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Pointers toward the Occurrence of $C-F^{...}F-C$ Interaction: Experimental Charge Density Analysis of 1-(4-Fluorophenyl)-3,6,6-trimethyl-2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one and 1-(4-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4- tetrahydroisoquinoline

Chopra, Deepak and Cameron, TS and Ferrara, Joseph D and Guru Row, Tayur N (2006) Pointers toward the Occurrence of $C-F^{...}F-C$ Interaction: Experimental Charge Density Analysis of 1-(4-Fluorophenyl)-3,6,6-trimethyl-2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one and 1-(4-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4- tetrahydroisoquinoline. In: The Journal of Physical Chemistry A, 110 (35). pp. 10465-10477.

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Abstract

A charge density study of crystalline 1-(4-fluorophenyl)-3,6,6-trimethyl-2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one (A) and 1-(4-fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (B) has been carried out using high-resolution X-ray diffraction data collected at 113(2) K. Weak intermolecular interactions of the type $C-H^.^.^.O$, $C-H^.^.^.\pi$, and $\pi^.^.^.\pi$ hold the molecules together in the crystal lattice along with interactions of the type $C-H^.^.^.F$ and unusual $C-F^.^.^.F-C$ examined via charge density analysis. The topological features are evaluated in terms of Bader’s theory of atoms in molecules through the first four criteria of Koch and Popelier. The $C-F^.^.^.F-C$ contact is observed to be across the center of symmetry in B and not in A, and further, this interaction appears to possess a certain correlation with the electron density properties at the critical point which suggests that such an interaction fits into the hierarchy of weak interactions.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 24 Oct 2006
Last Modified: 19 Sep 2010 04:32
URI: http://eprints.iisc.ernet.in/id/eprint/8756

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