Next Article in Journal
Hot Spots for Protein Partnerships at the Surface of Cholinesterases and Related α/β Hydrolase Fold Proteins or Domains—A Structural Perspective
Next Article in Special Issue
On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
Previous Article in Journal
Comparative Transcriptome Analysis of Genes Involved in Anthocyanin Biosynthesis in Red and Green Walnut (Juglans regia L.)
Previous Article in Special Issue
Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines
Article Menu
Issue 1 (January) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(1), 22; https://doi.org/10.3390/molecules23010022

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

1
Núcleo de Química de Heterociclos (NUQUIMHE), Department of Chemistry, Federal University of Santa Maria (UFSM), 97105-900 Santa Maria, Brazil
2
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)
View Full-Text   |   Download PDF [5516 KB, uploaded 25 December 2017]   |  

Abstract

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
Figures

Graphical abstract

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).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top