OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS
Crystal and molecular structure of Michler’s ketone as a pure phase
Ibukun Oluwaseun Shotonwa (1) , Rene Theodoor Boere (2,*)
(1) Department of Chemistry, Lagos State University, Ojo, Lagos, 102101, Nigeria
(2) Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive West, Lethbridge, Alberta, T1K3M4, Canada
(*) Corresponding Author
Received: 15 Aug 2022 | Revised: 21 Sep 2022 | Accepted: 22 Sep 2022 | Published: 31 Dec 2022 | Issue Date: December 2022
The pure phase crystals of Michler’s ketone, [4-(CH3)2NC6H4]2CO, are reported herein as monoclinic in the space group P21/c with Z’ = 2 by single-crystal X-ray diffraction. The data collection of the title compound proved quite difficult, which could explain why the structure has not been reported previously. The crystallographically independent molecules in the asymmetric unit differ by dihedral angles of 24.60/30.34° and 25.25/27.20° between the essentially planar 4-dimethylaminophenyl (DMAP) rings and the central C2C=O plane of the ketone and dihedral angles of 52.14 and 47.41°, respectively, between the DMAP planes. A DMAP ring of each molecule overlaps in the lattice with a methyl ring that overlays the ring centroid of the opposite number (CMe-Cg distances of 3.452 and 3.505 Å), describing sets of trifurcated CAr-acceptor hydrogen bond interactions (HBIs). The trifurcated HBIs possess H∙∙∙CAr distances of 2.90, 2.75, and 2.86 Å; CMe∙∙∙Car distances of 3.554(5), 3.798(5) and 3.881(5) Å; and ÐCMe-H∙∙∙CAr of 115.0, 121.3 and 167.7°, respectively. Stabilization of the asymmetric unit in the title compound is further achieved by supramolecular synthons such as CMe-H∙∙∙CAr (2.831 Å), CAr-H∙∙∙O (2.561 Å) and CAr-H∙∙∙H-CAr (2.290 Å) and coulombic CMe-Ocontact (3.209 Å). The structures of the two independent molecules in the asymmetric unit of the title compound were compared with the same molecule as found in the following co-crystals, adducts or salts: a halogen-bonded adduct with 1,4-diiodotetrafluorobenzene; a hydrogen-bonded adduct with a fluorinated phenol; a coordination complex between the ketone and a trimeric mercury acceptor; and two salts from protonation or methylation at one of the amino nitrogen atoms.
Links for Article
| | | | | | |
| | | | | | |
| | | |
Article MetricsThis Abstract was viewed 77 times | PDF Article downloaded 20 times
Lagos State University, Ojo, Lagos, 102101, Nigeria and University of Lethbridge, Lethbridge, Alberta, T1K3M4, Canada.
. Michler, W. Synthese aromatischer Ketone mittelst Chlorkohlenoxyd. Ber. Dtsch. Chem. Ges. 1876, 9, 716-718.
. Sabnis, R. W. Handbook of biological dyes and stains: Synthesis and industrial applications; Wiley-Blackwell: Hoboken, NJ, 2010.
. Kan, R. O. Organic Photochemistry; McGraw-Hill: New York, NY, 1967.
. Claibourne, D. S. Quadricyclane. Organic Synth. 1971, 51, 133.
. Groom, C. R.; Bruno, I. J.; Lightfoot, M. P.; Ward, S. C. The Cambridge Structural Database. Acta Crystallogr. B Struct. Sci. Cryst. Eng. Mater. 2016, 72, 171-179.
. Syssa-Magalé, J.-L.; Boubekeur, K.; Schöllhorn, B. First molecular self-assembly of 1,4-diiodo-tetrafluoro-benzene and a ketone via (O⋯I) non-covalent halogen bonds. J. Mol. Struct. 2005, 737, 103-107.
. Gramstad, T.; Husebye, S.; Maartmann-Moe, K.; Sæbø, J.; Fischer, G. W. Complex formation involving 4,4'-bis(dimethylamino)benzophenone (michler's ketone). The crystal structures of the 1:1 hydrogen-bonded complexes with trifluoromethanesulfonic acid and pentafluoro phenol. Acta Chem. Scand. 1987, 41b, 555-563.
. Fisher, S. P.; Reinheimer, E. W. Complexation of Michler's ketone by trimeric perfluoro-ortho-phenylenemercury: Synthesis, structure and spectroscopic properties of a new supramolecular adduct. J. Chem. Crystallogr. 2013, 43, 478-483.
. Moore, P. W.; Hooker, J. P.; Zavras, A.; Khairallah, G. N.; Krenske, E. H.; Bernhardt, P. V.; Quach, G.; Moore, E. G.; O'Hair, R. A. J.; Williams, C. M. Hydroxyl radicals via collision-induced dissociation of trimethyl ammonium benzyl alcohols. Aust. J. Chem. 2017, 70, 397-406.
. King, J. B.; Tsunoda, M.; Gabbaï, F. P. Complexation of aldehydes and ketones by trimeric perfluoro-ortho-phenylene mercury, a tridentate Lewis acid. Organometallics 2002, 21, 4201-4205.
. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339-341.
. Sheldrick, G. M. SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr. A Found. Adv. 2015, 71, 3-8.
. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.
. Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. Mercury 4.0: from visualization to analysis, design and prediction. J. Appl. Crystallogr. 2020, 53, 226-235.
. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Guy Orpen, A.; Taylor, R. Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J Chem Soc Perkin Trans 2 1987, S1-S19.
. Deng, J.-H.; Luo, J.; Mao, Y.-L.; Lai, S.; Gong, Y.-N.; Zhong, D.-C.; Lu, T.-B. π-π stacking interactions: Non-negligible forces for stabilizing porous supramolecular frameworks. Sci. Adv. 2020, 6, eaax9976.
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.13.4.435-439.2327
| | | | | | | |
| | | | | | |
Save to Zotero Save to Mendeley
European Journal of Chemistry 2022, 13(4), 435-439 | doi: https://doi.org/10.5155/eurjchem.13.4.435-439.2327 | Get rights and content
- There are currently no refbacks.
Copyright (c) 2022 Authors
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.