Nitro-aromatic compounds relationships

Structure-Activity Relationships in Nitro-Aromatic Compounds... 

Table 10.1 Compilation of representative Quantitative Structure-Activity Relationships (QSAR) models for nitro-aromatic compounds...

Abraham, in collaboration with Taft, Kamlet, and Abboud, has made an interesting attempt to characterize the nature of a solvent in terms of its H-bond donor ability (HBD or), H-bond acceptor ability (HBA jS), and its specific dipolarity/polarizabiUty (jt ). He has used these parameters in multiparameter relationships to analyze medium effects on a variety of chemical processes. Briefly, the HBD propensities (a) were obtained from the enhanced sol-vatochromism of the t(30) probe relative to 4-nitroanisole, the HBA propensities (j8) from the enhanced solvatochromism of 4-nitroaniline relative to N,N-diethyl-4-nitroaniline in HBA solvents, and the rt values from solvent effects on the n n transition of nitro-substituted aromatic compounds. For a more detailed discussion of these parameters and their apphcations, the reader is referred to the original literature. ... 

Quite recently, the same research group compared the electrophilicity of 6-nitro-tetrazolo[l,5- ]pyridine and 6,8-dini-trotetrazolo[l,5- ]pyridine 11 with a series of electron-deficient aromatic and heteroaromatic compounds <2005JOC6242>. As reference nucleophiles, fV-methylpyrrole, indole, fV-methylindole, and some morpholino enamines were used. The reactivity of the electrophiles studied followed the linear-free energy relationship defined by Mayr et al. <2003ACR66>. 

Dopp, D. Reactions of Aromatic Nitro Compounds via Excited Triplet States. 55, 49-85 (1975) Dougherty, R. C. The Relationship Between Mass Spectrometric, Thermolytic and Photolytic Reactivity. 45, 93-138 (1974). 

The explosive properties of mixtures with ammonium nitrate depend on the quantitative relationship between the oxidizing agent and the explosive or combustible substance. According to Parisot and Laffitte s [9, 47] investigations the explosive properties of mixtures of aromatic nitro compounds with ammonium nitrate vary with the change in composition of the system in an almost rectilinear manner. The graph in Fig. 69 shows how the rate of detonation depends on the composition of mixtures of tetryl or picric acid with ammonium nitrate. T. Urbanski et al. [48] also obtained a rectilinear relationship for nitrostarch mixtures with ammonium or sodium nitrate (Fig. 71, p. 265). 

Debnath, A.K., Hansch, C. (1992) Structure-activity relationship of genotoxic polycyclic aromatic nitro compounds. Further evidence for the importance of hydrophobicity and molecular orbital energies in genetic toxicity. Environ. Mol. Mutagen. 20, 140-144. 

A.K. Debnath et al., Quantitative structure-activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test 2 Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella typhimurium TA100. Environ. Mol. Mutagen. 19, 53-70 (1992)... 

A.K. Debnath et al., Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34, 786-797 (1991)... 

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