Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

1693304

Reference Type

Journal Article

Title

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

Author(s)

Rodrigues, JAR; de Oliveira, AP; Moran, PJS; Custodio, R

Year

1999

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Volume

Issue

Page Numbers

6733-6738

Web of Science Id

WOS:000080579600002

URL

https://linkinghub.elsevier.com/retrieve/pii/S0040402099003208
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Abstract

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, (C) 1999 Elsevier Science Ltd. All rights reserved.

Keywords

nitration; nitric acid and derivatives; phenols; regioselection