A nuclear quadrupole resonance and X-ray study of the crystal structure of 2,5-dichloroaniline

Abstract

The crystal structure of 2,5-dichloroaniline, C6H3CleNH 2, has been determined by the combined application of nuclear quadrupole resonance and X-ray diffraction.The molecule is planar, except for the nitrogen which deviates slightly, by 0.06 A. The benzene ring is slightly deformed from the regular hexagon and the observed bond lengths agree well with the result of a simple molecular orbital calculation. There is no hydrogen bonding in the structure. The shortest intermolecular C1...C1 distance, 3.37 A, is shorter than the usually quoted van der Waals distance of 3.6 A.

The crystal structure of methyl orange monohydrate monoethanolate

“…The phenyl rings are inclined at about l0 ° to each other, a finding consistent with the spectroscopic indications for both the specimen material and the protein complex (Carey et al, 1972). Organic anion: The distribution of bond lengths in the aniline end of the anion is consistent with observations of aniline derivatives (Sakurai, Sundaralingam & Jeffrey, 1963;Trotter, Whitlow & Zobel, 1966). Thus C(10)-N(3) is much shorter than a single bond, and N(2)-C(7), while longer than C(10)-N(3), is significantly shorter than C(4)-N(1).…”

The crystal structure of 1-(2,6-dichlorobenzyl)-6-hydroxy-1,4,5,6-tetrahydronicotinamide dihydrate

“…The two C-C1 distances are observed to be slightly, and probably insignificantly, longer than the value 1.74 • found for other C(aromatic)-Cl distances (Sakurai, Sundaralingam & Jeffrey, 1963;Palenik, Donohue & Trueblood, 1968). (It is to be hoped that a value of about 1.74 ~ will soon gain access to compilations of bond distances, rather than the remarkably persistent value of 1.71 A listed for the standard C(arom)-Cl distance; e.g.…”

The crystal and molecular structure ofN,N-dimethyl-p-nitroaniline

“…Study of a number of nitro derivatives indicates that the C-N bond distances are all about 1.48 A (Trotter, 1960), not significantly different from the single-bond length; this can be accounted for in terms of valencebond theory by assuming (plausibly) that 'sacrificial' structures (such as (II) for nitrobenzene, which is sacrificial relative to (I) since it has one less double bond) make no, or relatively little, contribution to the resonance hybrid molecule (Sakurai, Sundaralingam & Jeffrey, 1963). The carbon-carbon bond length variations are then explicable in terms of differences in hybridization of the carbon a orbitals (other explanations might of course equally well be advanced).…”