Hydrogen and halogen bonding in the haloetherification products in chalcone. Issue 3 (19th February 2019)

• Record Type: Journal Article
• Authors: Asgarova, Aytan R.; Khalilov, Ali N.; Brito, Ivan; Maharramov, Abel M.; Shikhaliyev, Namiq G.; Cisterna, Jonathan; Cárdenas, Alejandro; Gurbanov, Atash V.; Zubkov, Fedor I.; Mahmudov, Kamran T.
• Is Part Of: Acta crystallographica. Volume 75:Issue 3(2019)
• Page Start: 342
• Page End: 347
• Publication Date: 2019-02-19
• Subjects: noncovalent interactions -- crystal structure -- chalcone -- haloetherification -- NCI -- hydrogen bonding -- halogen bonding; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229619001025
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The reaction of 3‐(3, 5‐di‐ tert ‐butyl‐4‐hydroxyphenyl)‐1‐phenylprop‐2‐en‐1‐one with HCl or HBr in MeOH of EtOH leads to the haloetherification products 3‐(3‐ tert ‐butyl‐5‐halo‐4‐hydroxyphenyl)‐2‐halo‐3‐alkoxy‐1‐phenylpropan‐1‐ones. Both intermolecular hydrogen and halogen bonds were found in the crystal structures of the haloetherification products of chalcone. Abstract : Cooperative action of hydrogen and halogen bonding in the reaction of 3‐(3, 5‐di‐ tert ‐butyl‐4‐hydroxyphenyl)‐1‐phenylprop‐2‐en‐1‐one with HCl or HBr in alcohol medium under microwave irradiation (20 W, 80 °C, 10 min) allows the isolation of the haloetherification products (2 S, 3 S )‐3‐(3‐ tert ‐butyl‐5‐chloro‐4‐hydroxyphenyl)‐2‐chloro‐3‐ethoxy‐1‐phenylpropan‐1‐one, C21 H24 Cl2 O3, (2 S, 3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐methoxy‐1‐phenylpropan‐1‐one, C20 H22 Br2 O3, and (2 S, 3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐ethoxy‐1‐phenylpropan‐1‐one, C21 H24 Br2 O3, in good yields. Both types of noncovalent interactions, e.g. hydrogen and halogen bonds, are formed to stabilize the obtained products in the solid state.