Charge assisted assembly of zwitterionic pyridone hydrates
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2021
Authors
Mašulović, AleksandraLađarević, Jelena
Radovanović, Lidija
Vitnik, Zeljko J.
Vitnik, Vesna D.
Rogan, Jelena
Mijin, Dušan
Article (Published version)
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Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1.2H(2)O) or four (2.4H(2)O) water molecules. The zwitteri-onic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL latti...ce energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole-dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1.H2O and 2.4H(2)O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.
Keywords:
Computational chemistry / Hydrates / Pyridone / Stacking interactions / ZwitterionsSource:
Journal of Molecular Structure, 2021, 1237Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200135)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200287)
DOI: 10.1016/j.molstruc.2021.130419
ISSN: 0022-2860
WoS: 000646451900001
Scopus: 2-s2.0-85104288082
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Inovacioni centarTY - JOUR AU - Mašulović, Aleksandra AU - Lađarević, Jelena AU - Radovanović, Lidija AU - Vitnik, Zeljko J. AU - Vitnik, Vesna D. AU - Rogan, Jelena AU - Mijin, Dušan PY - 2021 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4911 AB - Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1.2H(2)O) or four (2.4H(2)O) water molecules. The zwitteri-onic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole-dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1.H2O and 2.4H(2)O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done. T2 - Journal of Molecular Structure T1 - Charge assisted assembly of zwitterionic pyridone hydrates VL - 1237 DO - 10.1016/j.molstruc.2021.130419 ER -
@article{ author = "Mašulović, Aleksandra and Lađarević, Jelena and Radovanović, Lidija and Vitnik, Zeljko J. and Vitnik, Vesna D. and Rogan, Jelena and Mijin, Dušan", year = "2021", abstract = "Two pyridone derivatives, bearing the pyridinium moiety (1), or dimethylpyridinium moiety (2), have been synthesized and their crystal structures have been determined. The compounds crystalize in hydrated zwitterionic forms with either two (1.2H(2)O) or four (2.4H(2)O) water molecules. The zwitteri-onic networks contain different types of water clusters, generated into channels, incorporating them into the network by sandwiching. The type of channel depends on the crystal lattice and the nature of non-covalent interactions established between zwitterions as well as the number of water molecules incorporated into the architecture. 1 affords tubes filled in with water channels formed by water tetramers, contrary to 2, which affords a layered network altering the zwitterionic layer and the layer formed by water tetramers and hexamers. A detailed study of intermolecular interactions of both crystal structures and a quantification of interaction energies has been performed using PIXEL lattice energy calculations, giving an insight to a quantitative evaluation of interactions through Coulombic, disperse, repulsion and polarization energies. The strongest pairwise, in both structures, is found to be a dipole-dipole interaction between oppositely charged heterocyclic rings. The differences in the crystal packings of these hydrates have been elucidated by the fingerplot analysis. The comparative studies between experimental and calculated (DFT) data of molecules 1.H2O and 2.4H(2)O for systems of different complexity are performed. Furthermore, correlations of experimental and calculated bond lengths and the simulation of compound solvation with the CPCM model are done.", journal = "Journal of Molecular Structure", title = "Charge assisted assembly of zwitterionic pyridone hydrates", volume = "1237", doi = "10.1016/j.molstruc.2021.130419" }
Mašulović, A., Lađarević, J., Radovanović, L., Vitnik, Z. J., Vitnik, V. D., Rogan, J.,& Mijin, D.. (2021). Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure, 1237. https://doi.org/10.1016/j.molstruc.2021.130419
Mašulović A, Lađarević J, Radovanović L, Vitnik ZJ, Vitnik VD, Rogan J, Mijin D. Charge assisted assembly of zwitterionic pyridone hydrates. in Journal of Molecular Structure. 2021;1237. doi:10.1016/j.molstruc.2021.130419 .
Mašulović, Aleksandra, Lađarević, Jelena, Radovanović, Lidija, Vitnik, Zeljko J., Vitnik, Vesna D., Rogan, Jelena, Mijin, Dušan, "Charge assisted assembly of zwitterionic pyridone hydrates" in Journal of Molecular Structure, 1237 (2021), https://doi.org/10.1016/j.molstruc.2021.130419 . .