Electric Hindrance and Precursor Complexes in the Regiochemistry of Some Nitrations

• Francisco Sánchez-Viesca ^[1] ; María Reina Gómez Gómez ^[1] ; Martha Berros ^[1]
  1. [1] Universidad Nacional Autónoma de México

     Universidad Nacional Autónoma de México

     México

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 88, Nº 7, 2011, págs. 944-946
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • There are still gaps in the theory of supposedly well-known chemical reactions. For example, there is no explanation why there is a notorious preponderance of one of the expected isomers in some electrophilic aromatic substitutions. The preferred ortho orientation of acetyl nitrate has been used widely to obtain ortho nitro compounds; however, there is not causal explanation of this phenomenon. In this communication, an explanatory discussion is given to provide a complete theory on the regiochemistry of some of the mentioned reactions. To illustrate our theory, acetanilide, toluene, and anisole have been chosen as substrates in nitrations performed with nitric/sulfuric acid mixture and with acetyl nitrate.