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TIP. Revista especializada en ciencias químico-biológicas
versión impresa ISSN 1405-888X
TIP vol.9 no.1 Ciudad de México jun. 2006
Artículos originales
Espectroscopía y teoría de la regioquímica en la nitración de las benzopiridinas
Spectroscopy and regiochemistry theory in the benzopyridines nitration
1Facultad de Química, División de Estudios de Posgrado, UNAM. Ciudad Universitaria, CP. 04510, México, D.F.
En la presente comunicación se da una explicación teórica de la regioquímica observada en la nitración de las benzopiridinas, así como de los rendimientos relativos de los productos obtenidos. Se hizo una revisión de los métodos de preparación y de la espectroscopia de los compuestos estudiados. Un estudio cuidadoso de los espectros de RMN de 1H reveló la existencia en estos nitro compuestos de puentes de hidrógeno, del tipo C-H--'0-N=0, localizándose el átomo de hidrógeno en la posición peri al grupo nitro. La presencia de estas ligaduras secundarias explica los corrimientos a campo bajo observados en las señales de (dichos protones. Se determinaron los espectros de masas de la 5-nitro- y de la 8-nitroquinolina y se proponen los mecanismos de fragmentación de las rupturas típicas.
Palabras Clave: Espectrometría de masas; nitroquinolinas; nitroisoquinolinas; puentes de hidrógeno; resonancia magnética nuclear
In this communication we provide a theoretical explanation to the regiochemistry in the nitration of the benzopyridines as well as to the relative yields of the obtained products.
A review of the preparation procedures of the compounds under study is given, as well as the related spectroscopy. A careful study of 1 H NMR spectra revealed the existence of hydrogen bonds in these compounds. They are of the type С-Η-0-N=0, the hydrogen being at peri position to the nitro group. The existence of these bonds explains the down-field shifts observed in the signals of the involved protons.
The mass spectra of 5-nitro- and 8-nitroquinoline were determined. The fragmentation mechanisms of the typical ruptures are advanced.
Key Words: Hydrogen bonds; mass spectrometry; nitroquinolines; nitroisoquinolines; nuclear magnetic resonance
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Recibido: 23 de Febrero de 2006; Aprobado: 18 de Mayo de 2006