Conformational equilibria of 3‐(cis‐styryl)phenanthrene and some benzologues
作者： J. B. M. Somers , W. H. Laarhoven
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摘要: An NMR investigation of cis and trans isomers styrylphenanthrene some benzologues was performed, in which Δtrans-cis values (δtrans-δcis), temperature dependence (ΔT) CS2 ASIS effects were determined. It concluded that the series styryl-phenanthrene (2),-benzo[c]-phenanthrene (1),-dibenzo[c,g]triphenylene (10),-hexahelicene (9) only 1 exists mainly as a cis-synrotamer, whereas other compounds cis-anti rotamer predominates varying degrees. The introduction an additional benzo group 2 at ring, containing styryl substituent, leads to styryl-chrysene (11) styryl-benzo[c]chrysene (12), shifts conformational equilibrium cis-syn rotamer. polar substituents para-position 2-styrylbenzo[c]phenanthrene has small influence on syn-anti equilibrium. observed are discussed.
sci-hub.se 参考文章(14)
W.H. Laarhoven And R.J.F. Nivard, Conformational studies on hexahelicenes—I: The NMR spectra of the benzohexahelicenes Tetrahedron. ,vol. 28, pp. 1803- 1810 ,(1972) , 10.1016/0040-4020(72)88059-1
M. H. de Jong, W. H. Laarhoven, Conformational preference of cis-1-aryl-2-(2-benzo[C]phenanthryl)-and cis-1-aryl-2-(3-phenanthryl)-ethenes Recueil des Travaux Chimiques des Pays-Bas. ,vol. 92, pp. 673- 682 ,(2010) , 10.1002/RECL.19730920615
W.H. Laarhoven, P.G.F. Boumans, Photodehydrocyclizations of stilbene-like compounds XIV Photosynthesis and photoreactions of 1,2- and 1,14-diphenylpentahelicene derivatives Recueil des Travaux Chimiques des Pays-Bas. ,vol. 94, pp. 114- 118 ,(2010) , 10.1002/RECL.19750940512
Fred Mulder, Gerard van Dijk, C. Huiszoon, Ab initio calculations of multipole moments, polarizabilities and long-range interaction coefficients for the azabenzene molecules Molecular Physics. ,vol. 38, pp. 577- 603 ,(1979) , 10.1080/00268977900101901
Wim H. Laarhoven, Theo J. H. M. Cuppen, Chiral solvent-induced asymmetric synthesis. Part 2. Photosynthesis of optically enriched hexahelicenes Journal of The Chemical Society-perkin Transactions 1. ,vol. 8, pp. 315- 318 ,(1978) , 10.1039/P29780000315
T. Ledaal, Solvent Effects in NMR Spectroscopy. The Geometry of Solute/Solvent Collision Complexes Tetrahedron Letters. ,vol. 9, pp. 1683- 1688 ,(1968) , 10.1016/S0040-4039(01)99029-X
Peter H. G. op het Veld, Wim H. Laarhoven, Intramolecular photocyclizations of o,o′-bis-(2-arylvinyl)biphenyls J. Chem. Soc., Perkin Trans. 2. ,vol. 8, pp. 268- 273 ,(1977) , 10.1039/P29770000268
Aksel A. Bothner‐By, Richard E. Glick, Medium Effects in the Nuclear Magnetic Resonance Spectra of Liquids. III. Aromatics The Journal of Chemical Physics. ,vol. 26, pp. 1651- 1654 ,(1957) , 10.1063/1.1743599
A. H. A. Tinnemans, W. H. Laarhoven, S. Sharafi-Ozeri, K. A. Muszkat, Photodehydrocyclizations of stilbene‐like compounds XV: Electronic overlap population as a reactivity measure in photocyclizations of pentahelicenes Recueil des Travaux Chimiques des Pays-Bas. ,vol. 94, pp. 239- 243 ,(2010) , 10.1002/RECL.19750941105
T. Schaefer, W. G. Schneider, On the Nature of Solvent Effects in the Proton Resonance Spectra of Unsaturated Ring Compounds. I. Substituted Benzenes Journal of Chemical Physics. ,vol. 32, pp. 1218- 1222 ,(1960) , 10.1063/1.1730877