Issue 10, 2005

Protonated nitro group: structure, energy and conjugation

Abstract

Structure of protonated nitro compounds was investigated by calculations at the levels MP2(FC)/6-311++G(2d,2p)//MP2(FC)/6-311++G(2d,2p) (nitromethane and reference compounds) or B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p) (nitrobenzene and its 18 meta- and para-substituted derivatives). The group NO2H+ reveals many similarities with the isoelectronic group CO2H as the preferred conformation, conformational equilibrium, and stabilization by interaction (resonance) within the group quantified by means of isodesmic reactions. However, there is a difference in the interaction with donor groups (for instance in 4-nitroaniline) that is much stronger with NO2H+ than with CO2H. This interaction may be called resonance and may be described by standard resonance formulas, but these formulas predict only partially the geometry and cannot explain the great interaction energy.

Graphical abstract: Protonated nitro group: structure, energy and conjugation

Article information

Article type
Paper
Submitted
10 Feb 2005
Accepted
16 Mar 2005
First published
14 Apr 2005

Org. Biomol. Chem., 2005,3, 1838-1843

Protonated nitro group: structure, energy and conjugation

O. Exner and S. Böhm, Org. Biomol. Chem., 2005, 3, 1838 DOI: 10.1039/B502152A

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