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Benzo[1,2-h:4,3-h′]diquinoline (“1,14-Diaza[5]helicene”): synthesis, structure, and properties

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Zirnstein,  Michael A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Staab, H. A., Zirnstein, M. A., & Krieger, C. (1989). Benzo[1,2-h:4,3-h′]diquinoline (“1,14-Diaza[5]helicene”): synthesis, structure, and properties. Angewandte Chemie International Edition, 28(1), 86-88. doi:10.1002/anie.198900861.


Cite as: https://hdl.handle.net/21.11116/0000-000B-4A30-C
Abstract
Despite almost equal N ⃛N distances in 1 and 2 (272.8 and 270.5 pm) the basicity constant of 2 is almost two powers of ten smaller than that of 1. The reason for this could be the helical structure of 2, which almost removes the destabilizing “lone-pair” interaction of the N atoms in the case of the free base and hinders an N ⃛H ⃛N bridge along the preferred directions of the “lone pairs” of the N atoms in the case of 2a.