Abstract: From X-ray diffraction data, the crystal lattice of 1,2,3,4-tetrafluoronaphthalene 1 is composed of infinite pi-stacks revealing pi-pi interactions of the arene-arene, arene-polyfluoroarene and polyfluoroarene-polyfluoroarene types. On replacement of the C2-F fragment of 1 by a N atom (i.e. in going from 1 to 1,3,4-trifluoroisoquinoline 2) the enlarged offset of neighboring molecules within the stacks excludes their pi-pi interactions, and only the F-...pi interaction of fluorine atom of the C1-F bond of one molecule with hydrocarbon ring of another is observed. Networks of shortened C-(FH)-H-...-C (1 and 2) and (NH)-H-...-C (2) contacts also contribute to supramolecular tectonics of the crystals. Quantum chemical calculations at the PBE/cc-pVTZ level of theory on dimers of 1 and 2 result in geometries somewhat different from those observed in the solid state. (c) 2005 Elsevier B.V. All rights reserved.

Cite: Bagryanskaya I. , Gatilova Y. , Maksimov A. , Platonov V. , Zibarev A.
Supramolecular synthons in crystals of partially fluorinated fused aromatics: 1,2,3,4-Tetrafluoronaphthalene and its aza-analogue 1,3,4-trifluoroisoquinoline
Journal of Fluorine Chemistry. 2005. V.126. N9-10. P.1281-1287. DOI: 10.1016/j.jfluchem.2005.06.011 WOS Scopus РИНЦ OpenAlex

Dates:

Published print:

Oct 1, 2005

Identifiers:

Web of science:	WOS:000232818200003
Scopus:	2-s2.0-26444443067
Elibrary:	13481655
OpenAlex:	W2078747429

Citing:

DB	Citing
Web of science	33
Scopus	37
OpenAlex	36

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