Sintesis Senyawa Hidrazon Berbasis Trans-sinamaldehida Dan Para-metoksisinamaldehida

Seviani, Winda (2025) Sintesis Senyawa Hidrazon Berbasis Trans-sinamaldehida Dan Para-metoksisinamaldehida. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa hidrazon dengan gugus azometin (‒NHN=CH‒) yang terikat pada cincin aril dapat diperoleh melalui reaksi kondensasi antara aldehida aromatik dengan amina primer. Penelitian ini melaporkan sintesis senyawa hidrazon 1a-d dan 2a-e berbasis trans-sinamaldehida dan para-metoksisinamaldehida. Sintesis senyawa hidrazon berbasis trans-sinamaldehida dilakukan antara trans-sinamaldehida 3 dengan fenil hidrazin 5, asam 2-tiofenakarboksilat hidrazida 6, asam 4-piridinkarboksilat hidrazida 7, dan 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 8. Sedangkan sintesis senyawa hidrazon berbasis para-metoksisinamaldehida dilakukan antara para-metoksisinamaldehida 4 dengan hidrazida 5-8 dan 2-(4-formil-2-etoksifenoksi)asetohidrazida 9. Senyawa hidrazon berbasis trans-sinamaldehida yang diperoleh berupa 1-fenil-2-(3-fenilalillidena)hidrazin 1a, N-(3-fenilalilidena)tiofena-2-karbohidrazida 1b, N-(3-fenilalilidena)isonikotinohidrazida 1c, dan 2-((4-metil-2-okso-dihidro-2H-kromen-7-il)oksi)-N’-(3-fenilalilidena)asetohidrazida 1d masing-masing diperoleh dengan yield 31,65%, 74,74%, 52,85%, dan 90,38%. Lebih lanjut, senyawa hidrazon berbasis para-metoksisinamaldehida yang didapatkan adalah 3-(4-metoksifenil)-alilidena-2-fenilhidrazin 2a, N'-(3-(4-metoksifenil)alilidena)tiofena-2-karbo-hidrazida 2b, N'-(3-(4-metoksi-fenil)alilidena)isonikotinohidrazida 2c, N'-(3-(4-metoksifenil)alilidena)-2-((4-metil-2-okso-dihidro-2H-kromen-7-il)oksi)aseto-hidrazida 2d, dan 2-(4-formil-2-metoksifenoksi)-N'-(3-(4-metoksifenil)alilidena)-asetohidrazida 2e dengan yield masing-masing sebesar 35,94%, 47,54%, 83,28%, 87,74%, 93,34%. Senyawa hasil sintesis diuji kemurnian dengan KLT sistem tiga eluen, KLT dua dimensi, dan uji titik leleh. Struktur seluruh senyawa hasil sintesis diidentifikasi dengan spektroskopi FTIR dan NMR serta analisis LCMS-MS.
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Hydrazone compounds with an azomethine group (‒NHN=CH‒) attached to the aryl ring can be obtained through a condensation reaction between heated aldehyde and primary amine. This study reports the synthesis of hydrazone compounds 1a-d and 2a-e based on trans-cinnamaldehyde and para-methoxycinnamaldehyde. Synthesis of trans-cinnamaldehyde-based hydrazone compounds was carried out between trans-cinnamaldehyde 3 with phenyl hydrazine 5, 2-thiophenecarboxylic acid hydrazide 6, 4-pyridinecarboxylic acid hydrazide 7, and 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 8. Meanwhile, the synthesis of hydrazone-based compounds para-methoxynamaldehyde is carried out between para-methoxynamaldehyde 4 with hydrazide 5-8 and 2-(4-formyl-2-methoxyphenoxy)acetohydrazide 9. The trans-cinnamaldehyde based hydrazone compound obtained is 1-phenyl-2-(3-phenylalylidene)hydrazine 1a, N-(3-phenylallylidene)thiophene-2-carbohydrazide 1b, N-(3-phenylallylidene)isonicotinohydrazide 1c, and 2-((4-methyl-2-oxo-dihydro-2H-chromen-7-yl)oxy)-N'-(3-phenylallylidene)acetohydrazide 1d was respectively obtained by yield 31.65%, 74.74%, 52.85%, and 90.38%. Furthermore, the para-methoxynamaldehyde based hydrazone compounds obtained were 3-(4-methoxyphenyl)allylidene-2-phenylhydrazine 2a, N'-(3-(4-methoxyphenyl)allyl-idene)thiophene-2-carbohydrazide 2b, N'-(3-(4-methoxy-phenyl)allylidene)iso-nicotinohydrazide 2c, N'-(3-(4-methoxyphenyl)allylidene)-2-((4-methyl-2-oxo-dihydro-2H-chromen-7-yl)oxy)acetohydrazide 2d, and 2-(4-formyl-2-methoxy-phenoxy)-N'-(3-(4-methoxyphenyl)allylidene)acetohydrazide 2e with a respective yield of 35.94%, 47.54%, 83.28%, 87.74%, 93.34%. The purity of the synthesized compounds was tested using three-eluent TLC system, two-dimensional TLC, and melting point test. The structures of all synthesized compounds were identified using FTIR and NMR spectroscopy as well as LCMS-MS analysis.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	hydrazones, trans-cinnamaldehyde, para-methoxycinnamaldehyde, hidrazon, trans-sinamaldehida, para-metoksisinamaldehida
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Winda Seviani
Date Deposited:	07 Feb 2025 06:33
Last Modified:	07 Feb 2025 06:33
URI:	http://repository.its.ac.id/id/eprint/118544

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