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Acta Crystallographica Section E: Crystallographic Communications, volume 78, issue 2, pages 169-172
Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine
Publication type: Journal Article
Publication date: 2022-01-14
Quartile SCImago
Q3
Quartile WOS
—
Impact factor: 0.6
ISSN: 20569890
PubMed ID:
35145745
General Chemistry
Condensed Matter Physics
General Materials Science
Abstract
The title compounds, 2-(4-methylphenyl)-1H-perimidine hemihydrate (1, C18H14N2·0.5H2O) and 1-methyl-2-(4-methylphenyl)-1H-perimidine (2, C19H16N2), were prepared and characterized by 1H NMR and single-crystal X-ray diffraction. The organic molecule of the hemihydrate lies on a twofold rotation axis while the water molecule lies on the intersection of three twofold rotation axes (point group symmetry 222). As a consequence, the hydrogen atoms that are part of the N—H group and the water molecule as well as the CH3 group of the p-tolyl ring are disordered over two positions. In compound 1, the perimidine and the 2-aryl rings are slightly twisted while its N-methylated derivative 2 has a more distorted conformation because of the steric repulsion between the N-methyl group and the 2-aryl ring. In the crystal structures, molecules of perimidine 2 are held together only by C—H...π contacts while the parent perimidine 1 does not exhibit this type of interaction. Its crystal packing is established by intermolecular N—H...O hydrogen bonds with the solvent water molecules and additionally stabilized by π–π stacking.
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Kalle P. et al. Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine // Acta Crystallographica Section E: Crystallographic Communications. 2022. Vol. 78. No. 2. pp. 169-172.
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Kalle P., Tatarin S. V., Kiseleva M. A., Zakharov A. Y., Smirnov D. E., Bezzubov S. I. Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine // Acta Crystallographica Section E: Crystallographic Communications. 2022. Vol. 78. No. 2. pp. 169-172.
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TY - JOUR
DO - 10.1107/S2056989022000287
UR - https://doi.org/10.1107%2FS2056989022000287
TI - Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine
T2 - Acta Crystallographica Section E: Crystallographic Communications
AU - Zakharov, Alexander Yu.
AU - Bezzubov, Stanislav I.
AU - Smirnov, Daniil E.
AU - Kalle, Paulina
AU - Tatarin, Sergei V.
AU - Kiseleva, Marina A.
PY - 2022
DA - 2022/01/14 00:00:00
PB - International Union of Crystallography (IUCr)
SP - 169-172
IS - 2
VL - 78
PMID - 35145745
SN - 2056-9890
ER -
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@article{2022_Kalle,
author = {Alexander Yu. Zakharov and Stanislav I. Bezzubov and Daniil E. Smirnov and Paulina Kalle and Sergei V. Tatarin and Marina A. Kiseleva},
title = {Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine},
journal = {Acta Crystallographica Section E: Crystallographic Communications},
year = {2022},
volume = {78},
publisher = {International Union of Crystallography (IUCr)},
month = {jan},
url = {https://doi.org/10.1107%2FS2056989022000287},
number = {2},
pages = {169--172},
doi = {10.1107/S2056989022000287}
}
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Kalle, Paulina, et al. “Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine.” Acta Crystallographica Section E: Crystallographic Communications, vol. 78, no. 2, Jan. 2022, pp. 169-172. https://doi.org/10.1107%2FS2056989022000287.