Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas
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2020
Authors
Minić, Aleksandra
Novaković, Slađana B.

Bogdanović, Goran A.

Bugarinović, Jovana P.

Pešić, Marko S.

Todosijević, Anka
Ilić-Komatina, Danijela
Damljanović, Ivan S.

Stevanović, Dragana D.

Article (Published version)

© 2019 Elsevier Ltd
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The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very dif...ferent crystal packing. © 2019 Elsevier Ltd
Keywords:
Ferrocene / Six-membered cyclic ureas / Atropoisomerism / Characterization / Crystal structureSource:
Polyhedron, 2020, 177, 114316-Funding / projects:
- Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-172034)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1016/j.poly.2019.114316
ISSN: 0277-5387
WoS: 000518876600031
Scopus: 2-s2.0-85078589201
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VinčaTY - JOUR AU - Minić, Aleksandra AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Bugarinović, Jovana P. AU - Pešić, Marko S. AU - Todosijević, Anka AU - Ilić-Komatina, Danijela AU - Damljanović, Ivan S. AU - Stevanović, Dragana D. PY - 2020 UR - https://vinar.vin.bg.ac.rs/handle/123456789/8808 AB - The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd T2 - Polyhedron T1 - Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas VL - 177 SP - 114316 DO - 10.1016/j.poly.2019.114316 ER -
@article{ author = "Minić, Aleksandra and Novaković, Slađana B. and Bogdanović, Goran A. and Bugarinović, Jovana P. and Pešić, Marko S. and Todosijević, Anka and Ilić-Komatina, Danijela and Damljanović, Ivan S. and Stevanović, Dragana D.", year = "2020", abstract = "The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd", journal = "Polyhedron", title = "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas", volume = "177", pages = "114316", doi = "10.1016/j.poly.2019.114316" }
Minić, A., Novaković, S. B., Bogdanović, G. A., Bugarinović, J. P., Pešić, M. S., Todosijević, A., Ilić-Komatina, D., Damljanović, I. S.,& Stevanović, D. D.. (2020). Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron, 177, 114316. https://doi.org/10.1016/j.poly.2019.114316
Minić A, Novaković SB, Bogdanović GA, Bugarinović JP, Pešić MS, Todosijević A, Ilić-Komatina D, Damljanović IS, Stevanović DD. Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron. 2020;177:114316. doi:10.1016/j.poly.2019.114316 .
Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Bugarinović, Jovana P., Pešić, Marko S., Todosijević, Anka, Ilić-Komatina, Danijela, Damljanović, Ivan S., Stevanović, Dragana D., "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas" in Polyhedron, 177 (2020):114316, https://doi.org/10.1016/j.poly.2019.114316 . .