Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas

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...

Keywords:

Ferrocene / Six-membered cyclic ureas / Atropoisomerism / Characterization / Crystal structure

Source:
Polyhedron, 2020, 177, 114316-

Funding / projects:

DOI: 10.1016/j.poly.2019.114316

ISSN: 0277-5387

WoS: 000518876600031

Scopus: 2-s2.0-85078589201

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TY - 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 . .