Sains Malaysiana 46(5)(2017): 725–731

http://dx.doi.org/10.17576/jsm-2017-4605-07

Synthesis and Structural Characterization of 6-(N-Methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic Acid Methyl Ester Isomers

(Sintesis dan Pencirian Struktur Isomer 6-(N-Metil-piridina-2-ylkarbamoil)-piridina-2-karboksilik Asid Metil Ester)

MAISARA ABDUL KADIR*, NAFISAH MANSOR & UWAISULQARNI M. OSMAN

School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu Darul Iman, Malaysia

Diserahkan: 20 Julai 2016/Diterima: 24 Oktober 2016

ABSTRACT

A series of monoamide isomers have been successfully synthesised and characterised using combination of common spectroscopic techniques such Fourier Transform Infrared (FT-IR), ¹H and ¹³C Nuclear Magnetic Resonance (NMR) and Ultraviolet-visible (UV-vis). The monoamide compounds namely 6-(3-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L1), 6-(4-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L2), 6-(5-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L3) and 6-(6-methyl-pyridin-2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester (L4) were prepared from reaction between 6-(methoxycarbonyl)pyridine-2-carboxylic acid with 2-amino-N-methylpyridine (where N = 3, 4, 5 and 6) by using acyl chloride reaction. In this present studies, the synthesis and characterization of these compounds are discussed along with the inductive effects contributed by methyl substituted groups at the pyridine ring.

Keywords: Acyl chloride; inductive; isomers; monoamide; pyridine

ABSTRAK

Suatu siri isomer baru monoamida telah berjaya disintesis dan dicirikan menggunakan gabungan beberapa teknik spektroskopi seperti Fourier Penukar Inframerah (FTIR), ¹H dan ¹³C Resonans Magnet Nukleus (RMN) dan Ultra-lembayung boleh nampak (UV-vis). Sebatian yang dinamakan sebagai 6-(3-metil-piridin-2-ilkarbamoil)-piridina-2-karboksilik asid metil ester (L1), 6-(4-metil-piridin-2-ilkarbamoil)-piridina-2-karboksilik asid metil ester (L2), 6-(5-metil-piridin-2-ilkarbamoil)-piridina-2-karboksilik asid metil ester (L3) dan 6-(6-metil-piridin-2-ilkarbamoil)-piridina-2-karboksilik asid metil ester (L4) dihasilkan daripada tindak balas antara 6-(metoksikarbonil)piridin-2-karboksilik asid dengan 2-amino-N-metilpiridin (dengan N = 3, 4, 5 dan 6) menggunakan kaedah asil klorida. Dalam kajian ini, kaedah sintesis dan pencirian struktur sebatian berikut akan dibincangkan bersama kesan induktif yang disumbangkan oleh kumpulan penukarganti metil pada gegelang piridin.

Kata kunci: Asil klorida; induktif; isomer; monoamida; piridina

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*Pengarang untuk surat-menyurat; email: maisara@umt.edu.my