Experimental and computational structural study of two hindered aminoanthraquinones in crystals and solutions
The crystal and molecular structures of 2-methyl-1-methylamino-anthraquinone (I) and 1-methylphenylamino-anthraquinone (II) were studied by the X-ray single-crystal diffraction and the visible spectra of crystalline specimens and their solutions were recorded. The molecule I is closely planar, where...
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| Published in | Zeitschrift für Kristallographie. Crystalline materials Vol. 215; no. 9; pp. 542 - 546 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
De Gruyter Oldenbourg
01.09.2000
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| Online Access | Get full text |
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| Abstract | The crystal and molecular structures of 2-methyl-1-methylamino-anthraquinone (I) and 1-methylphenylamino-anthraquinone (II) were studied by the X-ray single-crystal 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 π-delocalisation throughout the whole molecule enhances in the solid state. |
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| AbstractList | The crystal and molecular structures of 2-methyl-1-methylamino-anthraquinone (I) and 1-methylphenylamino-anthraquinone (II) were studied by the X-ray single-crystal 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 π-delocalisation throughout the whole molecule enhances in the solid state. |
| Author | Popov, S.I. Paseshnichenko, K.A. Yatsenko, A.V. |
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| Cites_doi | 10.1016/S0143-7208(00)00021-8 10.1246/nikkashi1898.64.6_1061 10.1016/S0166-1280(99)00170-0 10.1524/zkri.1998.213.9.466 10.1016/S0166-1280(96)04872-5 10.1039/p29930000799 10.1103/PhysRevA.38.3098 |
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| References_xml | – volume: 281 start-page: 151 year: 1997 ident: p_13 publication-title: Phys. Lett. contributor: fullname: Laikov D. N. – volume: 72 start-page: 223 year: 1987 ident: p_21 publication-title: Acta contributor: fullname: Bliznyuk A. A. – volume: 42 start-page: 2724 year: 1968 ident: p_28 publication-title: Zh. Fiz. Khim. contributor: fullname: Shcheglova N. A. – volume: 28 start-page: 1979 year: 1958 ident: p_9 publication-title: Zh. Obshch. Khim. contributor: fullname: Dokunikhin N. S. – volume: 55 start-page: 2858 year: 1981 ident: p_30 publication-title: Zh. Fiz. Khim. contributor: fullname: Rodionova G. N. – volume: 38 start-page: 1884 year: 1968 ident: p_29 publication-title: Zh. Obshch. Khim. contributor: fullname: Fokin E. P. – volume: 19 start-page: 153 year: 1983 ident: p_4 publication-title: Zh. Org. Khim. contributor: fullname: Kazankov M. V. – volume: 12 start-page: 2589 year: 1976 ident: p_2 publication-title: Zh. Org. Khim. contributor: fullname: Gorelik M. V. – ident: p_25 doi: 10.1016/S0143-7208(00)00021-8 – volume: 64 start-page: 1061 year: 1961 ident: p_27 publication-title: Kogyo Kagaku Zasshi doi: 10.1246/nikkashi1898.64.6_1061 contributor: fullname: Bansho Y. – ident: p_18 doi: 10.1016/S0166-1280(99)00170-0 – volume: 107 start-page: 3902 year: 1985 ident: p_16 publication-title: Soc. contributor: fullname: Dewar M. J. S. – volume: 213 start-page: 466 year: 1998 ident: p_5 publication-title: Z. Kristallogr. doi: 10.1524/zkri.1998.213.9.466 contributor: fullname: Yatsenko A. V. – volume: 32 start-page: 623 year: 1980 ident: p_24 publication-title: Zh. Prikl. Spektrosk. contributor: fullname: Rodionova G. N. – volume: 75 start-page: 3230 year: 1953 ident: p_26 publication-title: Soc. contributor: fullname: Bergmann E. D. – volume: 393 start-page: 31 year: 1997 ident: p_19 publication-title: J. Mol. Struct.: THEO HEM doi: 10.1016/S0166-1280(96)04872-5 contributor: fullname: AÂngyaÂn J. G – ident: p_23 doi: 10.1039/p29930000799 – volume: 2 start-page: 1357 year: 1983 ident: p_7 publication-title: Soc. Perkin Trans. contributor: fullname: Mathias A. – volume: 38 start-page: 3098 year: 1988 ident: p_14 publication-title: Phys. Rev. doi: 10.1103/PhysRevA.38.3098 contributor: fullname: Becke A. D. |
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| Title | Experimental and computational structural study of two hindered aminoanthraquinones in crystals and solutions |
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