The polar mechanism for the nitration of benzene with nitronium ion: ab initio structures of intermediates and transition states

Vernon D Parker; Tapas Kar; Donald Bethell

doi:10.1021/jo401775u

The polar mechanism for the nitration of benzene with nitronium ion: ab initio structures of intermediates and transition states

J Org Chem. 2013 Sep 20;78(18):9522-5. doi: 10.1021/jo401775u. Epub 2013 Sep 5.

Authors

Vernon D Parker¹, Tapas Kar, Donald Bethell

Affiliation

¹ Department of Chemistry and Biochemistry, Utah State University , Logan, Utah 84322-0300, United States.

PMID: 23971831
DOI: 10.1021/jo401775u

Abstract

The nitration of benzene by nitronium ion in the gas phase has been re-examined. New features have been revealed; in particular, three transition states have been detected along the reaction coordinate. These have been shown by IRC analysis to connect an initially formed π complex (pi1) to a σ complex (sig1) (via ts1), sig1 to sig2 (via ts2), and finally sig2 to the product (via ts3). Sig2 also connects to another isomeric σ complex sig3 (via sig23ts), which connects to sig4 (via sig34ts).

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Benzene / chemistry*
Ions / chemistry
Nitrogen Oxides / chemistry*
Quantum Theory*

Substances

Ions
Nitrogen Oxides
Benzene