Synthesis and structure of fluorinated (Benzo[d]imidazol-2-yl)methanols: Bench compounds for diverse applications

Synthesis and structure of fluorinated (Benzo[d]imidazol-2-yl)methanols: Bench compounds for diverse applications Full article

Journal

Crystals
ISSN: 2073-4352

Output data

Year: 2020, Volume: 10, Number: 9, Article number : 786, Pages count : 16 DOI: 10.3390/cryst10090786

Tags

1D, 2D, and 3D structures; Crystal structure; Fluorinated benzimidazoles; H-bonding; Heterocyclization; Polyfluorinated 1,2-diaminobenzenes

Authors

Romanov Vasily ^1,2 , Tretyakov Evgeny ¹ , Selivanova Galina ¹ , Li Jiayao Li ^1,2 , Bagryanskaya Irina ¹ , Makarov Alexander ¹ , Luneau Dominique ³

Affiliations

1	(Scopus) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, Novosibirsk, 630090, Russian Federation
2	(Scopus) Department of Natural Sciences, Novosibirsk State University, 2 Pirogova Str., Novosibirsk, 630090, Russian Federation
3	(Scopus) Campus de La Doua, Universit? Claude Bernard Lyon-1, Villeurbanne CEDEX, 69622, France

A simple and general approach to the synthesis (from commercial precursors) of eight out of nine possible (benzo[d]imidazol-2-yl)methanols fluorinated on the benzene ring is reported. Molecular and crystalline structures of most compounds were solved by X-ray diffraction analysis. This made it possible to reveal the influence of the number and arrangement of fluorine atoms in the benzene cycle on the formation of intermolecular hydrogen bonds. It was found that the more fluorine atoms are present in a compound, the higher the dimensionality of the H-bonded structure is. Moreover, the presence of fluorine atoms in the synthesized compounds leads to the emergence of C–F … π interactions affecting crystal packing. The synthesized fluorinated (benzo[d]imidazol-2-yl)methanols may serve as excellent bench compounds for the synthesis of a systematic series of fluorine-containing derivatives to study structure–property correlations in various fields of research from medicine to materials science. © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Romanov V. , Tretyakov E. , Selivanova G. , Li J.L. , Bagryanskaya I. , Makarov A. , Luneau D.
Synthesis and structure of fluorinated (Benzo[d]imidazol-2-yl)methanols: Bench compounds for diverse applications

Crystals. 2020. V.10. N9. 786 :1-16. DOI: 10.3390/cryst10090786 WOS Scopus РИНЦ

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Published online:

Sep 4, 2020

Web of science	WOS:000581975100001
Scopus	2-s2.0-85090267300
Elibrary	45360584
OpenAlex	W3083166737