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Synthesis and Spectroscopic Studies of p-Nitroanilide Derivatives Using
Dicyclohexylcarbodiimide Coupling Methods
Nur Shuhaila Haryani binti Abd Haris
Supervisor: Dr Maisara binti Abdul Kadir
Bachelor of Science (Chemical Sciences)
School of Fundamental Science
Peptide-p-nitroanilide is obtained by using dicyclohexylcarbodiimide (DCC) as coupling
agent. In this approach, a new p-nitroanilide derivative namely tert-butyl(3-methyl-1-
((4-nitrophenyl)amino)-1-oxobutan-2-yl)carbamate was successfully synthesized. This
compound was characterized by spectroscopic techniques such as Fourier Transform
Infrared (FTIR), UV-Vis, 1 H and 13 C Nuclear Magnetic Resonance (NMR). From FTIR
spectrum, several important peaks were observed at 3362.34 cm -1 , 1630.45 cm -1 and
1350.00 cm -1 which assigned for N-H, C=O and N-O, respectively. Based on UV-
Vis spectrum, the C=O and NO2 signals were indicated at 375 nm, representing
electron transition to *. Meanwhile, the 1 H NMR shows the present of NH
resonances at 8.215 ppm and 6.794 ppm. The aromatic protons were identified at
range 7.838 – 8.293 ppm while in 13 C NMR spectrum, the resonances for carbon atoms
at benzyl ring were observed at range 112.39 – 135.61 ppm. Despite of several
attempts to produce p-nitroanilide derivatives, the reaction led to formation of tertbutyl(3-methyl-1-((4-nitrophenyl)amino)-1-oxobutan-2-yl)carbamate
only.
441 | U M T U N D E R G R A D U A T E R E S E A R C H D A Y 2018