Ueber die Spaltung der Propyl‐benzyl‐phenyl‐methyl‐ammoniumbase in ihre optischen Antipoden

Wedekind, E.; Fröhlich, E.

doi:10.1002/cber.190503803172

Cited by 14 publications

(1 citation statement)

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“…Treatment of the di-Grignard reagent formed from 6a with BF 3 etherate gives the racemic borate as its magnesium bromide salt. This salt was resolved by addition of one enantiomer of 7 …”

Section: Resultsmentioning

confidence: 99%

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

1998

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An induced circular dichroism (CD) spectrum is observed for 1,1‘,3,3,3‘,3‘-hexamethyl-9-phenyl-indocarbocyanine, 1,1‘-diethyl-2,2‘-cyanine, 1,1‘-di-(3,5-di-tert-butyl)benzyl-2,2‘-cyanine, or 1,1‘-di-(4-tert-butyl)benzyl-2,2‘-cyanine when penetrated into a chiral cavity of either spirobi[(2-methyl)borataxanthene] or spirobi[(3-methyl)borataxanthene]. Within the ion pair, the cyanine dye exists in two (or more) interconverting conformations of unequal energy. Solid-state structural evidence suggests that a nitrogen-forward mode for penetration by the cyanine dominates the solution behavior. A critical feature for the observation of induced circular dichroism is that the dye is twisted in the ground state. The free energy difference between the diastereomers with right- and left-handed twist in the chiral cavity of the borate is less than 1 kcal/mol, but this is sufficient to induce the CD spectrum. The magnitude of the observed CD spectrum is dependent on the structure of both the cyanine and borate.

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“…Treatment of the di-Grignard reagent formed from 6a with BF 3 etherate gives the racemic borate as its magnesium bromide salt. This salt was resolved by addition of one enantiomer of 7 …”

Section: Resultsmentioning

confidence: 99%

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

1998

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Die Geschwindigkeit der Autoracemisation von optisch‐aktiven Ammoniumsalzen ¹).

Wedekind

1906

Zeitschrift für Elektrochemie und angewandte physikalische Chem

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Hepp¹

1906

Ber. Dtsch. Chem. Ges.

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diese iiur verschwindend aus dern Wisrnuthsalze und der angewendeten Papierurnbiillung heraustreten kann. Diea zeigte sich an einem Theile des die obige Curve liefernden Praparates, dem durch Eintaachen eines Kupferetreifena in die ealzsanre LiisuDg der Antheil, welcber die a-Strahlen liefert, eotzogen worden war. Das Wiemuthoxychlorid erlitt hierdurch keine merkliche Aenderung dee Abfalles der $-Strahlung.

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Ueber die Spaltung der Propyl‐benzyl‐phenyl‐methyl‐ammoniumbase in ihre optischen Antipoden

Cited by 14 publications

References 11 publications

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

Die Geschwindigkeit der Autoracemisation von optisch‐aktiven Ammoniumsalzen ¹).

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Ueber die Spaltung der Propyl‐benzyl‐phenyl‐methyl‐ammoniumbase in ihre optischen Antipoden

Cited by 14 publications

References 11 publications

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

Cyanine Borate Penetrated Ion Pair Structures in Solution and the Solid State: Induced Circular Dichroism

Die Geschwindigkeit der Autoracemisation von optisch‐aktiven Ammoniumsalzen 1).

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Die Geschwindigkeit der Autoracemisation von optisch‐aktiven Ammoniumsalzen ¹).