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Hydrogen and halogen bonding in the haloetherification products in chalcone
Author(s) -
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.
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619001025
Subject(s) - chalcone , halogen , halogen bond , hydrogen bond , chemistry , hydrogen , stereochemistry , organic chemistry , molecule , alkyl
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, C 21 H 24 Cl 2 O 3 , (2 S ,3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐methoxy‐1‐phenylpropan‐1‐one, C 20 H 22 Br 2 O 3 , and (2 S ,3 S )‐2‐bromo‐3‐(3‐ tert ‐butyl‐5‐bromo‐4‐hydroxyphenyl)‐3‐ethoxy‐1‐phenylpropan‐1‐one, C 21 H 24 Br 2 O 3 , 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.