A three-dimensional refinement of the crystal structure of 4-nitroaniline

Trueblood, K. N.; Goldish, Elihu; Donohue, Jerry

doi:10.1107/s0365110x61002965

Cited by 200 publications

(108 citation statements)

References 2 publications

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“…Similar features appear in the temperature parameters of o~-TMA (Duchamp & Marsh, 1969), hemimellitic acid dihydrate (Mo & Adman, 1975) and isophthalic acid (Alcala & Martinez-Carrera, 1972). The enhanced displacement amplitudes of the carboxyl O atoms could well be due to libration of the carboxyl groups about the C(ring)-C(carboxyl) bonds, as was invoked to explain the large vibration amplitudes of O atoms in nitro groups (Trueblood, Goldish & Donohue, 1961 ;Dunitz & White, 1973); the displacement amplitudes of the water molecules could represent simple out-of-plane vibrations, since all of the restraining hydrogen bonds lie in-plane.…”

Section: Molecular Dimensionsmentioning

confidence: 60%

The crystal structures of trimesic acid, its hydrates and complexes. II. Trimesic acid monohydrate–2/9 picric acid and trimesic acid 5/6 hydrate

Herbstein¹,

Marsh²

1977

Acta Crystallogr Sect B

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(Mo Ka', 2840 and 6768 non-zero reflections respectively). In TMA. H20.~PA there are hydrogen-bonded layers of-composition TMA .H20 in the (i i 1) planes; these layers are pierced by channels along [001] containing the picric acid molecules. Diffuse X-ray scattering by these crystals suggests that the enclathrated pictic acid molecules have only a short-range coherence with the TMA .HzO layers. TMA.5H2 O contains very similar layers of TMA. HzO in the (100) planes; the five such layers in the [I00] repeat are offset such that the channel takes on a zigzag shape in order to accommodate zigzag ribbons of TMA molecules (two per cell), hydrogen bonded through the carboxyl groups in the 1-and 3-positions. The enclathrated TMA molecules are strictly ordered with respect to the TMA. H20 framework. Introduction ExperimentalWe report here the crystal structures of two hydrates of trimesic acid (TMA) that were uncovered during a survey of TMA compounds. The two structures are similar, both being based on a planar framework of hydrogen-bonded TMA and water molecules, with the planar arrays stacked so as to form channels containing guest molecules. In one structure, with empirical formula TMA.]H20, the channels are occupied by additional TMA molecules in an ordered array; in the other, TMA.H20.~-PA (PA = picric acid), the PA molecules occupy the channels in a disordered fashion. Both structures are somewhat unusual. TMA.~H20 contains 12 molecules of TMA and 10 water molecules per unit cell, in space group P1; in the picric acid complex, the chain of PA molecules has a different periodicity from the host framework, leading to additional, diffuse layer lines. Accordingly, we report the structure solutions and refinements in some detail. TMA.H20.2pA was obtained by recrystallization of 25 ml of an aqueous solution containing a total of 4.3 mmol of TMA plus PA. When the TMA:PA ratio in these solutions was 3:1, the predominant product was orthorhombic crystals of TMA.~4PA, together with some straw-colored triclinic needles of TMA.H20.2pA; when the ratio was 1"2, the latter crystals predominated. The composition of these triclinic needles did not appear to vary with the composition of the parent solution, since identical diffraction photographs were obtained from different preparations.Unit-cell dimensions for both crystals were measured from back-reflection Weissenberg photographs about all three axes, with Cu Ka radiation. The density of TMA.]HzO was measured by suspension in tolueneC2H4Br 2 solution, and that of TMA.H20.~PA by suspension in a CCl4-toluene solution. Crystal data are collected in Table 1. Chemical analyses of both compounds were carried out by Galbraith Laboratories. Crystals of TMA.H20.~PA give a diffraction pattern consisting of two components: (1) the Bragg (sharp) reflections that characterize the unit cell described in Table 1 and (2) a series of diffuse reflections which we ascribe to the PA molecules being ar- Table 1 ranged without long-range order but with a considerable degree of short-range order (Fig...

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Section: Molecular Dimensionsmentioning

confidence: 60%

The crystal structures of trimesic acid, its hydrates and complexes. II. Trimesic acid monohydrate–2/9 picric acid and trimesic acid 5/6 hydrate

Herbstein¹,

Marsh²

1977

Acta Crystallogr Sect B

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“…The N(l)-C (2) and N(2)-C(5) distances are typical of a C-N double bond [16,20]. The N(2)-C(lO) distance of 1.42 A is not unusual for a N-Ph single bond, and may be compared with C-N distances reported for various anilines [ 18,191. The o-xylyl fragment of the molecule also contains no anomalies.…”

Section: Structure Of Mtqd In the Solid Statementioning

confidence: 99%

X-ray structure and dynamic behaviour in solution of N-methylthio-N'-2,6-dimethylphenyl).2,6-dimethyl-1,4-quinonediimine formed by the alcoholysis of [Me2 Al{2,6-Me2C6H3NS(Me)NC6H3Me2-2,6}]2

Klerks

Koten

Vrieze

et al. 1981

Journal of Organometallic Chemistry

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Reaction of [Me2A1{RNS(Me)NRj], (R = 2,6-Me&H,) with t-BuOH affords N-methylthio-N'-(2,6-dimethylphenyl)-2,6-dimethyl-l,4-quinonediirnine in 67% yield. The X-ray structure of this compound shows that two confo~ational isomers are present in the solid. Temperature dependent 13C and 'H NMR measurements show that in solution these conformers exchange at a rate which is fast on the NMR time scale at +6O"C and slow at -60°C. From the coalescence point of two of the 13C resonances, the free energy of activation is estimated to be 13.7 + 1.0 kcallmol at 10°C. Possible processes for the exchange are discussed, and also a reaction scheme for the formation of the title compound is discussed.

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“…The structure of p-nitroaniline has been determined by Trueblood, Goldish & Donohue (1961) and later redetermined by Colapietro, Domenicano, Marciante & Portalone (1982). That of N,N-dimethyl-p-nitroaniline has also been reported (Mak & Trotter, 1965) (Johnson, 1976) of the molecular structure together with the atomic numbering system.…”

Section: Bond Distances (A) and Bond Angles (°)For Non-h Atoms Withmentioning

confidence: 99%

Structure of N-(p-nitrophenyl)ethylenediamine

Kaida¹,

Wakita²,

Shimizu³

et al. 1989

Acta Crystallogr C

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etry in the present study is more precise, with bond- Cryst. Struct. Commun. 10,[789][790][791][792].International Tables for X-ray Crystallography (1974 Experimental. The title compound (1) was prepared by a previously reported method (Linsker & Evans, 1945). Crystals were grown as brown plates from boiling water. A crystal with approximate dimensions 0.15×0.50×0.55mm was mounted on a * To whom correspondence should be addressed. (20) = (2.5 + 0"70 tan0) °. Background intensities were measured for 5 s at both ends of a scan. Four standard reflections (002, 044, 040, 500) were remeasured after every 60 reflections; no significant loss of intensity was observed throughout data collection. 1610 independent reflections (Rant=0.015) were collected with 20 up to 50.5 ° [(sin0)/a= 0.600 A -~] and index range of h = -11 to 12, k = 0 to 10, l---12 to 0. Corrections for Lorentz and polarization effects were applied to the intensity data; no absorption or extinction corrections were carried out.

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A three-dimensional refinement of the crystal structure of 4-nitroaniline

Cited by 200 publications

References 2 publications

The crystal structures of trimesic acid, its hydrates and complexes. II. Trimesic acid monohydrate–2/9 picric acid and trimesic acid 5/6 hydrate

The crystal structures of trimesic acid, its hydrates and complexes. II. Trimesic acid monohydrate–2/9 picric acid and trimesic acid 5/6 hydrate

X-ray structure and dynamic behaviour in solution of N-methylthio-N'-2,6-dimethylphenyl).2,6-dimethyl-1,4-quinonediimine formed by the alcoholysis of [Me2 Al{2,6-Me2C6H3NS(Me)NC6H3Me2-2,6}]2

Structure of N-(p-nitrophenyl)ethylenediamine

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