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Synthesis and characterization of a novel organic–inorganic hybrid salt and its application as a highly effectual Brønsted–Lewis acidic catalyst for the production of N , N ′‐alkylidene bisamides
Author(s) -
Zare Abdolkarim,
Monfared Fatemeh,
Sajadikhah Seyed Sajad
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6046
Subject(s) - chemistry , catalysis , lewis acids and bases , salt (chemistry) , thermogravimetric analysis , gravimetric analysis , yield (engineering) , infrared spectroscopy , brønsted–lowry acid–base theory , pyridine , fourier transform infrared spectroscopy , nuclear chemistry , inorganic chemistry , organic chemistry , chemical engineering , metallurgy , engineering , materials science
In this research, a novel organic–inorganic hybrid salt, namely, N 1 , N 1 , N 2 , N 2 ‐tetramethyl‐ N 1 , N 2 ‐bis(sulfo)ethane‐1,2‐diaminium tetrachloroferrate ([TMBSED][FeCl 4 ] 2 ) was prepared and characterized by Fourier‐transform infrared spectroscopy (FT‐IR), energy‐dispersive X‐ray spectroscopy (EDX), elemental mapping, field emission scanning electron microscopy (FE‐SEM), X‐ray diffraction (XRD), thermal gravimetric (TG), differential thermal gravimetric (DTG), and vibrating‐sample magnetometry (VSM) analyses. Catalytic activity of the hybrid salt was tested for the synthesis of N,N ′‐alkylidene bisamides through the reaction of benzamide (2 eq.) and aromatic aldehydes (1 eq.) under solvent‐free conditions in which the products were obtained in high yields and short reaction times. The catalyst was superior to many of the reported catalysts in terms of two or more of these factors: the reaction medium and temperature, yield, time, and turnover frequency (TOF). [TMBSED][FeCl 4 ] 2 is a Brønsted–Lewis acidic catalyst; there are two SO 3 H groups (as Brønsted acidic sites) and two tetrachloroferrate anions (as Lewis acidic sites) in its structure. Highly effectiveness of the catalyst for the synthesis of N,N ′‐alkylidene bisamides can be attributed to synergy of the Brønsted and Lewis acids and also possessing two sites of each acid.