The X-ray molecular structures of twenty-three N1-4-nitrophenyl, 2,4-dinitrophenyl and 2,4,6-trinitrophenyl-2-pyrazolines
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2023
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ACS Publications
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Torralba, M. Carmen, et al. «X-Ray Molecular Structures of 23 N1-4-Nitrophenyl, 2,4-Dinitrophenyl, and 2,4,6-Trinitrophenyl-2-Pyrazolines». Crystal Growth & Design, vol. 23, n.o 2, febrero de 2023, pp. 1145-61.
Abstract
Crystallographic study of three series of N1-aryl substituted-2-pyrazolines, the aryl group being 4-nitrophenyl (series1), 2,4-dinitrophenyl (series2), and 2,4,6-trinitrophenyl (series3). The structural features, bond distances and angles as well as torsions for each single compound will be described and comparatively discussed with data for related heterocycles found in the Cambridge Structural Database (2020.2.0). A deeper look at the data has been achieved to know the influence of the substituents on the molecular structures. In the crystals of compounds with stereogenic centers at positions 4 and 5, the presence of both enantiomers has been encountered in 12 cases out of 14 that include a literature result. Finally, molecular packings in all series have been analyzed reaching the conclusion that they follow several patterns depending on the existence or not, and the type of intermolecular interactions. A general pattern has been observed which implies a certain tendency of the molecules to arrange into chains, whose additional contacts could extend the dimensionality of the network.
Description
2-Pyrazolines have important properties that can be divided into two topics, physical and biological. The first set comprises their use as ligands in organometallic chemistry, as organic light-emitting diodes, fluorescent probes, and molecular dyes, as well as their optoelectronic features.
However it is in what concerns medicinal chemistry that pyrazolines show their most representative properties including anticancer; antimicrobial; antischistosomal; antitubercular; anti-inflammatory; CB1 receptor antagonists (antiobesity); antidiabetic; anti-Parkinson; inhibitor of urease; immunosuppressive; antidepressant; CNS uses; 18F labeled radiotracers; and chemical libraries.
1-Nitropheny-2-pyrazolines are promising in these fields being brightly colored but still remain very little explored. The 1-(2,4-dinitrophenyl) derivatives are much less frequent because the cyclization of the 2,4-dinitrophenylhydrazones of α,β-unsaturated carbonyl compounds was rarely successful. Finally, the 1-(2,4,6-trinitrophenyl) derivatives have only been prepared by our group.
In the present paper, we report the determination of the crystal structures of 23 2-pyrazolines N-substituted by 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6-trinitrophenyl groups which will be discussed together with the three structures determined in the literature. Structural features and molecular packings are comparatively discussed with data for related heterocycles found in the Cambridge Structural Database (2020.2.0)