SYNTHESIS AND CHARACTERISATION OF

NEW SCHIFF BASE COMPOUNDS OF

N-ETHYL-2-(2-HYDROXY-3-

METHOXYBENZALDENE)HYDRAZINECARBOTHIOAMIDE AND

2-(2,3-DIHYDOXYBENZYLIDENDE)-N-

ETHYLHYDRAZINECARBOTHIOAMIDE

ABSTRACT

In this study, two new Schiff bases: N-ethyl-2-(2-hydroxy-3-

methoxybenzylidene)hydrazinecarbothioamide (A1) and 2-(2,3-

dihydroxybenzylidene)-N-ethylhydrazinecarbothioamide (A2) were

synthesised by reacting 4-ethyl-3-thiosemicarbazide with 2-hydroxy-3-

methoxybenzaldehyde; and 4-ethyl-3-thiosemicarbazide with 2,3-

dihydroxybenzaldehyde in a 1:1 molar ratio, acid catalysed reaction and

under reflux in ethanol. The stage of completion of the reaction was

observed via thin layer chromatography, TLC. The percentage yields of

both imines were within 50 – 84%. Synthesised compounds were

characterised by FT-IR, ¹H and ¹³C NMR. Analysis by 2D NMR (COSY,

HMQC and HMBC) spectroscopy and DEPT-135 was conducted to further

confirm the structure of A1. Results show that the proposed structures of the

Schiff bases were supported with their spectroscopic data.

Keywords: Schiff base, FT-IR, ¹H NMR, ¹³C NMR, 2D NMR, DEPT-135.

 SINTESIS DAN PENCIRIAN DUA SEBATIAN BES SCHIFF BARU

N-ETIL-2-(2-HIDROKSI-3-

METOKSIBENZILIDENA)HIDRAZINAKARBOTIOAMIDA AND 2-

(2,3-DEHIDROKSIBENZILIDENA)-N- ETIL

HIDRAZINAKARBOTIOAMIDA

ABSTRAK

Dalam kajian ini, dua bes Schiff baru: N-etil-2-(2-hidroksi-3-

metoksibenzilidena)hidrazinakarbothioamida (A1) dan 2-(2,3-

dehidroksibenzalidena)-N-etilhidrazinakarbotioamida (A2) telah

disintesiskan secara tindakbalas 4-etil-3-tiosemikarbazida dengan 2-

hidroksi-3-metoksibenzaldehid; dan 4-etil-3-tiosemikarbazida dengan 2,3-

dehidoksibenzaldehid dalam nisbah 1: 1 molar dan dimangkinkan oleh asid

secara refluks dalam larutan ethanol. Masa tamat tindakbalas campuran

diperhatikan menggunakan kaedah kromatografi lapisan nipis. Peratusan

hasil kedua-dua imina adalah 50-84%. Sebatian yang disintesis telah

dicirikan oleh FT-IR, ¹H dan ¹³C NMR. Analisis secara 2D NMR (COSY,

HMQC dan HMBC) spektroskopi dan DEPT-135 telah dijalankan untuk

pengesahan lanjut struktur A1. Hasil kajian menunjukkan bahawa struktur

cadangan bes Schiff disokong dengan data spektroskopi tersebut.

Kata kunci: bes Schiff, FT-IR, ¹H NMR, ¹³C NMR, 2D NMR, DEPT-135.