Molecular structure of 9,10-bis[bis(4-tert-butylphenyl)methylene)-9,10-dihydroanthracene: A butterfly-shaped Thiele's hydrocarbon derivative |
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Authors: | Firyon Ko Kazunori Hirabayashi Toshio Shimizu Ken-ichi Sugiura |
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Affiliation: | Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachi-Oji, Tokyo 192-0397, Japan |
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Abstract: | The molecular structure of 9,10-bis[bis(4-tert-butylphenyl)methylene)-9,10-dihydroanthracene, an anthraquinodimethane derivative having four aryl groups on exocyclic methylene positions, was experimentally and theoretically characterized. Single-crystal diffraction study revealed that the title molecule takes a butterfly shape, i.e., two exocyclic carbons rise from the molecular plane, defined by four carbons of central quinoidal ring, by 1.257(3) Å (average). The dihedral angle of the butterfly wing, i.e., the angle between the two annulated benzenes is 137.71(5)°. Characteristic bond alternation was observed for the central quinoidal moiety and the exocyclic double bond. Theoretical study indicated that this butterfly shape is the stable structure. The two optimized structures nearly reproduced the experimentally observed molecular structures, bond distances, and angles. |
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Keywords: | Thiele's hydrocarbon Single-crystal diffraction study Butterfly structure Theoretical study |
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