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Molecules 2018, 23(1), 22; doi:10.3390/molecules23010022

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes

Núcleo de Química de Heterociclos (NUQUIMHE), Department of Chemistry, Federal University of Santa Maria (UFSM), 97105-900 Santa Maria, Brazil
Núcleo de Investigação de Triazenos e Complexos (NITRICO), Department of Chemistry, Federal University of Santa Maria (UFSM), 97105-900 Santa Maria, Brazil
Author to whom correspondence should be addressed.
Received: 1 December 2017 / Revised: 18 December 2017 / Accepted: 19 December 2017 / Published: 22 December 2017
(This article belongs to the Special Issue Pyrazole Derivatives)
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Understanding the supramolecular environment of crystal structures is necessary to facilitate designing molecules with desirable properties. A series of 12 novel 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzenes was used to assess the existence of planar stacking columns in supramolecular structures of pyrazoles. This class of molecules with different substituents may assist in understanding how small structural changes affect the supramolecular environment. The obtained compounds did not present the formation of planar stacking interactions between benzenes in solid or liquid states. This supposition was indicated by single crystal diffraction, Density Functional Theory (DFT) and quantum theory of atoms in molecules (QTAIM) calculations, and concentration-dependent liquid-state 1H nuclear magnetic resonance (NMR). NMR showed that chemical shifts of benzene and pyrazole hydrogens confirm that planar stacking interactions are not formed in solution. The crystalline structures presented different molecular conformations. The molecular structures of 5 and 9b are in a twisted conformation, while compound 7 showed a conformation analogous to a calyx form. View Full-Text
Keywords: pyrazoles; crystal structure; QTAIM; NMR; X-ray; supramolecular chemistry; crystal engineering pyrazoles; crystal structure; QTAIM; NMR; X-ray; supramolecular chemistry; crystal engineering

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Martins, M.A.P.; Meyer, A.R.; Salbego, P.R.S.; dos Santos, D.M.; de Moraes, G.A.; Bonacorso, H.G.; Zanatta, N.; Frizzo, C.P.; Hörner, M. Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes. Molecules 2018, 23, 22.

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