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Unexpectedly low affinity of aromatic disulfides for pi-stacking interactions of the arene-polyfluoroarene type Научная публикация

Журнал Journal of Fluorine Chemistry
ISSN: 0022-1139
Вых. Данные Год: 2006, Том: 127, Номер: 6, Страницы: 746-754 Страниц : 9 DOI: 10.1016/j.jfluchem.2006.02.007
Ключевые слова stacking interactions; supramolecular synthons; self-assembled monolayers; crystal engineering; x-ray structures
Авторы Bagryanskaya Irina Yu. , Gatilov Yuri V. , Lork Enno , Mews Ruediger , Zibarev Andrey V.
Организации
1 (Данные Web of science) Univ Bremen, Inst Inorgan & Phys Chem, D-28334 Bremen, Germany
2 (Данные Web of science) Russian Acad Sci, Inst Organ Chem, Novosibirsk 630090, Russia
3 (Данные Web of science) Novosibirsk State Univ, Dept Phys, Novosibirsk 630090, Russia

Реферат: 1,2,3,4,5-Pentafluorodiphenyl disulfide (1) was synthesized from C6F5SCl and C6H5SSiMe3 in quantitative yield. The homo-crystals of disulfide 1 and co-crystals of 1,1',2,2',3,3',4,4,5,5'-decafluorodiphenyl disulfide (2) with naphthalene (stoichiometry 1:2, complex 4) and diphenyl disulfide (3) with octafluoronaphthalene (stoichiometry 2: 1, complex 5) were prepared followed by XRD characterization. In the crystal lattice of 1, face-to-face and face-to-edge Ph-H/Ph-F orientations of neighboring rings were observed together with face-to-edge Ph-F/Ph-F orientations. For the face-to-face Ph-H/Ph-F orientation, the large offset of Ph-H and Ph-F groups excludes their pi-stacking interaction which is very non-typical of the field. The crystal lattice of 4 reveals standard pi-stacking interactions of the arene-polyfluoroarene type. While in the lattice of 4 each Ph-F ring interacts alternating with naphthalenes, in 5 two disulfides 3 are bridged by one octafluoronaphthalene with only one of the Ph-H rings of each disulfide interacting with the polyfluoroarene pi-system. The large offset of neighboring molecules excludes however their pi-stacking interactions in complex 5. An attempt to prepare 2/3 co-crystals failed. (c) 2006 Elsevier B.V. All rights reserved.
Библиографическая ссылка: Bagryanskaya I.Y. , Gatilov Y.V. , Lork E. , Mews R. , Zibarev A.V.
Unexpectedly low affinity of aromatic disulfides for pi-stacking interactions of the arene-polyfluoroarene type
Journal of Fluorine Chemistry. 2006. V.127. N6. P.746-754. DOI: 10.1016/j.jfluchem.2006.02.007 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 июн. 2006 г.
Идентификаторы БД:
Web of science: WOS:000238164100011
Scopus: 2-s2.0-33646532267
РИНЦ: 13513347
OpenAlex: W2060576084
Цитирование в БД:
БД Цитирований
Web of science 5
Scopus 5
OpenAlex 5
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