А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins
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2019
Konferencijski prilog (Objavljena verzija)
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Prikaz svih podataka o dokumentuApstrakt
A series of spirohydantoins derived from α-tetralone (Figure 1) was synthesized and the
compounds were characterized using the melting point measurements, FTIR, 1H and 13C
NMR spectroscopic methods. The molecular conformation, crystal packing properties
and intermolecular interactions of 1-(4-methoxybenzyl)-3’,4’-dihydro-2Hspiro[
imidazolidine-4,1’-naphtalene]-2,5-dione were analyzed by single crystal X-ray
diffraction and quantum chemical calculations. The crystal packing of this compound
(monoclinic, P21/c, a = 12.682(3), b = 6.4568(13), c = 20.826(4) Å, β = 98.61(3) °, R =
4.3%) contains centrosymmetric dimmers linked by N–H···O hydrogen bonds, which
are further connected via C–H···O, C–H···π and parallel interactions of the phenyl rings
at a large offset (PILO) to form infinite pseudo-layers. As a result, the pseudo-layers are
associated into highly ordered three-dimensional framework along the b-axis. By
combination of the crystal packing analysis and quantum chemical c...alculations, it was
concluded that the structural motif formed by N–H···O hydrogen bonds between
hydantoin rings is the most stable in the crystal structure. It was shown that the
introduction of an electron-donating substituent into the benzyl moiety leads to
strengthening of N–H···O hydrogen bonds, while an electron-accepting substituent has
the opposite effect. The introduction of substituents enhances the stacking, C–H···π and
PILO interactions, so it is expected that PILO interactions are the most represented in
the crystal structures, as shown by statistical analysis of crystal structures of benzene
molecules from Cambridge Structural Database.[1]
Figure 1. The chemical structure of the investigated compounds.
Ključne reči:
spirohydantoins / intermolecular interactions / crystallographic and theoretical studyIzvor:
Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019, 2019, 90-Izdavač:
- Belgrade : Serbian Chemical Society
Institucija/grupa
Inovacioni centarTY - CONF AU - Lazić, Anita M. AU - Gak, Kristina G. AU - Radovanović, Lidija D. AU - Đorđević, Ivana S. PY - 2019 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7406 AB - A series of spirohydantoins derived from α-tetralone (Figure 1) was synthesized and the compounds were characterized using the melting point measurements, FTIR, 1H and 13C NMR spectroscopic methods. The molecular conformation, crystal packing properties and intermolecular interactions of 1-(4-methoxybenzyl)-3’,4’-dihydro-2Hspiro[ imidazolidine-4,1’-naphtalene]-2,5-dione were analyzed by single crystal X-ray diffraction and quantum chemical calculations. The crystal packing of this compound (monoclinic, P21/c, a = 12.682(3), b = 6.4568(13), c = 20.826(4) Å, β = 98.61(3) °, R = 4.3%) contains centrosymmetric dimmers linked by N–H···O hydrogen bonds, which are further connected via C–H···O, C–H···π and parallel interactions of the phenyl rings at a large offset (PILO) to form infinite pseudo-layers. As a result, the pseudo-layers are associated into highly ordered three-dimensional framework along the b-axis. By combination of the crystal packing analysis and quantum chemical calculations, it was concluded that the structural motif formed by N–H···O hydrogen bonds between hydantoin rings is the most stable in the crystal structure. It was shown that the introduction of an electron-donating substituent into the benzyl moiety leads to strengthening of N–H···O hydrogen bonds, while an electron-accepting substituent has the opposite effect. The introduction of substituents enhances the stacking, C–H···π and PILO interactions, so it is expected that PILO interactions are the most represented in the crystal structures, as shown by statistical analysis of crystal structures of benzene molecules from Cambridge Structural Database.[1] Figure 1. The chemical structure of the investigated compounds. PB - Belgrade : Serbian Chemical Society C3 - Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019 T1 - А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins SP - 90 UR - https://hdl.handle.net/21.15107/rcub_technorep_7406 ER -
@conference{ author = "Lazić, Anita M. and Gak, Kristina G. and Radovanović, Lidija D. and Đorđević, Ivana S.", year = "2019", abstract = "A series of spirohydantoins derived from α-tetralone (Figure 1) was synthesized and the compounds were characterized using the melting point measurements, FTIR, 1H and 13C NMR spectroscopic methods. The molecular conformation, crystal packing properties and intermolecular interactions of 1-(4-methoxybenzyl)-3’,4’-dihydro-2Hspiro[ imidazolidine-4,1’-naphtalene]-2,5-dione were analyzed by single crystal X-ray diffraction and quantum chemical calculations. The crystal packing of this compound (monoclinic, P21/c, a = 12.682(3), b = 6.4568(13), c = 20.826(4) Å, β = 98.61(3) °, R = 4.3%) contains centrosymmetric dimmers linked by N–H···O hydrogen bonds, which are further connected via C–H···O, C–H···π and parallel interactions of the phenyl rings at a large offset (PILO) to form infinite pseudo-layers. As a result, the pseudo-layers are associated into highly ordered three-dimensional framework along the b-axis. By combination of the crystal packing analysis and quantum chemical calculations, it was concluded that the structural motif formed by N–H···O hydrogen bonds between hydantoin rings is the most stable in the crystal structure. It was shown that the introduction of an electron-donating substituent into the benzyl moiety leads to strengthening of N–H···O hydrogen bonds, while an electron-accepting substituent has the opposite effect. The introduction of substituents enhances the stacking, C–H···π and PILO interactions, so it is expected that PILO interactions are the most represented in the crystal structures, as shown by statistical analysis of crystal structures of benzene molecules from Cambridge Structural Database.[1] Figure 1. The chemical structure of the investigated compounds.", publisher = "Belgrade : Serbian Chemical Society", journal = "Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019", title = "А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins", pages = "90", url = "https://hdl.handle.net/21.15107/rcub_technorep_7406" }
Lazić, A. M., Gak, K. G., Radovanović, L. D.,& Đorđević, I. S.. (2019). А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins. in Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019 Belgrade : Serbian Chemical Society., 90. https://hdl.handle.net/21.15107/rcub_technorep_7406
Lazić AM, Gak KG, Radovanović LD, Đorđević IS. А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins. in Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019. 2019;:90. https://hdl.handle.net/21.15107/rcub_technorep_7406 .
Lazić, Anita M., Gak, Kristina G., Radovanović, Lidija D., Đorđević, Ivana S., "А crystallographic and theoretical study of intermolecular interactions of newly synthesized spirohydantoins" in Book of abstracts / Seventh Conference of the Young Chemists of Serbia, Belgrade, 2nd November 2019 (2019):90, https://hdl.handle.net/21.15107/rcub_technorep_7406 .