18970-56-4Relevant academic research and scientific papers
Thermodynamics of halogen bonding in solution: Substituent, structural, and solvent effects
Sarwar, Mohammed G.,Dragisic, Bojan,Salsberg, Lee J.,Gouliaras, Christina,Taylor, Mark S.
supporting information; scheme or table, p. 1646 - 1653 (2010/04/04)
A detailed study of the thermodynamics of the halogen-bonding interaction in organic solution is presented. 19F NMR titrations are used to determine association constants for the interactions of a variety of Lewis bases with fluorinated iodoalkanes and iodoarenes. Linear free energy relationships for the halogen bond donor ability of substituted iodoperfluoroarenes XC 6F4I are described, demonstrating that both substituent constants (σ) and calculated molecular electrostatic potential surfaces are useful for constructing such relationships. An electrostatic model is, however, limited in its ability to provide correlation with a more comprehensive data set in which both halogen bond donor and acceptor abilities are varied: the ability of computationally derived binding energies to accurately model such data is elucidated. Solvent effects also reveal limitations of a purely electrostatic depiction of halogen bonding and point to important differences between halogen bonding and hydrogen bonding.
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 (2007/10/03)
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.
