5-Nitroanilines structure relationship

Assmann N et al., Genotoxic activity of important nitrobenzenes and nitroanilines in the Ames test and their structure-activity relationship, Mut. Res., 395, 139, 1997. 

Structure-Property Relationships, The studies aimed at construction of the (8 scale and related investigations have uncovered some interesting relationships between indicator structures and solvatochromic effects. It was found (78c, 134) for example, that 4-nitroaniline (1) forms two hydrogen bonds to HBA solvents, that the ratio of the hydrogen bond strengths is about 1.5/1, and that the ratio of the bathochromic spectral effects is 1 /(0.93 0.13). Comparable effects have also been observed with 3-nitroaniline (12). 

The polarizability and first hyperpolarizability of p-nitroaniline and its methyl-substituted derivatives have been calculated using a non-iterative approximation to the coupled-perturbed Kohn-Sham equation where the first-order derivatives of the field-dependent Kohn-Sham matrix are estimated using the finite field method" . This approximation turns out to be reliable with differences with respect to the fully coupled-perturbed Kohn-Sham values smaller than 1% and 5% for a and p, respectively. The agreement with the MP2 results is also good, which enables to employ this simplified method to deduce structure-property relationships. 

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