NAKSA GARNIDA ARFIE, 051111240 (2016) PENGARUH GUGUS METOKSI POSISI PARA PADA BENZALDEHIDA TERHADAP PERSENTASE HASIL SINTESIS N�-(p-METOKSIBENZILIDEN) ISONIKOTINOHIDRAZIDA. Skripsi thesis, UNIVERSITAS AIRLANGGA.

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Abstract

The research of the influence of methoxy group at para position of benzaldehyde on synthesis of N’-(p-methoxybenzylidene) isonicotinohydrazide through nucleophilic addition reaction had been carried out.The synthesis was carried out by reacting the isonicotinohydrazide (INH) with p-methoxybenzaldehyde. The mixture was refluxed for an hour using acetic acid glacial as a catalyst and monitored by TLC (methanol: chloroform=1:4) as mobile phase and on silica gel (60GF254) as stationary phase . The yields percentage of this compound was compared with N’-benzylidene isonicotinohidrazide, synthesized by reacting INH with benzaldehyde under the same method. The identification of the results were performed by FT-IR, UV, and 1H-NMR spectroscopy. The (E)-N’-benzylideneisonicotinohidrazide (59.03%, m.p. 200-201°C) and N’-(p-methoxybenzylidene)isonicotinohydrazide (61.69%, m.p. 166-167°C) were obtained as needle and colorless crystal. A statistical analysis of the yields by Independent T-Test showed that no significantly differences (α >0.05).The inductive effect from O atom of methoxy group, will withdraw electrons from aromatic ring because of its electronegativity. So that, carbonyl C atom more reactive of nucleophilic attack. On the contrary, resonance effect caused of lone pair electrons from O atom of methoxy group. This lone pair electrons will donate electron to the aromatic ring and cause various forms of resonance. Double bonds between the carbonyl C atom and C atom which directly attached to the aromatic ring are formed. This double bonds make carbonyl C atom less reactive of nucleophilic attack. The conclusion of the research was methoxy group on para position couldn’t increase or decrease the yield percentage of N’-benzylideneisonicotinohidrazide and N’-(p-methoxybenzylidene)isonicotinohydrazide because of inductive and resonance effect of the reaction.

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