Structure of 1-morpholinoanthraquinone at 110 K

Kaufmann, Markus; Berger, Daniela; Härter, Ralph; Hirschi, Daniel; Bürgi, Hans‐Beat; Raselli, Andrea; Röhr, Caroline

doi:10.1107/s0108270191014336

Cited by 1 publication

(2 citation statements)

References 4 publications

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“…Principal experimental and calculated geometric parameters for structure II are given in Table 4. The geometry of the amino group in this molecule and in 1-morpholinoanthraquinone [6] are quite different: in II the environment of the N atom is essentially planar, and the twist angle about the C1± ±N bond is considerably larger. The C1± ±N bond in II is the longest one among all known structures containing 1-aminoanthraquinone moiety, and the alternation of C± ±C bonds (D(C± ±C)) in the N-substituted terminal ring is essentially absent here.…”

Section: Resultsmentioning

confidence: 98%

“…In the structure of 1-morpholinoanthraquinone the environment of the nitrogen atom is tetrahedrised, and the morpholine subunit is twisted by 21 about the C1± ±N bond [6]. The NMR 13 C spectrum of the solid 1-dimethylaminoanthraquinone indicated that two methyl groups are inequivalent, although in solutions an averaged chemical shift is observed because of rotation about the C1± ±N bond [7].…”

Section: Introductionmentioning

confidence: 96%

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Experimental and computational structural study of two hindered aminoanthraquinones in crystals and solutions

Yatsenko¹,

Paseshnichenko²,

Popov³

2000

Zeitschrift Für Kristallographie - Crystalline Materials

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The crystal and molecular structures of 2-methyl-1-methylamino-anthraquinone (I) and 1-methylphenylamino-anthraquinone (II) were studied by the X-ray singlecrystal diffraction and the visible spectra of crystalline specimens and their solutions were recorded. The molecule I is closely planar, whereas in the molecule II the amino group is 58 rotated out of the plane of the anthraquinone skeleton. In both structures the molecules pack in stacks. The comparison of experimental and calculated (on the DFT and AM1 levels) molecular structures, together with the comparison of experimental and INDO/S-calculated electronic spectra, give the evidence that molecular conformations (especially for II) change upon transfer from the solid state to solutions, and the p-delocalisation throughout the whole molecule enhances in the solid state.

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 96%