Peculiarities of Supramolecular Organization of Cyclic Ketones with Vinylacetylene Fragments Научная публикация
Журнал |
Acta Crystallographica Section C
, E-ISSN: 2053-2296 |
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Вых. Данные | Год: 2018, Том: 74, Номер: 12, Страницы: 1674-1683 Страниц : 10 DOI: 10.1107/s2053229618015838 | ||||||||
Ключевые слова | supramolecular organization; crystal structure; cyclic ketones; cyclohexanone; full interaction map; vinylacetylene fragments | ||||||||
Авторы |
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Организации |
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Информация о финансировании (2)
1 | Российский научный фонд | 16-13-10404 |
2 | Министерство образования и науки Российской Федерации | 14.619.21.0007 (RFMEFI61917X0007)(АААА-А18-118011190114-0) |
Реферат:
1,5-Diaryl(heteroaryl)pentenynones show a tendency to crystallize in acentric space groups due to their inclination to form C—H...O hydrogen-bonded chains instead of dimers and thus exhibit nonlinear optical properties. A series of symmetrical α,α′-bis(3-arylprop-2-yn-1-ylidene)cycloalkanones and unsymmetrical α-(furan-2-ylmethylene)-α′-(3-arylprop-2-yn-1-ylidene)cyclohexanones closely related to pentenynones was synthesized, namely 2,5-bis(3-phenylprop-2-yn-1-ylidene)cyclopentanone, C23H16O, 2,5-bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclopentanone, C23H14Br2O, 2,6-bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone, C24H18O, 2,6-bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclohexanone, C24H16Br2O, 4-tert-butyl-2,6-bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone, C28H25O, 4-tert-butyl-2,6-bis[3-(4-methylphenyl)prop-2-yn-1-ylidene]cyclohexanone, C30H30O, 2-(furan-2-ylmethylene)-6-(3-phenylprop-2-yn-1-ylidene)cyclohexanone, C20H16O2, and 6-(3-butylprop-2-yn-1-ylidene)-2-(furan-2-ylmethylene)cyclohexanone, C10H20O2, and investigated by means of X-ray diffraction to understand peculiarities of their supramolecular organization. Four of the eight novel compounds crystallize in acentric space groups. Three of these four compounds contain substituents at the para position of the phenyl ring, which affect the charge density on the H(CPh) atoms and thus stabilize CPh—H...O interactions. The fourth compound realizes the C—H...O hydrogen bonding via H atoms of the furyl ring. The applicability and shortcomings of the Full Interaction Map tool to predict the likelihood of C—H...O and C—H...Br hydrogen-bonded motifs, and the effect of substituents on the phenyl ring on the supramolecular architecture are discussed.
Библиографическая ссылка:
Voronova E.D.
, Golovanov A.A.
, Odin I.S.
, Anisimov M.A.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Vologzhanina A.V.
Peculiarities of Supramolecular Organization of Cyclic Ketones with Vinylacetylene Fragments
Acta Crystallographica Section C. 2018. V.74. N12. P.1674-1683. DOI: 10.1107/s2053229618015838 WOS Scopus РИНЦ
Peculiarities of Supramolecular Organization of Cyclic Ketones with Vinylacetylene Fragments
Acta Crystallographica Section C. 2018. V.74. N12. P.1674-1683. DOI: 10.1107/s2053229618015838 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: | 13 сент. 2018 г. |
Принята к публикации: | 7 нояб. 2018 г. |
Опубликована online: | 21 нояб. 2018 г. |
Опубликована в печати: | 1 дек. 2018 г. |
Идентификаторы БД:
Web of science | WOS:000452192900015 |
Scopus | 2-s2.0-85057080527 |
РИНЦ | 38618478 |
Chemical Abstracts | 2018:2404212 |
OpenAlex | W2901703571 |