1954
DOI: 10.1039/jr9540003314
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The structure of overcrowded aromatic compounds. Part IV. The crystal structure of tetrabenzonaphthalene

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Cited by 13 publications
(5 citation statements)
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“…The four conformers A , A′ , P , and M can therefore be symbolically represented as (+, + ), (− – ), (+ – ), and (− + ), respectively (Figure e). Previous studies , has shown that the ground state of a free DBC molecule is the chiral conformer P or M , and the energy of the achiral conformer A ( A′ ) is much higher, which is confirmed by our calculations based on density functional theory (DFT). However, the energy diagram changes dramatically when the DBC molecules are deposited on Cu(111) surface, as indicated by our calculations (Supporting Information, Figure S1).…”
Section: Results and Discussionsupporting
confidence: 88%
See 1 more Smart Citation
“…The four conformers A , A′ , P , and M can therefore be symbolically represented as (+, + ), (− – ), (+ – ), and (− + ), respectively (Figure e). Previous studies , has shown that the ground state of a free DBC molecule is the chiral conformer P or M , and the energy of the achiral conformer A ( A′ ) is much higher, which is confirmed by our calculations based on density functional theory (DFT). However, the energy diagram changes dramatically when the DBC molecules are deposited on Cu(111) surface, as indicated by our calculations (Supporting Information, Figure S1).…”
Section: Results and Discussionsupporting
confidence: 88%
“…DBC, the conformation-switchable molecule we investigated in this study, is a helicene derivative with a double-helicene structure. It has long been known as a kind of overcrowded nonplanar polycyclic hydrocarbon and has been investigated as a typical chiral core for liquid crystal studies. The structural feature and the conformational changes of DBC molecules can be well understood under the framework of helicene’s notation, as illustrated in Figure . The chemical structure of DBC can be viewed as the combination of two chiral [4]­Helicene ([4H]) molecules with the center-overlapped naphthalene units.…”
Section: Results and Discussionmentioning
confidence: 99%
“…Such an almost perpendicular orientation of pertphenyl groups is also indicated by spectroscopic methods (281, 299). Among a number of other polycyclic aromatic hydrocarbons that can be considered as pen derivatives of naphthalene, crystal-structure studies have been reported on benzo [c jphenanthrene (255,265,274,276), 1,12-dimethylbenzo[cjphenanthrene (274)(275)(276), and tetrabenzonaphthalene (255,266). A summary of the crystal structure analysis of these overcrowded molecules is available elsewhere (521).…”
Section: IImentioning
confidence: 95%
“…Naphthalenes substituted by bulky groups in the peri positions are distorted from planarity" both octachloronaphthalene C10CI 8 and tetrabenznaphthalene C26H16 are molecules of this type. The available information [C10C18, isotropic refinement of visual intensities, R = 21% (Gafner & Herbstein, 1963); C26H16, X,Z coordinates only (Herbstein & Schmidt, 1954)] is inadequate and the structures have therefore been redetermined with intensities measured on a fourcircle diffractometer. The new coordinates are in remarkably good agreement with those determined by photographic methods.…”
Section: Introductionmentioning
confidence: 99%
“…Peri interactions in substituted naphthalenes have been reviewed by Balasubramaniyan (1966) and intramolecular overcrowding by Ferguson & Robertson (1963) and Avoyan, Struchkov & Dashevskii (1966). "1" Space group was P21/a according to Herbstein & Schmidt ( 1954). Reorientation matrix is (new axes, indices) = [ 101/010/00 i] x (old axes, indices).…”
Section: Introductionmentioning
confidence: 99%