Biphenyls effect

Thuvander, A., and Carlstein, M., Sublethal exposure or rainbow trout, Oncorhynchus mykiss, to polychlorinated biphenyls effects on the humoral immune response to Vibrio anguillarum, Fish Shellfish Immunol., 1, 77, 1991. 

Traas, T.P., Luttik, R., Klepper, O., Beurskens, J.E., Smit, M.D., Leonards, P.E.G., Hattum, B. van and Aldenberg, T. (2001). Congener-specific model for polychlorinated biphenyl effects on otter Lutra lutra) and associated sediment... 

Fein GG, Jacobson JL, Jacobson SW, et al. 1984b. Prenatal exposure to polychlorinated biphenyls Effects on birth size and gestational age. J Pediatr 105 315-320. 

Fig. 8.2-15 NaCl/H20 and naphthaline/biphenyl effective distribution coefficient...

The first three of a series of papers by Ridd and co-workers on Inductive and Field effects in Aromatic Substitution have appeared. Results of studies of the nitration of 4-phenylp5nidine and of 4-benzylpyridine in aqueous sulphuric acid were reported and use of the usual criteria (para 8.2) showed that in each case the conjugate acid was the species undergoing nitration. The values of where fm refers to the corresponding homocyclic compound (biphenyl or diphenylmethane) when plotted against r, the distance between the... 

Many chemical compounds have been described in the Hterature as fluorescent, and since the 1950s intensive research has yielded many fluorescent compounds that provide a suitable whitening effect however, only a small number of these compounds have found practical uses. Collectively these materials are aromatic or heterocycHc compounds many of them contain condensed ring systems. An important feature of these compounds is the presence of an unintermpted chain of conjugated double bonds, the number of which is dependent on substituents as well as the planarity of the fluorescent part of the molecule. Almost all of these compounds ate derivatives of stilbene [588-59-0] or 4,4 -diaminostilbene biphenyl 5-membeted heterocycles such as triazoles, oxazoles, imidazoles, etc or 6-membeted heterocycles, eg, coumarins, naphthaUmide, t-triazine, etc. 

Common examples of compounds that are amenable to carbon adsorption are aromatics (benzene, toluene) and chlorinated organics (trichloroethylene, trichloroethane [71-55-6, 75 -(9(9-j5y, tetrachloroethylene, polychlorinated biphenyls (PCBs), DDT /T(9-77-77, pentachlorophenol [87-86-5J. Compounds that are not adsorbed effectively by carbon include ethanol [64-17-5], diethylene glycol [111-46-6], and numerous amines (butylamine [109-73-9, 13952-84-6, 75-64-9], triethanolamine [102-71-6], cyclohexylamine [108-91-8], hexamethylenediamine [108-91-8] (1). Wastewater concentrations that are suitable for carbon adsorption are generally less than 5000 mg/L. 

It is known that the brain is one of the most sensitive sites of action of steroids in utero, and recently there have been suggestions that EDs may affect normal brain development and behaviour. For example, it has been alleged that in utero exposure to polychlorinated biphenyl compounds (PCBs) resulted in adverse effects on neurologic and intellectual function (memory and attention) in young children born to women who had eaten PCB contaminated fish in the USA." It has also been speculated that exposure to environmental pollutants with steroidal activity may be infinencing human sexual development and sexually controlled behavioiir." ... 

TCDD is the most potent inducer of chloracne. This has been well known since the accident in Seveso, Italy, in 1976 in which large amounts of TCDD were distributed in the environment subsequent to an explosion in a factory that produced a chlorophenoxy herbicide, 2,4,5-T. TCDD is an impurity produced during the production of 2,4,5-T. The most common long-term effect of TCDD exposure was chloracne. Exposed individuals also suffered increased excretion of porphyrins, hyper-pigmentation, central nervous system effects, and liver damage and increased risk of cancer was a long-term consequence of the exposure. In addition to TCDD, polychlorinated biphenyls (PCBs), polychlorinated dibenzofurans, and polychloronaphthalens cause chloracne as well as other effects typical of TCDD. 7i... 

Dioxins are prominent members of the class of polychlorinated hydrocarbons that also includes diben-zofuran, biphenyls and others. Dioxins are highly toxic environmental contaminants. Like others small planar xenobiotics, some dioxins bind with high affinity to the arylhydrocarbon (Ah) receptor. Dioxins activate the receptor over a long time period, but are themselves poor substrates for the enzymes which are induced via the Ah-receptor. These properties of the dioxins and related xenobiotics may be important for the toxicity of these compounds. Dioxins like 2,3,7,8-tetrachloro-p-dibenzodioxin can cause persistent dermatosis, like chloracne and may have other neurotoxic, immunotoxic and carcinogenic effects. 

At 0.9 °C the rate of bromination of biphenyl relative to benzene was approximately 1,270, compared to 26.9 in the presence of mineral acid, and this latter value is fairly close to that obtained with 50 % aqueous dioxan. The possibility that the positive brominating species might be protonated bromine acetate, AcOHBr+, was considered a likely one since the reaction rate is faster in aqueous acetic acid than in water, but this latter effect might be an environmental one since bromination by acidified hypobromous acid is slower in 50 % aqueous dioxan than in... 

De la Mare et al.260 measured the rates of chlorination of biphenyl, a wide range of its methyl derivatives, and anisole in acetic acid at 25 °C. Second-order rate coefficients (104 2) were biphenyl (6.40), 2-methylbiphenyl (3.20), 3-methyl-biphenyl (820), 4-methylbiphenyl (30.0), 2.2 -dimethylbiphenyl (4.40), 3.3 -dimethylbiphenyl (2,630), 4,4 -dimethylbiphenyl (70.0), 2,6 -dimethylbiphenyl (1,130), 3,4,3, 4 -tetramethylbiphenyl (19,300), anisole (12.5 x 104), and these results showed very clearly the effect of steric inhibition of resonance between the phenyl rings through the presence of ortho methyl groups260. Similar (but rather more emphatic) results were obtained262 in chlorination of the /-butyl derivatives for which the corresponding rate coefficients were 2-/-butylbiphenyl (1.0) 4-/-butylbiphenyl (25.7), 2,2 -di-/-butylbiphenyl (1.8), 4,4 -di-/-butylbiphenyl (70.0). 

The rates of chlorination of bridged biphenyls have also been measured and show the effect of coplanarity on reactivity. Second-order rate coefficients (104A 2) at 25 °C were fluorene (1,700), 9,10-dihydrophenanthrene (170), 1,2 3,4-di-benzocyclohepta-1,3-diene (9.70), 5-methyl-l,2 3,4-dibenzocyclohepta-l,3-diene... 

Gore et al.426 have used chloroform as a solvent for acetylation catalysed by aluminium chloride and at 45-55 °C find that a 2-methoxy substituent in naphthalene increases the reactivity of the 1 position 1.72 times, of the 6 position 3.8 times, and of the 8 position, 0.9 times the former and latter of these results indicate a considerable steric effect. Likewise, a 2-bromo substituent caused the reactivity of the 6 and 8 positions to be 0.63 and 0.58 times that of the corresponding positions in the unsubstituted compound. At 20-25 °C the relative reactivities of some polycyclics were as follows427 1-naphthyl, 1.0 3-phenanthryl 0.64 9-phenanthryl, 0.02 1-phenanthryl, 0.29 2-naphthyl, 0.28 2-phenanthryl, 0.12 4-phenanthryl, 0.0085. Some of these results seem to be due to steric hindrance, and the large difference in reactivity of naphthalene and biphenyl seems erroneous. 

---