1-(1-Naphthyl)isoquinoline

Ljungström, Evert; Lindqvist, Oliver; Overbeek, O.

doi:10.1107/s0567740878006512

Cited by 5 publications

(1 citation statement)

References 6 publications

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“…The hetaryl rings in the ground state are shifted off center and are stacked. Such ground-state deformations also appear in various crystal structures. − …”

Section: Discussionmentioning

confidence: 96%

Influence of the Position of an Annular Nitrogen Atom on the Magnitude of the Rotational Barriers in Atropisomers of 1,8-Dihetarylnaphthalenes

1997

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Five new atropisomerically chiral 1,8-dihetarylnaphthalenes were prepared by Pd(0)-catalyzed coupling reactions. Variable-temperature proton NMR spectra show those compounds with a 2'-pyridyl or 2'-pyrazinyl ring have a much lower energy barrier for rotation to interconvert conformational isomers than those with a 3'-pyridyl ring. Coalescence temperatures may differ by as much as 100 degrees C. The results of AM1 and PM3 computations indicate the preferred transition state for sigma-bond rotation places the annular nitrogen atom in the 2' or ortho position toward the face of the second hetaryl ring and not toward the naphthalene ring.

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“…The hetaryl rings in the ground state are shifted off center and are stacked. Such ground-state deformations also appear in various crystal structures. − …”

Section: Discussionmentioning

confidence: 96%

Influence of the Position of an Annular Nitrogen Atom on the Magnitude of the Rotational Barriers in Atropisomers of 1,8-Dihetarylnaphthalenes

1997

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Aromaticity as a Quantitative Concept. 3. Benzo‐fused five‐ and six‐membered heterocycles

et al. 1990

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A rather complete data set for 12 characteristics of 18 common benzo‐fused heterocycles yields two significant principal components. The loadings of the characteristics show a close correlation with those found for the same characteristics of monocyclic heterocycles. The scores for each bicycle are also closely related to those for the corresponding monocycle. The method demonstrates considerable predictive power.

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Condensation of 6-methyl-3-azapyrylium salts to pyrido[1,2-c]pyrimidinium derivatives

Shibaeva

Nechayuk

Borodaev

et al. 1991

Chem Heterocycl Compd

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1-(1-Naphthyl)isoquinoline

Cited by 5 publications

References 6 publications

Influence of the Position of an Annular Nitrogen Atom on the Magnitude of the Rotational Barriers in Atropisomers of 1,8-Dihetarylnaphthalenes

Influence of the Position of an Annular Nitrogen Atom on the Magnitude of the Rotational Barriers in Atropisomers of 1,8-Dihetarylnaphthalenes

Aromaticity as a Quantitative Concept. 3. Benzo‐fused five‐ and six‐membered heterocycles

Condensation of 6-methyl-3-azapyrylium salts to pyrido[1,2-c]pyrimidinium derivatives

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