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Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel

1999; Elsevier BV; Volume: 55; Issue: 22 Linguagem: Inglês

10.1016/s0040-4020(99)00320-8

1464-5416

J. Augusto R. Rodrigues, Antonio Pedro de Oliveira Filho, Paulo J. S. Moran, Rogério Custódio,

Analytical Chemistry and Sensors

The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six-center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation.