Magnetochemische Untersuchungen organischer Stoffe. Über eine neue Methode zur Bestimmung von Dissoziationsgraden hexaarylsubstituierter Äthane

Müller, Eugen; Müller‐Rodloff, Ilse

doi:10.1002/jlac.19365210106

Cited by 21 publications

(2 citation statements)

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“…For the first time, a quantification of the instability of dimeric "triphenylmethyl" was given. This value was later confirmed by Müller [47] and much later with the correct structural assignment by Neumann. [48] In 1930, experimental rates of the oxidation of "triphenylmethyl" revealed the existence of a second reaction pathway, which leads to "the oil": The scavenging of oxygen by the radical and, and this was new, the direct oxidation of triphenylmethyl.…”

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confidence: 56%

Computational Chemistry as a Conceptual Game Changer: Understanding the Role of London Dispersion in Hexaphenylethane Derivatives (Gomberg Systems)

Rösel

Schreiner

2022

Israel Journal of Chemistry

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The present personal perspective sheds light on the checkered history of hexaphenylethane (HPE) and some of its key derivatives, including successes and failures in interpreting experimental as well as computational data. HPE has become a testing ground for chemical theory since the groundbreaking work of Gomberg in 1900. It sparked the growth of theoretical carbon chemistry beyond tetravalency, forced chemists to improve theory of color and chemical bonding by mesomeric resonance, and challenged the purely repulsive view on substituent effects. Understanding the origin of the instability of HPE on the one hand and the stability of the sterically much more crowded all-meta t Busubstituted HPE on the other hand may well be considered an important turning point in the appreciation of London dispersion (LD) and the analytical power of computational chemistry.

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confidence: 56%

Computational Chemistry as a Conceptual Game Changer: Understanding the Role of London Dispersion in Hexaphenylethane Derivatives (Gomberg Systems)

Rösel

Schreiner

2022

Israel Journal of Chemistry

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“…Alkali metal ions and tris-arylcarbanions are extensively paired in diethyl ether solution,l2 but the corresponding carbonium ions in formic acid solution appear to be essentially free, and a more quantitative, though indirect, comparison may be made between the theoretical energy difference ~E c , and the solvation energy AGs of the carbonium ion, on the one hand, and, on the other, the differential between the free energy AGE of ionization of the tris-arylcarbinols in formic acid, and the free energy AGE of dissociation of the hexa-arylethanes to the corresponding radicals in benzene solution,l6~ 17 Ar 3C-C Ar 3+ 2 Ar 3Ce.…”

Section: Fig 2-the Relations Between the Hiickel Delocalization Energ...mentioning

confidence: 99%

Ionic equilibria of tris-arylmethyl systems

Grinter¹,

Mason²

1964

Trans. Faraday Soc.

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The constants governing the equilibrium between the carbonium ions (I), (11) and (111), R = Hand p-or m-phenyl-, and the corresponding carbinols have been measured in formic acid solution at 20", and values of the appropriate acidity function HR have been derived for this medium containing added sodium formate or sulphuric acid. The relative stabilities of the tris-arylcarbonium ions are shown to be dependent upon, not only their n-electron delocalization energies, but also their solvation energies. The factors governing other tris-arylmethyl equilibria are discussed.The tris-arylmethyl chlorides dissociate in liquid sulphur dioxide,z or in chloroor nitro-hydrocarbons,2 to give the corresponding ion-pair and the free chloride and tris-arylcarbonium ion, ktz kb Ar,CCl+(Ar,C+Cl-)+Ar,C+ + Ci-. (1) Conductivity measurements give, for the sulphur dioxide solutions,l the dissociation constant Kexpt where [Ar,C+] [Cl-] -K b K e x p t = [Ar,CCI] + [(Ar,C+Cl-)]and values of the corresponding free energy of dissociation ( AGexpt = -RT in Kexpt)

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Der Magnetismus, ein modernes Hilfsmittel des organischen Chemikers

Müller

1938

Angewandte Chemie

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D o z e n t dev o v g a n i s c h e n A b t . d e s C h e r n i s c h e n I n s t i f 2 t t s d e r U n i v e r s i l a t J e n aLingeg. 1. Juli I938 n dieser Zeitschrift ist in den letzten Jahren schon mehr-Angeurandte Ckuinir 51.Jahrg.1938. 9 r . 3 8 Angewandle Ckemie 51.Jahrg.1938. Nr.38 ~ ~~ Z4) Sugden fand fur das Benzophenonkalium 70% Radikalgehalt, J . chem. SOC., London 1986, 440. E . Miilkr u. I . MulEer-RodZo//, Liebigs Ann. Chem. 631, 81 [1935]: vgl. auch R. Kwhn, H . Katz 11. W . Franke, Naturwiss. 22, 808 [1934]. 8 6 ) E . M t i l l~ u. I . Muller-Rodloff,ebenda 617, 134 119351 ;

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Magnetochemische Untersuchungen organischer Stoffe. Über eine neue Methode zur Bestimmung von Dissoziationsgraden hexaarylsubstituierter Äthane

Cited by 21 publications

References 3 publications

Computational Chemistry as a Conceptual Game Changer: Understanding the Role of London Dispersion in Hexaphenylethane Derivatives (Gomberg Systems)

Computational Chemistry as a Conceptual Game Changer: Understanding the Role of London Dispersion in Hexaphenylethane Derivatives (Gomberg Systems)

Ionic equilibria of tris-arylmethyl systems

Der Magnetismus, ein modernes Hilfsmittel des organischen Chemikers

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