Dual Chalcogen-bonding interactions for the conformational control of urea

06 April 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Dual chalcogen-bonding interactions is proposed as a novel means for the conformational control of urea derivatives. The formation of a chalcogen-bonding interaction at both sides of the urea carbonyl group was unambiguously confirmed by X-ray diffraction and natural bond orbital (NBO) analysis via DFT calculations. By virtue of this dual interaction, urea derivatives that bear chalcogen atoms (X = S and Se) adopt a planar structure via the carbonyl oxygen (O) with an X•••O•••X arrangement on the same side of the molecule. The rigidity of the conformational lock was evaluated using the molecular arrangement in the crystal and the rotational barrier of benzochalcogenophene ring, which indicated a stronger conformational lock in benzoselenophene than in benzothiophene urea derivatives. Furthermore, the acidity of the urea derivatives increases according to the Lewis-acidic properties of the chalcogen-bonding interactions, whereby benzoselenophene urea is more acidic than benzothiophene urea. Tweezer-shaped urea derivatives were prepared, and their stereostructure proved the viability of the conformational control for defining the location of the substituents on the urea framework.

Keywords

Chalcogen-bonding interaction
urea
conformational control

Supplementary materials

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Description
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Title
Electronic Supplementary Information
Description
Experimental procedures, spectroscopic and X-ray data for all new compounds, and computational data
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