New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one
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2014
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Three series of ferrocene containing 3-(arylthio)propan-1-ones (each of eight examples) have been synthesized by thia-Michael addition of the corresponding thiophenols to acryloylferrocene, 1-ferroceny1-3-phenylprop-2-en-1-one and 3-ferrocenyl-1-phenylprop-2-en-1-one promoted by the catalyst generated from a sacrificial zirconium anode. All the newly synthesized compounds (16 in total) were characterized by spectral data, whereas single crystal X-ray structure analysis was performed for 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one (1h), 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1 one (2h) and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one (3h). Molecular geometry and structural characteristics of three thiaketones (1h, 2h and 3h) were analysed and compared in detail. It was found that all three molecules do not form classical H-bonds and pi center dot center dot center dot pi interactions (regardless of the presence of 3 or 4 aromatic rings per a molecule). ...However, all three crystal structures abound in intermolecular C-H center dot center dot center dot pi interactions while 2h and 3h in addition form intramolecular C-H center dot center dot center dot pi as only evident interaction within the molecules. (C) 2013 Elsevier Ltd. All rights reserved.
Ključne reči:
Ferrocene / 3-(Arylthio)propan-1-ones / Crystal structure / Zirconium catalyst / Anodic dissolutionIzvor:
Polyhedron, 2014, 80, SI, 10-19Finansiranje / projekti:
- Nove elektrohemijske i hemijske metode u sintezi organskih jedinjenja od interesa za medicinu i hemiju materijala (RS-MESTD-Basic Research (BR or ON)-172034)
- Dizajniranje, sinteza, karakterizacija i procena praktične primene koordinacionih i organometalnih jedinjenja (RS-MESTD-Basic Research (BR or ON)-172014)
DOI: 10.1016/j.poly.2013.12.012
ISSN: 0277-5387
WoS: 000341348300003
Scopus: 2-s2.0-84905577753
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VinčaTY - JOUR AU - Stevanović, Dragana D. AU - Bogdanović, Goran A. AU - Vukićević, Rastko D. PY - 2014 UR - https://vinar.vin.bg.ac.rs/handle/123456789/98 AB - Three series of ferrocene containing 3-(arylthio)propan-1-ones (each of eight examples) have been synthesized by thia-Michael addition of the corresponding thiophenols to acryloylferrocene, 1-ferroceny1-3-phenylprop-2-en-1-one and 3-ferrocenyl-1-phenylprop-2-en-1-one promoted by the catalyst generated from a sacrificial zirconium anode. All the newly synthesized compounds (16 in total) were characterized by spectral data, whereas single crystal X-ray structure analysis was performed for 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one (1h), 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1 one (2h) and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one (3h). Molecular geometry and structural characteristics of three thiaketones (1h, 2h and 3h) were analysed and compared in detail. It was found that all three molecules do not form classical H-bonds and pi center dot center dot center dot pi interactions (regardless of the presence of 3 or 4 aromatic rings per a molecule). However, all three crystal structures abound in intermolecular C-H center dot center dot center dot pi interactions while 2h and 3h in addition form intramolecular C-H center dot center dot center dot pi as only evident interaction within the molecules. (C) 2013 Elsevier Ltd. All rights reserved. T2 - Polyhedron T1 - New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one VL - 80 IS - SI SP - 10 EP - 19 DO - 10.1016/j.poly.2013.12.012 ER -
@article{ author = "Stevanović, Dragana D. and Bogdanović, Goran A. and Vukićević, Rastko D.", year = "2014", abstract = "Three series of ferrocene containing 3-(arylthio)propan-1-ones (each of eight examples) have been synthesized by thia-Michael addition of the corresponding thiophenols to acryloylferrocene, 1-ferroceny1-3-phenylprop-2-en-1-one and 3-ferrocenyl-1-phenylprop-2-en-1-one promoted by the catalyst generated from a sacrificial zirconium anode. All the newly synthesized compounds (16 in total) were characterized by spectral data, whereas single crystal X-ray structure analysis was performed for 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one (1h), 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1 one (2h) and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one (3h). Molecular geometry and structural characteristics of three thiaketones (1h, 2h and 3h) were analysed and compared in detail. It was found that all three molecules do not form classical H-bonds and pi center dot center dot center dot pi interactions (regardless of the presence of 3 or 4 aromatic rings per a molecule). However, all three crystal structures abound in intermolecular C-H center dot center dot center dot pi interactions while 2h and 3h in addition form intramolecular C-H center dot center dot center dot pi as only evident interaction within the molecules. (C) 2013 Elsevier Ltd. All rights reserved.", journal = "Polyhedron", title = "New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one", volume = "80", number = "SI", pages = "10-19", doi = "10.1016/j.poly.2013.12.012" }
Stevanović, D. D., Bogdanović, G. A.,& Vukićević, R. D.. (2014). New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one. in Polyhedron, 80(SI), 10-19. https://doi.org/10.1016/j.poly.2013.12.012
Stevanović DD, Bogdanović GA, Vukićević RD. New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one. in Polyhedron. 2014;80(SI):10-19. doi:10.1016/j.poly.2013.12.012 .
Stevanović, Dragana D., Bogdanović, Goran A., Vukićević, Rastko D., "New ferrocene containing 3-(arylthio)propan-1-ones: Synthesis, spectral characterization and crystal structure of 3-[(4-chlorophenyl)thio]-1-ferrocenylpropan-1-one, 3-[(4-chlorophenyl)thio]-1-ferrocenyl-3-phenylpropan-1-one and 3-[(4-chlorophenyl)thio]-3-ferrocenyl-1-phenylpropan-1-one" in Polyhedron, 80, no. SI (2014):10-19, https://doi.org/10.1016/j.poly.2013.12.012 . .