Malaysian Journal of Analytical Sciences, Vol 27 No 3 (2023): 453 - 462

SYNTHESIS AND CHARACTERISATIONS OF NICKEL(II)–HYDRAZONE COMPLEX AS CATALYST IN SUZUKI REACTION

(Sintesis, dan Pencirian Nikel(II)– Hidrazon Kompleks Sebagai Pemangkin

dalam Tindak Balas Suzuki)

Aisyah Ahmad Fauzi¹, Norul Azilah Abdul Rahman^1,2, and Nur Rahimah Said^1*

¹School of Chemistry and Environment,

Faculty of Applied Sciences,

Universiti Teknologi MARA,

Cawangan Negeri Sembilan, Kampus Kuala Pilah,

72000 Kuala Pilah, Negeri Sembilan, Malaysia

²School of Chemistry and Environment,

Faculty of Applied Sciences Universiti Teknologi MARA,

40450 Shah Alam, Selangor, Malaysia

*Corresponding author: nurra1435@uitm.edu.my

Received: 24 October 2022; Accepted: 18 April 2023; Published: 23 June 2023

Abstract

Dichloro-N’-(3-chlorobenzylidene) benzohydrazide nickel(II) complex was successfully synthesised using 4-chloro-N’-(4-chlorobenzylidene) benzohydrazide ligand with nickel(II) chloride. The synthesised ligand and complex were characterised by various instruments including FTIR, ¹H NMR, ¹³CNMR, and UV-Vis spectroscopy. The preliminary complexation study between Ni²⁺cation and ligand showed that 1:1 stoichiometric formation corresponded to the metal-ligand ratio. The catalytic performance of the complex was tested using a Suzuki reaction between phenylboronic acid and four different aryl bromides (1-bromo-4-nitrobenzene, 4-bromoanisole, 4-bromoacetophenone, and bromobenzene) at different solvents and bases. The per cent (%) conversion rate of reactant to the product was determined using GC-FID. The best catalytic performance was found in the reaction between phenylboronic acid and 1-bromo-4-nitrobenzene using 0.5% mmol catalyst loading, methanol as a solvent, and K₂CO₃ as a base at temperature of 65°C within 2 h reaction time, giving a conversion rate of 81.86%. 

Keywords: hydrazone ligand, nickel (II)-hydrazone complex, Suzuki reaction

Abstrak

Kompleks dikloro-N’-(3-klorobenzilidena) benzohidrazida nikel(II) telah berjaya disintesis menggunakan ligan 4-kloro-N’-(4-klorobenzilidena) benzohidrazida dengan nikel(II) klorida. Ligan dan komplex yang disintesis dicirikan oleh pelbagai alat terdiri daripada FTIR, ¹HNMR, ¹³CNMR, dan spektroskopi UV-Vis. Kajian awal pembentukan kompleks antara kation Ni²⁺ dan ligan menunjukkan stoikiometri pembentukan ialah 1:1 sepadan dengan nisbah logam-ligan. Prestasi pemangkinan komplek telah diuji menggunakan tindak balas Suzuki antara asid fenilboronik dan empat aril bromida yang berbeza (1-bromo-4-nitrobenzena, 4-bromoanisol, 4-bromoacetofinon, dan bromobenzena) pada parameter yang berbeza seperti jenis pelarut dan bes. Peratus (%) kadar penukaran bahan tindak balas kepada produk ditentukan menggunakan GC-FID. Prestasi pemangkinan terbaik didapati dalam tindak balas antara asid fenilboronik dan 1-bromo-4-nitrobenzena dengan menggunakan pemuatan mangkin 0.5% mmol, metanol sebagai pelarut, K₂CO₃ sebagai bes pada suhu 65°C dalam masa tindak balas 2 jam memberi kadar penukaran sebanyak 81.86%.

Kata kunci: ligan hidrazon, kompleks nikel (II)-hidrazon, tindak balas Suzuki

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