Dinitrophenol structure

In this chapter, the voltammetric study of local anesthetics (procaine and related compounds) [14—16], antihistamines (doxylamine and related compounds) [17,22], and uncouplers (2,4-dinitrophenol and related compounds) [18] at nitrobenzene (NB]Uwater (W) and 1,2-dichloroethane (DCE)-water (W) interfaces is discussed. Potential step voltammetry (chronoamperometry) or normal pulse voltammetry (NPV) and potential sweep voltammetry or cyclic voltammetry (CV) have been employed. Theoretical equations of the half-wave potential vs. pH diagram are derived and applied to interpret the midpoint potential or half-wave potential vs. pH plots to evaluate physicochemical properties, including the partition coefficients and dissociation constants of the drugs. Voltammetric study of the kinetics of protonation of base (procaine) in aqueous solution is also discussed. Finally, application to structure-activity relationship and mode of action study will be discussed briefly. 

The constants of ion pair formation of 33 amines with 2,4-dinitrophenol in benzene (Ab) have been compared with the pAa in water56. The effects of structural variations on basicity are larger in water than in benzene for primary and secondary cyclic amines, but similar for tertiary amines. The Taft and Hancock equation [where <7 has the usual meaning and E° (R ) is the steric effect of a component substituent]... 

Ortho eliminations find widespread application in the structure elucidation of aromatic nitro compounds, e.g., nitroanilines, [200] dinitrophenols, [213] trini-troaromatic explosives, [214] and nitrophenyl-methanesulfonamides. [199] (Scheme 6.75 reproduced from Ref. [199] with permission. IM Publications 1997) ... 

Fig. 12 Proposed structure of (salen)CoX complex, where X = 2,4-dinitrophenolate and the salen ligand contains the sterically unencumbering methyl substituents...

Polysulfide Melt. Cl Sulfur Black 1 [1326-82-5] (Cl 53185), derived from 2,4-dinitrophenol, is the most important dye in this group which also includes the indophenol-type intermediates. The latter are applied in the stable leuco form. The derived dyes are usually confined to violet, blue, and green shades. Other members of this group are intermediates capable of forming quinoneimine (10) or phenazone structures (11) that produce red-brown or... 

Structures of two uncouplers of oxidative phosphorylation, 2,4-dinitrophenol (DNP) and carbonylcyanide-p-trifluoromethoxyphenylhydrazone (FCCP). DNP has a weakly dissociable proton on the oxygen atom FCCP has a similar proton on one of the nitrogens. 

The action of nitric acid on diacetylated p-aminophenol yields a dinitro derivative for which four structures are possible. Hydrolysis followed by deamination gives the known 3,5-dinitrophenol, thus proving that substitution occurs ortho to the acylated amino group.141... 

Finally Hubner and W. Schneider [21] defined the conditions under which the formation of the two isomeric dinitrophenols must proceed and pointed out the difference in their structures. They proved the p- nitrophenol was nitrated to 2,4-dinitrophenol when using 54% nitric acid, o- Nitrophenol is slightly more difficult to nitrate and yields a mixture of 2,6- and 2,4-dinitrophenols. The two isomers may be separated by steam distillation, since the 2,4- is more volatile than the... 

No reliable animal studies have demonstrated that DNOC causes cataracts in mammals. However, case reports of the coincidental occurrence of cataracts after ingestion of DNOC and the structural similarity between dinitrophenol and DNOC, both of which are uncouplers of oxidative phosphorylation, suggest that this effect may occur in humans exposed to DNOC. 

Ethyl dinitrophenols. Beil (Ref 1) lists only one compd of undetermined structure, with an expl Pb salt. Prepd by nitrating o-ethylphen-ol with cold fuming HN03 Refs l)Beil 6. 471 2)W.Suida S.Plohn, Monatsh 1, 181 (1880)... 

Molecularly Related Nitrophenols. To define more explicitly the relative influences of molecular structure and hydrophobic character upon rate of adsorption of pesticide materials by porous carbon, a number of pure dinitrophenols molecularly related to DNOSBP and DNOCHP have been studied. The molecular structures of DNOSBP, DNOCHP and the molecularly related dinitrophenols—DNP, DNC, DNT, and DNPCHP —are illustrated in Figure 5. 

Representative Chemicals Dinitrophenol (DNP) occurs in six different isomers - 2,3-DNP, 2,4-DNP, 2,5-DNP, 2,6-DNP, 3,4-DNP, and 3,5-DNP Synonyms A number of substituted 2,4-DNPs are sold under different trade names analogs include DNOC, 2,4-Dinitro-6-methylphenol Binapacryl, 2-s-Butyl-4,6-dinitrophenol-3-methylcrotonate Dinocap, 2,4-Dinitro-6-(l-methy- -heptyl)-phenyl-crotonate Dinoseb, 2,4-Dinitro-6-s-butylphenol Chemical Structure ... 

Dinitrophenols are used as fungicides, herbicides, or insecticides. The fungicidal, herbicidal, or insecticidal properties depend on minor differences in the chemical structures of the different dinitrophenol compounds. Several dinitrophenol compounds have more than one pesticidal use. The pesticidal use of one dinitrophenol, dinoseb, was eliminated in the United States in 1986. There has recently been a voluntary cancellation of all US product registrations for the fungicide/miticide Dinocap. 

With the aid of decoupling experiments and the INDOR technique, it was possible to define completely the structure and stereochemistry of erythristemine (1) with the exception of the configuration at C-11." In order to obtain the latter information, recourse was taken to A-ray analysis on the 2-bromo-4,6-dinitrophenolate salt of (1). This constitutes a new method and may be applicable elsewhere. Details of the structural and stereochemical elucidation of the interesting insecticidal alkaloid (2), which may be regarded as a ring-D degraded erythroidine structure, have appeared. ... 

Dinocap is an ester that is taken up by fungal spores or mites. It is hydrolyzed to the active phenol. It has low toxicity to plants and mammals. Dinocap is a mixture of several dinitrophenol esters, and the structure of one is shown. 

Researches have investigated the biological action of other alkyl-dinitrophenols as a function of the structure of the compounds (Byrde et al., 1969 Clifford et ai, 1969 and 1972). 

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