Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives
Nema prikaza
Autori
Ratković, Zoran R.Novaković, Slađana B.
Bogdanović, Goran A.
Segan, Dejan
Vukićević, Rastko D.
Članak u časopisu
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular... interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved.
Ključne reči:
Ferrocene / 2-Alkylthiobenzoic acids / (2-Alkylthiobenzoyl)ferrocenes / Cyclic voltammetry / Crystal structure / C-H center dot center dot center dot pi interactionsIzvor:
Polyhedron, 2010, 29, 11, 2311-2317Finansiranje / projekti:
- Ministry of Science and Technological Development of the Republic of Serbia [142042, 142010]
DOI: 10.1016/j.poly.2010.04.034
ISSN: 0277-5387
WoS: 000280634300011
Scopus: 2-s2.0-77954621246
Kolekcije
Institucija/grupa
VinčaTY - JOUR AU - Ratković, Zoran R. AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Segan, Dejan AU - Vukićević, Rastko D. PY - 2010 UR - https://vinar.vin.bg.ac.rs/handle/123456789/3957 AB - The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved. T2 - Polyhedron T1 - Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives VL - 29 IS - 11 SP - 2311 EP - 2317 DO - 10.1016/j.poly.2010.04.034 ER -
@article{ author = "Ratković, Zoran R. and Novaković, Slađana B. and Bogdanović, Goran A. and Segan, Dejan and Vukićević, Rastko D.", year = "2010", abstract = "The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, (1)H and (13)C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations for three of them are also reported. Each of the three derivatives exhibits the intramolecular C-H center dot center dot center dot O interaction which involves the donor from the cyclopentadienyl (Cp) ring and the carbonyl oxygen as acceptor. This interaction favors the coplanar arrangement of the two moieties. The angles between the vectors coinciding the C-O bonds and the corresponding Cp planes are all below 6.4 degrees. Conventional hydrogen bonds do not exist in any of the three crystal structures but some weak intermolecular interactions of the C-H center dot center dot center dot, C-H center dot center dot center dot S and C-H center dot center dot center dot pi types have been found and analyzed in detail. Different geometrical parameters for these crystal structures as well as for 22 similar ones extracted from Cambridge Structural Database (CSD) have been compared and analyzed. (C) 2010 Elsevier Ltd. All rights reserved.", journal = "Polyhedron", title = "Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives", volume = "29", number = "11", pages = "2311-2317", doi = "10.1016/j.poly.2010.04.034" }
Ratković, Z. R., Novaković, S. B., Bogdanović, G. A., Segan, D.,& Vukićević, R. D.. (2010). Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives. in Polyhedron, 29(11), 2311-2317. https://doi.org/10.1016/j.poly.2010.04.034
Ratković ZR, Novaković SB, Bogdanović GA, Segan D, Vukićević RD. Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives. in Polyhedron. 2010;29(11):2311-2317. doi:10.1016/j.poly.2010.04.034 .
Ratković, Zoran R., Novaković, Slađana B., Bogdanović, Goran A., Segan, Dejan, Vukićević, Rastko D., "Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives" in Polyhedron, 29, no. 11 (2010):2311-2317, https://doi.org/10.1016/j.poly.2010.04.034 . .