Abstract: 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.

Cite: 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

Dates:

Published print:

Jun 1, 2006

Identifiers:

Web of science	WOS:000238164100011
Scopus	2-s2.0-33646532267
Elibrary	13513347
OpenAlex	W2060576084

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