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine and N,N'-bis(2,4-dinitrophenyl)octane-1,8-diamine.
4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, C(22)H(38)N(4)O(4), (I), 4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine, C(28)H(50)N(4)O(4), (II), and N,N'-bis(2,4-dinitrophenyl)octane-1,8-diamine, C(20)H(24)N(6)O(8), (III), are the first synthetic meta-dinitroarenes functionalized with long-chain aliphatic amine groups to be structurally characterized. The intra- and intermolecular interactions in these model compounds provide information that can be used to help understand the physical properties of corresponding polymers with similar functionalities. Compounds (I) and (II) possess near-mirror symmetry, with the octyl and undecyl chains adopting fully extended anti conformations in the same direction with respect to the ring. Compound (III) rests on a center of inversion that occupies the mid-point of the central C-C bond of the octyl chain. The middle six C atoms of the chain form an anti arrangement, while the remaining two C atoms take hard turns almost perpendicular to the rest of the chain. All three molecules display intramolecular N-H...O hydrogen bonds between the amine and nitro groups, with the same NH group forming a bifurcated intermolecular hydrogen bond to the nitro O atom of an adjacent molecule. In each case, these interactions link the molecules into one-dimensional molecular chains. In (I) and (II), these chains pack so that the pendant alkyl groups are interleaved parallel to one another, maximizing nonbonded C-H contacts. In (III), the alkyl groups are more isolated within the molecular chains and the primary nonbonded contacts between the chains appear to involve the nitro groups not involved in the hydrogen bonding.
Teng
Gary
G
Department of Chemistry, Central Michigan University, Mount Pleasant, MI 48859, USA.
Walczak
Christopher P
CP
Squattrito
Philip J
PJ
Mohanty
Dillip K
DK
Scharer
William
W
Giolando
Mark R
MR
Kirschbaum
Kristin
K