Single crystal X-ray diffraction and PIXEL calculation of intermolecular pair energies, with partitioning into coulombic and dispersive factors, have been performed on the title crystals with the aim of testing the relative efficiency of molecular recognition synthons. X-Ray diffraction reveals that the crystals contain extended hydrogen-bonded layers, with various degrees of aromatic ring overlap between the layers. The calculation of molecular pair energies quantitatively reveals that the primary binding force in these crystals is hydrogen bonding, and that the arene-perfluoroarene stacking mode becomes less important, or almost optional. The various degrees of offset between overlapping aromatic rings found in the present crystals, also in comparison with some non-hydrogen bonding analogs, suggest a transition from perfect, highly stabilizing Ar H-Ar F overlap, to the less favourable, but still energetically stabilizing, Ar F-Ar F and Ar H-Ar H overlaps. The selectivity towards Ar H-Ar F stacking is not overwhelming.

Competition between hydrogen bonding and arene-perfluoroarene stacking : X-Ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide / F. Cozzi, S. Bacchi, G. Filippini, T. Pilati, A. Gavezzotti. - In: CRYSTENGCOMM. - ISSN 1466-8033. - 11:6(2009), pp. 1122-1127.

Competition between hydrogen bonding and arene-perfluoroarene stacking : X-Ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide

F. Cozzi
Primo
;
S. Bacchi
Secondo
;
A. Gavezzotti
Ultimo
2009

Abstract

Single crystal X-ray diffraction and PIXEL calculation of intermolecular pair energies, with partitioning into coulombic and dispersive factors, have been performed on the title crystals with the aim of testing the relative efficiency of molecular recognition synthons. X-Ray diffraction reveals that the crystals contain extended hydrogen-bonded layers, with various degrees of aromatic ring overlap between the layers. The calculation of molecular pair energies quantitatively reveals that the primary binding force in these crystals is hydrogen bonding, and that the arene-perfluoroarene stacking mode becomes less important, or almost optional. The various degrees of offset between overlapping aromatic rings found in the present crystals, also in comparison with some non-hydrogen bonding analogs, suggest a transition from perfect, highly stabilizing Ar H-Ar F overlap, to the less favourable, but still energetically stabilizing, Ar F-Ar F and Ar H-Ar H overlaps. The selectivity towards Ar H-Ar F stacking is not overwhelming.
Settore CHIM/02 - Chimica Fisica
Settore CHIM/06 - Chimica Organica
2009
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/67217
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 22
  • ???jsp.display-item.citation.isi??? 22
social impact