By E. Clar (auth.)
Polycyclic hydrocarbons are of curiosity in lots of fields of technology: theoretical chemistry, actual chemistry, natural chemistry, dyestuff chemistry and biology. in regards to the latter, i'm indebted to Dr. Regina Schoental of the scientific learn Council for the evaluate during this current paintings of carcinogenesis by way of polycyclic hydrocarbons. This e-book is designed to provide the proof in an easy and transparent order and to derive empirical ideas from them, however it doesn't current a com prehensive thought approximately polycyclic hydrocarbons. An try is made as an alternative to increase classical symbolism into smooth structural chemistry. hence wide use is made from Robinson's fragrant sextet, that's utilized in an uncompromising and strict means. This quasi-classical test is inspired additional via such thoroughly unforeseen dis coveries as these of Dewar benzene and of the digital asymmetry of officially symmetric hydrocarbons. How tough it's to damage clear of any validated frame of mind has been admirably expressed via Kekule ("Organische Chemie", 1861, half 1, web page four, translated from the German): "All our principles are dependent, to an quantity a lot more than we mostly think, on these of our predecessors. Our collected adventure, the notions of which our education has accustomed us to, of no matter what style they've been, impact the process our techniques way over we're keen to confess; in basic terms too often the next of our usually used, good trodden state of mind leads us to miss the best of correlations.
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Extra info for Polycyclic Hydrocarbons: Volume 1
Soc. A144, 166; A146, 223 (1934). 2. , "The Nature of the Chemical Bond", p. 137, Cornell University Press (1960). 3. Dewar, M. J. S. and Schmeising, H. , Tetmhedron 11, 96 (1960). 4. , Tetrahedron 9,202 (1960). 5. , Z. Phys. 70, 204 (1931); 76,628 and 638 (1932); Z. Elektrochem. 43,752 (1937); 61,867 (1957). 6. Pauling, L. , J. chern. Phys. 1, 678 (1933); Schomaker, V. , J. Amer. chem. Soc. , "The Nature of the Chemical Bond", p. 290, Cornell University Press (1960). 7. , Bastiansen, O. and Traettberg, Acta chem.
J. chern. Phys. 2, 488 (1934). CHAPTER 5 The Significance of Double Bonds and Kekule Structures for the Stability of Aromatic Systems Eine einmal festgestellte Tatsache kann nie Gegenstand des Streites sein ... Betrachtungen dagegen k6nnen, von denselben Tatsachen als Grundlage ausgehend, je nachdem man del' einen odeI' del' anderen vorwiegend Wert beilegt, zu ganz verschiedenen Ansichten fUhren. Durch Erkenntnis und Beriicksichtigung neuer Tatsachen miissen diese Ansichten del' Natur der Sache nach fortwahrend Veranderungen erleiden.
12-Dibenzozethrene (XIV) was also prepared and shows a typical aromatic spectrum. 9-dibenzoperylene (XVII). Bond fixation has obviously no influence on the aromatic character of the absorption spectra and the reactivity. 6 (I Iv ~"" ('(' l(') I (XV) A drastic comparison between a hydrocarbon with no Keku16 structure and an isomeric hydrocarbon with two fixed double bonds is provided by the dehydrogenation of the two hydro-derivatives (XVIII) and (XIX). ~o~~O ~) ~'t 0 I 1 (XX) I~I (XXI) Compound (XVIII) does not react with chloranil as dehydrogenating agent in boiling benzene.