AZO COUPLING OF 4-NITROPHENYLDIAZONIUM CHLORIDE WITH ALIPHATIC NUCLEOPHILES: AN INTEGRATED ORGANIC SYNTHESIS AND X-RAY CRYSTALLOGRAPHY EXPERIMENT

作者：Cunha Silvio^*; Marques Monique F; Rocha Valeria; Lariucci Carlito; Vencato Ivo

来源：Quimica Nova, 2013, 36(9): 1453-U217.

• enaminone
• azo dye
• solid state structure

This article describes an undergraduate experiment for the synthesis of p-nitrophenyldiazonium chloride and its coupling with acetylacetone and two enaminones, 4-phenylamino-pent-3-en-2-one and 4-amino-pent-3-en-2-one, in an adaptation of a previously reported synthetic protocol. The azo dyes 4-(E)-phenylamino-3-[(E)-2-(4-nitrophenylazo)]-3-penten-2-one and 4-(E)-amino-3-[(E)-2-(4-nitrophenylazo)]-3-penten-2-one were obtained, and the solid state structure of this latter azo compound was characterized by single crystal X-ray diffraction studies. This two-week integrated laboratory approach involves simple synthetic experiments and microwave chemistry in the organic laboratory plus crystallography analysis, suitable for novice students on undergraduate experimental chemistry courses.

• 出版日期2013