Structural considerations on acridine/acridinium derivatives : synthesis, crystal structure, Hirshfeld surface analysis and computational studies

Michał Wera , Piotr Storoniak , Illia Serdiuk , Beata Zadykowicz

Abstract

This article describes a detailed study of the molecular packing and intermolecular interactions in crystals of four derivatives of acridine, i.e. 9-methyl-, 9-ethyl, 9-bromomethyl- and 9-piperidineacridine (1, 2, 3 and 4, respectively) and three 10-methylacridinium salts containing the trifluoromethanesulphonate anion and 9-vinyl-, 9-bromomethyl, and 9-phenyl-10-methylacridinium cations (5, 6 and 7, respectively). The crystal structures of all of the compounds are stabilized by long-range electrostatic interactions, as well as by a network of short-range C–H⋅⋅⋅O (in hydrates and salts 3 and 5–7, respectively), C–H⋅⋅⋅π, π–π, C–F⋅⋅⋅π and S–O⋅⋅⋅π (in salts 5–7) interactions. Hirshfeld surface analysis shows that various intermolecular contacts play an important role in the crystal packing, graphically exhibiting the differences in spatial arrangements of the acridine/acridinium derivatives under scrutiny here. Additionally, computational methods have been used to compare the intermolecular interactions in the crystal structures of the investigated compounds. Computations have confirmed the great contribution of dispersive interactions for crystal lattice stability in the case of 9-substituted acridine and electrostatic interactions for the crystal lattice stability in the case of 9-substituted 10-methylacridinium trifluoromethanesulphonates. The value of crystal lattice energy and the electrostatic contribution in the crystal lattice energy of monohydrated acridine derivatives have confirmed that these compounds have behave as acridinium derivatives.
Author Michał Wera PK
Michał Wera,,
- Pracownia Krystalochemii
, Piotr Storoniak PSB
Piotr Storoniak,,
- Laboratory of Biological Sensitizers
, Illia Serdiuk PK
Illia Serdiuk,,
- Pracownia Krystalochemii
, Beata Zadykowicz PBL
Beata Zadykowicz,,
- Laboratory of Luminescence Research
Journal seriesJournal of Molecular Structure, ISSN 0022-2860
Issue year2016
Vol1105
Pages41-53
Publication size in sheets0.6
Keywords in Englishacridine and 10-methylacridinium derivatives, crystal structure, intra- and intermolecular interactions, Hirshfeld surface analysis
DOIDOI:10.1016/j.molstruc.2015.10.041
URL http://dx.doi.org/10.1016/j.molstruc.2015.10.041
Languageen angielski
Score (nominal)20
ScoreMinisterial score = 20.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 1.753 (2) - 2016=1.561 (5)
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