Reaksi Substitusi Nukleofilik Asil Klorida Dengan Nukleofil Vanililamina

Karimah, Iffah (2023) Reaksi Substitusi Nukleofilik Asil Klorida Dengan Nukleofil Vanililamina. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Asil klorida merupakan salah satu turunan asam karboksilat, dengan reaksi utama berupa reaksi substitusi asil nukleofilik. Vanililamina (3) mempunyai gugus amina primer dan gugus hidroksi tersier yang dapat berperan sebagai nukleofil. Reaksi vanililamina (3) dengan berbagai jenis hasil asil klorida pada rasio sekitar 2:1 atau 1:1 dilaporkan diperoleh kapsaisin (4a-b) dan berbagai analognya (7a-e, 10a-l, 12a-h, 14a-e, 16, 18), hal ini menunjukkan yang berperan sebagai nukleofil adalah gugus amina primer pada vanililamina (3). Kapsaisin (4a) merupakan zat pedas utama yang terdapat pada cabai, dan analog kapsaisin (10c-i, 11a-h) menunjukkan aktivitas antibakteri. Reaksi asil klorida (17) dengan analog kapsaisin (18) diperoleh senyawa (19) yang menunjukkan aktivitas terhadap strain-strain baru bakteri Staphylocccus aureus yang lebih baik dari pada antibiotika kanamisin. Penelitian ini mendapatkan bahwa gugus amina primer dan alkohol tersier pada vanililamina (3) dapat bereaksi dengan asil halida berupa butiril klorida (20a), pentanoil klorida (20b), isobutiril klorida (20c) ketika reaksi dilakukan pada rasio 2:1 sehingga masing-masing diperoleh senyawa-senyawa yang merupakan analog senyawa (19). Reaksi yang melibatkan butiril klorida (20a) diperoleh 4-(butiramidometil)-2-metoksifenil butirat (24a) dengan rendemen 93%, reaksi yang melibatkan pentanoil klorida (20b) diperoleh 2-metoksi-4-(pentaamidometil)phenil pentanoat (24b) dengan rendemen 93%, sedangkan reaksi yang melibatkan isobutiril klorida (20c) diperoleh 2-metoksi-4-((3-metilbutanamido)metil)phenil 3-metilbutanoat (24c) dengan rendemen 81%. Asil halida berupa 3,3-dimetilbutiril klorida (20d) lebih sterik dari pada asil halide (20a-c) sehingga hanya gugus amina primer vanililamina (3) yang bereaksi sedangkan gugus alkohol tersier tidak bereaksi sehingga diperoleh analog kapsaisin berupa N-(4-hidroksi-3-metoksibenzil)-3,3-dimetilbutanamida (23d) dengan rendemen 84%.
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Acyl chloride is a carboxylic acid derivative, with the main reaction being a nucleophilic acyl substitution reaction. Vanilylamine (3) has a primary amine group and a tertiary hydroxy group that can act as a nucleophile. The reaction of vanilylamine (3) with various types of acyl chlorides yields at ratios of about 2:1 or 1:1 reported to yield capsaicin (4a-b) and various analogues thereof (7a-e, 10a-1, 12a-h, 14a-e, 16 , 18), this shows that the primary amine group in vanilylamine acts as a nucleophile (3). Capsaicin (4a) is the main pungent substance found in chili peppers, and its analogues (10c-i, 11a-h) show antibacterial activity. The reaction of acyl chloride (17) with capsaicin analogue (18) yielded compound (19) which showed better activity against new strains of Staphylocccus aureus than the antibiotic kanamycin. This study found that the primary amine groups and tertiary alcohols in vanilylamine (3) can react with acyl halides in the form of butyl chloride (20a), pentanoyl chloride (20b), isobutyryl chloride (20c) when the reaction is carried out at a ratio of 2:1 so that each compounds which are analogous compounds (19) were obtained. The reaction involving butyryl chloride (20a) obtained 4-(butyramidomethyl)-2-methoxyphenyl butyrate (24a) in a yield of 93%, the reaction involving pentanoyl chloride (20b) obtained 2-methoxy-4-(pentaamidomethyl)phenyl pentanoate (24b) with a yield of 93%, while the reaction involving isobutyryl chloride (20c) obtained 2-methoxy-4-((3-methylbutanamido)methyl)phenyl 3-methylbutanoate (24c) with a yield of 81%. The acyl halide in the form of 3,3-dimethylbutyryl chloride (20d) is more steric than the acyl halide (20a-c) so that only the primary amine group vanilylamine (3) reacts while the tertiary alcohol group does not react so that the capsaicin analogue in the form of N-(4- hydroxy-3-methoxybenzyl)-3,3-dimethylbutanamide (23d) with a yield of 84%.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Acyl chloride, vanillylamine hydrochloride, nucleophilic acyl substitution, asil klorida, vanililamina hidroklorida, subtitusi nukleofilik
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Iffah Karimah
Date Deposited:	11 Aug 2023 00:51
Last Modified:	11 Aug 2023 00:51
URI:	http://repository.its.ac.id/id/eprint/104249

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