Malaysian Journal of Analytical Sciences Vol 23 No 2 (2019): 189 - 196

SYNTHESIS AND CHARACTERISATION OF

N-ANALINEFERROCENYLAMIDE VIA CARBODIIMIDE COUPLING

(Sintesis dan Pencirian N-Analineferosenilamida melalui Gandingan Silang Karbodiimida)

Ken Min Liew¹, Tei Tagg¹, Wan M. Khairul^1,2*

¹School of Fundamental Science

²Advanced Nano Materials (ANoMa) Research Group, School of Fundamental Science

Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu, Malaysia

*Corresponding author: wmkhairul@umt.edu.my

Received: 24 February 2019; Accepted: 24 March 2019

Abstract

Ferrocene is an orthodox organometallic complex. This “sandwich compound” was found to have great flexibility in chemical reactions. The use of ferrocenyl derivatives branches into various interesting fields especially for biological applications. Derivatives of ferrocenylamides are of great interest in the field of medicine and biology researches, due to their ability to bind with various biomolecules, i.e. DNA. Thus, a simple yet effective method in the formation of ferrocenylamide derivatives is desirable. Ferrocene is stable in both aqueous and aerobic media, it also has a certain degree of resistance to thermal degradation, and hence the synthesis of ferrocenyl derivatives via carbodiimide coupling is possible. In this work, N-analineferrocenylamide was synthesised from 3-(ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine (EDC) coupling of ferrocenecarboxylic acid and p-phenylenediamine. This synthesis approach is a simple and easy one-pot reaction without the need of tedious conditions and has a good product yield.

Keywords: ferrocene, amide, EDC coupling

Abstrak

Ferosena merupakan kompleks organologam yang ortordoks. “Sebatian sandwich” ini didapati mempunyai pelbagai kebolehan di dalam tindakbalas kimia. Pengunaan terbitan-terbitan ferosena terjangkau di dalam pelbagai bidang yang menarik terutamanya dalam aplikasi biologi. Terbitan-terbitan ferosenilamida telah menarik minat yang mendalam dalam kajian bidang perubatan dan biologi, berdasarkan keupayaannya untuk terikat dengan pelbagai biomolekul seperti DNA. Justeru itu, kaedah yang ringkas dan efektif dalam pembentukan terbitan-terbitan ferosenilamida telah menjadi keutamaan. Ferosena adalah stabil di dalam kedua-dua media akues dan aerobik, ia juga mempunyai darjah keupayaan rintangan yang tertentu terhadap penguraian terma, yang telah memungkinkan sintesis terbitan-terbitan ferosena melalui gandingan silang karbodiimida. Di dalam kajian ini, N-analinaferosenilamida telah disintesiskan daripada gandingan silang 3-(etiliminometilenaamino)-N,N-dimetilpropan-1-amina (EDC) terhadap asid karboksilikferosena dan p-fenilenadiamina. Pendekatan sintesis adalah tindakbalas satu pot yang ringkas dan mudah tanpa memerlukan keadaan yang remeh dan berjaya menghasilkan hasilan yang baik.

Kata kunci: ferosena, amida, gantian silang EDC

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