Acoplamento de cloreto de 4-nitrofenildiazônio com nucleófilos alifáticos: experimento integrado de síntese orgânica e cristalografia de raios X

• Main Authors: Silvio Cunha, Monique F. Marques, Valéria Rocha, Carlito Lariucci, Ivo Vencato
• Format: Article
• Language: English
• Published: Sociedade Brasileira de Química 2013-01-01
• Series: Química Nova
• Subjects: enaminone; azo dye; solid state structure
• Online Access: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000900029&lng=en&tlng=en

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.