Sintesis dan Analisis Struktur Senyawa 1,2-bis(benzilidena)hidrazin Tersubstitusi Gugus Hidroksi dan Metoksi

Setiawan, Agung Bagus (2026) Sintesis dan Analisis Struktur Senyawa 1,2-bis(benzilidena)hidrazin Tersubstitusi Gugus Hidroksi dan Metoksi. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Azina merupakan senyawa yang mengandung dua gugus azometina (C=N) yang dihubungkan oleh ikatan N-N, sehingga memiliki keragaman struktur dan berbagai aktivitas biologis. Untuk memperoleh senyawa azina secara lebih efisien dan ramah lingkungan, penelitian ini melaporkan sintesis 1,2-bis(benzilidena)hidrazin tersubstitusi gugus hidroksi dan metoksi menggunakan etanol sebagai pelarut, tanpa katalis dan tanpa pemanasan. Penelitian dilakukan dengan mereaksikan 20 mmol turunan benzaldehida berupa 4-hidroksi-3-metoksibenzaldehida (13a), 3-hidroksibenzaldehida (13b), 4-metoksibenzaldehida (13c), dan 2,4-dimetoksibenzaldehida (13d) dalam etanol dengan 10 mmol hidrazin hidrat (14) yang memberikan senyawa 1,2-bis((E)-4-hidroksi-3-metoksibenzilidena)hidrazin (8a) dengan yield 95,68%, 1,2-bis((E)-3-hidroksibenzilidena)hidrazin (8b) dengan yield 90,92%, 1,2-bis((E)-4-metoksibenzilidena)-hidrazin (8c) dengan yield 83,60%, dan 1,2-bis((E)-2,4-dimetoksibenzilidena)hidrazin (8d) dengan yield 88,56%. Spektrometer FTIR, NMR, dan analisis massa digunakan untuk menetapkan struktur senyawa hasil sintesis. Data spektrum ¹H-NMR keempat senyawa target menunjukkan sinyal proton azometina (-CH=N-) di daerah δ 8-9 ppm yang menjadi ciri khas struktur senyawa azina. Hasil ini diperkuat dengan data spektrum FTIR yang menunjukkan pita serapan C=N khas pada (ṽ) 1601 cm-1. Lebih lanjut, pengujian HRMS mengonfirmasi nilai m/z dan rumus molekul senyawa (8a-d) secara berurutan yaitu, m/z 301,1192 (C16H17N2O4) (8a), m/z 241,0985 (C14H13N2O2) (8b), m/z 269,1298 (C16H17N2O2) (8c), dan m/z 329,1496 (C18H21N2O4) (8d), yang telah sesuai dengan hasil perhitungan teoritis.
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Azines are compounds containing two azomethine (C=N) groups linked by an N-N bond, which endow them with structural diversity and a wide range of biological activities. To obtain azine compounds in a more efficient and environmentally friendly manner, this study reports the synthesis of hydroxyl- and methoxy-substituted 1,2-bis(benzylidene)hydrazines using ethanol as the solvent under catalyst-free and heating-free conditions. The synthesis was carried out by reacting 20 mmol of benzaldehyde derivatives, namely 4-hydroxy-3-methoxybenzaldehyde (13a), 3-hydroxybenzaldehyde (13b), 4-methoxybenzaldehyde (13c), and 2,4-dimethoxybenzaldehyde (13d), with 10 mmol of hydrazine hydrate (14) in ethanol, affording 1,2-bis((E)-4-hydroxy-3-methoxybenzylidene)hydrazine (8a) in 95.68% yield, 1,2-bis((E)-3-hydroxybenzylidene)hydrazine (8b) in 90.92% yield, 1,2-bis((E)-4-methoxybenzylidene)-hydrazine (8c) in 83.60% yield, and 1,2-bis((E)-2,4-dimethoxybenzylidene)hydrazine (8d) in 88.56% yield. The structures of the synthesized compounds were established using FTIR, NMR, and high-resolution mass spectrometry (HRMS). The 1H NMR spectra of all four target compounds exhibited characteristic azomethine (-CH=N-) proton signals in the δ 8-9 ppm regio, confirming the formation of the azine framework. These findings were further supported by the FTIR spectra, which displayed a characteristic C=N stretching absorption band at 1601 cm-1. Furthermore, HRMS analysis confirmed the molecular ions and molecular formulas of compounds (8a-d), with m/z values of 301,1192 (C16H17N2O4) for (8a), 241,0985 (C14H13N2O2) for (8b), 269,1298 (C16H17N2O2) for (8c), and 329,1496 (C18H21N2O4) for (8d), all of which are in good agreement with their calculated theoretical values.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Azina, benzilidena hidrazin, kondensasi, sintesis ramah lingkungan, azine, benzylidenehydrazine, condensation, green synthesis
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD481 Chemical structure.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Agung Bagus Setiawan
Date Deposited:	05 Aug 2026 02:43
Last Modified:	05 Aug 2026 02:43
URI:	http://repository.its.ac.id/id/eprint/143769

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