Benzophenanthren

Benzophenanthrene [195-19-7] M 228.3, m 68°. Crystd from EtOH, pet ether, or EtOH/Me2CO. 

Naphthalene, acenaphthane, acenaphthene, fluorene, phenan-threne, anthracene, fluoranthene, pyrene, benzanthracene, benzophenanthrene, and benzpyrene... 

The aromatic compound, 9,10-benzophenanthrene, L, gives two complexes with the constitution Hg2(AsF5)2L3 and [Hg2(AsF5)2l2L. 

Benzotrifluoride, t311 Benzoylamide, b4 Benzoylbenzene, b53 Benzoyl peroxide, d69 1,2-Benzophenanthrene, b6... 

Synonyms AI3-50599 BA B(a)A Benzanthracene Benz[ ]anthracene 1,2-Benzanthracene 1,2-Benz[a]anthracene 2,3-Benzanthracene Benzanthrene 1,2-Benzanthrene Benzoanthracene 1,2 Benzoanthracene Benzo[a]phenanthrene Benzo[6]phenanthrene 2,3-Benzophenanthrene CCRIS 69 EINECS 200-280-6 Naphthanthracene NSC 30970 RCRA waste number U018 ... 

Synonyms AI3-00867 Benz[a]phenanthrene Benzo[a]phenanthrene Benzo[a]phenanthrene 1,2-Benzophenanthrene 1,2-Benzphenanthrene BRN 1909297 1,2-Dibenzonaphthalene CCRIS 161 1,2,5,6-Dibenzonaphthalene EINECS 205-923-4 NSC 6175 RCRA waste number U050. 

Synonyms BA benzanthracene 1,2-benz(anthracene benzo([Pg.68]

Benzo[ghi]perylene (1,12-benzoperylene) [191-24-2] M 276.3, m 273 , 277-278.5 , 278-280 . Purified as light green crystals by recrystn from CgHg or xylene and sublimes at 320-340 and 0.05mm [UV HCA 42 2315 1959 B 65 846 1932 Fluoresc. Spectrum JCS 3875 1954], 1,3,5-Trinitrobenzene complex m 310-313° (deep red crystals from C Hg) picrate m 267-270° (dark red crystals from styphnate m 234° (wine red crystals from C6H6). It recrystallises from propan-l-ol [JCS 466 1959], 3,4-Benzophenanthrene [195-19-7] M 228.3, m 68 . Crystd from EtOH, pet ether, or EtOH/Me2CO. 

Dimercury(I) n complexes are formed between aromatic compounds and Hg2(AsF6)2 in liquid S02 as solvent.113,121 Insoluble complexes with the ratio arene Hg2+ = 1 1 (arene = benzene, naphthalene, 2-methylnaphthalene, 2,6-dimethylnaphthalene, acenaphthene, fluor-anthrene, phenanthrene, anthracene, 9,10-dimethylanthracene or 1,3-dinitrobenzene) or 1 2 (arene = 9,10-benzophenanthrene) have been characterized by elemental analysis and, in some cases, by Raman spectrometry.113,120 The 13CNMR data allow the estimation of formation constants for the hexamethylbenzene, p-xylene and 1,4-dichlorobenzene complexes together with the chemical shifts for the bound substrates in these cases.121 Probably the coordination compounds of dimercury(I) salts with carbazole, dibenzofuran and diben-zothiophene are also n complexes.122... 

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

Benzophenanthrene Benzyl bromide Benzyl chloride Benzyl ethyl sulfide Benzyl iodide Benzyl methyl ketone Benzyl methyl sulfide Bicyclo[4.1.0]heptane Bicyclo[3.1.0]hexane... 

Theoretical calculations on 3,4-benzophenanthrene (3) and tetrabenzo-naphthalene (4) indicate that the potential energy of deformation arising from out-of-plane bending and ring-angle distortion is of the same order, but that the combined effect of both is much smaller than either separately. 

Fig. 3. (a) Benzophenanthrene. (6) Dibenzofluorene. (c) Phenanthrene. (d) Fluorene. (e) Fluoranthene. In these hydrocarbons the interfering protons are shown black and their van der Waals radii are shown dotted (after Reid, 1957). 

The strong interaction found in benzophenanthrene (Fig. 3a) is considerably reduced by the change in angle introduced by the five-membered ring in dibenzofluorene (Fig. 3b). Corresponding reductions in frequency shifts are found in the phenanthrene-fluorene-fluoranthene series (Fig. 3c, d, e). Here the phenanthrene-like interaction is much reduced in fluorene and virtually removed in fluoranthene. 

It is not easy to put forward any plausible explanation for the pKa values of the other acids listed in Table 4, although the authors attempt this by considering the effect of ring warping which Herbstein and Schmidt demonstrated in 3,4-benzophenanthrene. 

Steric interactions of atoms in close proximity cause deformation of electronic configurations and may give rise to feeble dipole moments in certain polycyclic hydrocarbons. The observed moments in Debye units (Bergmann et al., 1951) are 0-45 + 0-15 D for perylene (5) and 0-70 + 0-07 D for 3,4-benzophenanthrene (3). Triphenylene (6) and tetrabenzonaphthalene (4) had no dipole moments. 

The dipole moments found in perylene and 3,4-benzophenanthrene can be explained by assuming that intramolecular overcrowding causes these molecules to be non-planar. The resulting differences in electronegativities of the various carbon atoms in the molecules could then quite easily be responsible for the weak but measurable dipole moments which were found. 

Class D. 3,4-Benzophenanthrene and skeletally similar molecules the following compounds are discussed ... 

D. 3,4-Benzophenanthrene, 2,13-benzofluoranthene, 1,12-dimethyl-3,4-benzophenanthrene, 1 -methyl-3,4-benzophenanthrene, tetra-benzonaphthalene, diphenylene naphthacene, diperinaph-thyleneanthracene, and dinaphthoperopyrene. 

Fig. 17. 3,4-Benzophenanthrene a perspective drawing given by Reid (1957) based on the results of Herbstein and Schmidt s analysis. The diagonals across which the benzene rings fold are shown dotted the circles represent the van der Waals radii for hydrogen.

In 3,4-benzophenanthrene, the two overcrowded carbon atoms Cx and C12 would be only 2-4 A apart in a regular planar model. This distance, while much less than the sum of the van der Waals radii, is considerably greater than a covalent bond distance. The effect of linking Cx and C12 by a covalent bond is to convert 3,4-benzophen-anthrene into 2,13-benzofluoranthene (82). The crystal structure of this... 

Evidence of intramolecular overcrowding in 3,4-benzophenanthrenes, obtained from the ultraviolet absorption studies, has been discussed by Johnson (1959). It was predicted that the methylene-bridged hydrocarbon, 1,12-methylenebenzophenanthrene (85), should afford the spectrum of a 1,12-dimethylbenzophenanthrene devoid of any steric interference induced by the overcrowded methyl groups. A comparison of the ultraviolet absorption spectra of 1,12-dimethylbenzophenanthrene (83), benzophenanthrene (3), 6,7-dimethylenebenzophenanthrene (84),... 

A more complex case of molecular overcrowding of the benzophenanthrene type is found in tetrabenzonaphthalene (86). The crystal structure of this molecule has been studied in its most favourable projection by Herbstein and Schmidt (1954b). The results of this partial analysis rule out a planar centrosymmetric structure and favour a molecule having 222 molecular symmetry with distortions of the benzene rings, as shown in (86), comparable to those found in 3,4-benzophenanthrene no molecular symmetry is required by the crystal. 

Dibenzophenanthrene is even more overcrowded than 3,4-benzophenanthrene in a planar undistorted molecule the distance... 

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