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Benzo[1,2‐ h :4,3‐ h ′]diquinoline (“1,14‐Diaza[5]helicene”): Synthesis, Structure, and Properties

1989; Wiley; Volume: 28; Issue: 1 Linguagem: Inglês

10.1002/anie.198900861

1521-3773

Heinz A. Staab, Michael A. Zirnstein, Claus Krieger,

Molecular spectroscopy and chirality

Angewandte Chemie International Edition in EnglishVolume 28, Issue 1 p. 86-88 Communication Benzo[1,2-h:4,3-h′]diquinoline (“1,14-Diaza[5]helicene”): Synthesis, Structure, and Properties† Prof. Dr. Heinz A. Staab, Corresponding Author Prof. Dr. Heinz A. Staab Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this authorDipl.-Chem. Michael A. Zirnstein, Dipl.-Chem. Michael A. Zirnstein Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this authorClaus Krieger, Claus Krieger Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this author Prof. Dr. Heinz A. Staab, Corresponding Author Prof. Dr. Heinz A. Staab Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this authorDipl.-Chem. Michael A. Zirnstein, Dipl.-Chem. Michael A. Zirnstein Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this authorClaus Krieger, Claus Krieger Abteilung Organische Chemie, Max-Planck-Institut für medizinische Forschung, Jahnstrasse 29, D-6900 Heidelberg (FRG)Search for more papers by this author First published: January 1989 https://doi.org/10.1002/anie.198900861Citations: 57 † New “Proton Sponges”, Part 9.—Part 8: [3]. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical 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. References 1 Review on “Proton Sponges”: H. A. Staab, T. Saupe, Angew. Chem. 100 (1988) 895; Angew. Chem. Int. Ed. Engl. 27 (1988) 865. 2 M. A. Zirnstein, H. A. Staab, Angew. Chem. 99 (1987) 460; Angew. Chem. Int. Ed. Engl. 26 (1987) 460. 3 C. Krieger, M. A. Zirnstein, I. Newsom, H. A. Staab, Angew. Chem. 101 (1989); Angew. Chem. Int. Ed. Engl. 28 (1989) 84 4 R. W. Alder, M. R. Bryce, N. C. Goode, N. Miller, J. Owes, J. Chem. Soc. Perkin Trans. 1 1981, 2840; the name “Proton Sponge” was introduced by Aldrich Chemicals Co., Milwaukee, as the commercial name of this compound. 5 T. Saupe, C. Krieger, H. A. Staab, Angew. Chem. 98 (1986) 460; Angew. Chem. Int. Ed. Engl. 25 (1986) 451; for the X-ray structure analysis see [1]. 6 C. Y. Meyers, A. M. Malte, W. S. Matthews, J. Am. Chem. Soc. 91 (1969) 7510; C. Y. Meyers, W. S. Matthews, G. J. McCollum, J. C. Branca, Tetrahedron Lett. 1974, 1105. 7 Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Energie, Physik, Mathematik GmbH, D 7514 Eggenstein-Leopoldshafen 2 (FRG), on quoting the depository number CSD-53274, the names of the authors, and the journal citation. 8 R. Kuroda, J. Chem. Soc. Perkin Trans. 2 1982, 789; cf. also A. O. McIntosh, J. M. Robertson, V. Vand, J. Chem. Soc. 1954, 1661. Citing Literature Volume28, Issue1January 1989Pages 86-88 ReferencesRelatedInformation