Phenanthrene benzo

Chrysene or Benzophenanthrene (called Chrysen or 1,2 - Benzo-phenanthren in Ger),... 

The authors explain this anomaly by pointing out that in benzo-phenanthrene itself the benzene rings are non-coplanar (Herbstein and Schmidt, 1954), and as a result the carboxyl group at position 1 could be approximately coplanar with the ring to which it is attached. This in turn would imply that the acid-weakening resonance effect becomes effective. This, together with the acid-weakening effect of steric hindrance to solvation, could account for the relative weakness of 1-benzophenanthroic acid. 

SYNS BENZO(a)PHENANTHRENE 1,2-BENZO-PHENANTHRENE BENZ(a)PHENANTHRENE 1,2-BENZPHENANTHRENE 1,2,5,6-DIBENZO-NAPHTHALENE RCRA WASTE NUiMBER U050... 

Laarhoven has examined the fate of the dihydrophenanthrene intermediate (148) formed by photocyclisation of the styryl benzo-phenanthrenes (149). When the reaction is performed in the presence of iodine as oxidant the expected arene (150) is obtained but in the absence of the oxidant compound (148) rearranges to the more stable, isolable dlhydroarenes (151) and (152). This rearrangement is base catalysed and the proportions of (151) and (152) isolated depend upon the nature of the base and the solvent. 

Figure 1.4 Two-dimensional plot of HPLC (log /J and GC (log Iq) retention indexes (1) naphthalene (2) 2-methylnaphthalene (3) 2,3-dimethylnaphthalene (4) 2,3,6-trimethyl-naphthalene (5) biphenyl (6) fluorene (7) dibenzothiophen (8) phenanthrene (9) 2-methylphenanthrene (10) 3,6-dimethylphenanthrene (11) benzo[a]fluorene (12) chrysene (data replotted from reference (31)).

Besides a parent ion, the mass spectra of benzo- and dibenzothiepins show the corresponding naphthalene or phenanthrene radical cations as the base peak.2-16 The mass spectra of 1-benzo-thiepin 1-oxides and 1,1-dioxides show the same naphthalene radical cation, formed by loss of sulfur monoxide or sulfur dioxide, respectively.14 In contrast, in the mass spectrum of 2,7-di-terf-butylthiepin peaks resulting from the loss of sulfur are not found.17... 

The series M(PP)C1 (PP = 2,ll-bis(diphenylphosphinomethyl)benzo[c]-phenanthrene M = Cu, Ag, Au) is interesting in showing group trends (Table 4.7) where the silver and copper complexes have trigonal coordination and the gold member is linear [50]. 

Figure 3 depicts profiles of Total PAH fluxes vs. time (36). The following polycyclic hydrocarbons have been determined by high performance liquid chromatography, variable wavelength absorption detection Naphthalene, acenaphthylene, 7,12-dimethylbenzanthracene, 2-methylnaphtalene, fluorene, acenaphtene, phenanthrene, 2,3-dimethylnaphtalene, anthracene, fluoranthene, 1-methylphenanthrene, pyrene, 2,3-benzofluorene, triphenylene, benz(a)anthracene, chrysene, benzo(b)fluoranthene, benzo(k)fluoranthene, perylene, benzo(e)pyrene, 1,2,3,4-dibenzanthracene, benzo(a)pyrene, and 1,2,5,6-dibenzanthracene. 

Turning to the acute toxicity of PAH, terrestrial organisms will be dealt with before considering aquatic organisms, to which somewhat different considerations apply. The acute toxicity of PAHs to mammals is relatively low. Naphthalene, for example, has a mean oral LD50 of 2700 mg/kg to the rat. Similar values have been found with other PAHs. LC50 values of 150 mg/kg and 170-210 mg/kg have been reported, for phenanthrene and fluorene, respectively, in the earthworm. The NOEL level for survival and reproduction in the earthworm was estimated to be 180 mg/ kg dry soil for benzo[a]pyrene, chrysene, and benzoMfluoranthene (Enviromnental Health Criteria 202). 

The photochemical transformation of phenanthrene sorbed on silica gel (Barbas et al. 1996) resulted in a variety of products including c -9,10-dihydrodihydroxyphenanthrene, phenanthrene-9,10-quinone, and a number of ring fission products including biphenyl-2,2 -dicarboxaldehyde, naphthalene-l,2-dicarboxylic acid, and benzo[c]coumarin. 

Note Bi, biphenyl Nap, naphthalene Phe, phenanthrene Anth, anthracene Hu, fluoranthene Pyr, pyrene Chr, chrysene BaAnth, benz[a]anthracene BaPyr, benzo[a]pyrene BbFlu, benzo[h]fluoranthene DBaAnth, dibenz[a,/i]anthracene 3-Me-Chol, 3-methylcholanthrene. 

The transformation of benzene, toluene, naphthalene, biphenyl, and benzo[a]pyrene to the corresponding phenols (Trower et al. 1989) by Streptomyces griseus, and of phenanthrene by Streptomyces flavovirens to ( )tran5 -[95, 105 ]-9,10-dihydrodihydroxyphenanthrene with minor amounts of 9-hydroxyphenanthrene (Sutherland et al. 1990). 

A cytochrome P450 has been purified from Saccharomyces cerevisiae that has benzo[a]pyrene hydroxylase activity (King et al. 1984), and metabolizes benzo[fl]pyrene to 3- and 9-hydroxybenzo[fl]pyrene and benzo[fl]pyrene-7,8-dihydrodiol (Wiseman and Woods 1979). The transformation of PAHs by Candida Upolytica produced predominantly monohydroxyl-ated products naphth-l-ol from naphthalene, 4-hydroxybiphenyl from biphenyl and 3- and 9-hydroxybenzo[fl]pyrene from benzo[fl]pyrene (Cerniglia and Crow 1981). The transformation of phenanthrene was demonstrated in a number of yeasts isolated from littoral sediments and of these, Trichosporumpenicillatum was the most active. In contrast, biotransformation of benz[fl]anthracene by Candida krusei and Rhodotorula minuta was much slower (MacGillivray and Shiaris 1993). 

Although a number of white-rot fungi have been examined and shown to degrade PAHs (Field et al. 1992), greatest attention has probably been directed to Phanerochaete chrysosporium and Pleurotus ostreatus, and to the PAHs anthracene, phenanthrene, pyrene, and benzo[a]pyrene that will be used to illustrate the cardinal principles. A substantial fraction of PAHs may also be sorbed to the biomass—40% for phenanthrene and 22% for benzo[a]pyrene (Barclay et al. 1995). The degree of mineralization of PAHs by white-rot fungi may sometimes be quite low, for example, for Pleurotus ostreatus, yields were 3.0, 0.44, 0.19, and 0.19% for phenanthrene, pyrene, fluorene, and benzo[a]pyrene, respectively (Bezalel et al. 1996a). 

BCR Analytical Approach for the Certification of PAHs in Natural Matrix CRMs Prior to the certification analyses for the CRM, each participating laboratory has to prepare standard solutions of the analytes to be determined from certified reference compounds (purity >99.0 %) to calibrate their instruments for response and response linearity (multiple point calibration), detection limit, and reproducibility. In the case of PAH measurements, reference compounds of certified purity are used as internal standards, which are not present at a detectable concentration in the matrix to be analyzed (e.g. indeno[i,2,3-cd]fluoranthene (CRM 267), 5-methylchrysene (CRM 081R), benzo[f ]chry-sene (CRM 046), picene (CRM 168), and/or phenanthrene-dio). 

Sander and wise have proposed a test method to determine the bonding chemistry used to prepare octadecylsiloxane column packings based on the relative retention of three polycyclic aromatic hydrocarbons, benzo[a]pyrene (BaP), phenanthro-phenanthrene (PhPh), and l,2 3,4 5,6 7,8-tetrabenzonaphthalene (TBN) eluted with the mobile phase acetonitrile-water (85 15) [52,67,199,210]. On monomeric phases the test solutes elute in the... 

Extension of -conjugation from naphthalene to anthracene and phenanthrene has a small effect on the tmax of the photomerocyanine form. Replacement of the indoline ring with piperidine, benzoxazole, or benzo-thiazole83 has resulted in hypsochromic shift by ca. 10 nm.72... 

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