18970-55-3Relevant academic research and scientific papers
The synthesis and crystal structures of halogenated tolans p-X-C 6H4-C≡C-C6F5 and p-X-C 6F4-C≡C-C6H5 (X = F, Cl, Br, I)
Collings, Jonathan C.,Burke, Jacquelyn M.,Smith, Philip S.,Batsanov, Andrei S.,Howard, Judith A.K.,Marder, Todd B.
, p. 3172 - 3178 (2004)
A series of halogenated, partially fluorinated tolans of general formula p-X-C6H4-C≡C-C6F5 [X = I (1), Br (2), Cl (3), F (4)] and p-X-C6F4-C≡C-C 6H5 [X = I (5), Br (6)] have been prepared via palladium-catalysed Sonogashira cross-coupling, or for X = Cl (7), by nucleophilic aromatic substitution reactions. The single-crystal X-ray structures of 1-3 and 5-6 have been determined. The structures reveal that the molecular packing is characterized by either arene-perfluoroarene interactions (3), or halogen - halogen interactions (isomorphous 1 and 2), or neither (isomorphous 5 and 6). The structure of 3 represents the first fully determined crystal structure of a compound that contains a halogen atom other than fluorine, in which arene -perfluoroarene interactions are present.
