Abstract
The fine structure of 2-(indane-1′,3′-dionid-2′-yl)pyridinium (α-pyrophthalone) was determined by PMR spectroscopy and x-ray diffraction analysis. The α-pyrophthalone molecule is almost planar; the dihedral angle between the pyridine ring and the indanedione ring is 5°. The structure is stabilized by an intramolecular hydrogen bond with a length of 2.73 Å. The molecules are packed in the crystal at van der Waals distances similar to those in molecular self-complexes. The data obtained for α-pyrophthalone confirm a dipolar ion structure.
Similar content being viewed by others
Literature cited
O. Ya. Neiland, I. K. Raiskuma, V. É. Kampar, S. V. Kalinin', D. A. Krauze, G. G. Pukitis, A. N. Plate, and T. L. Andreeva, Summaries of Papers Presented at the Fourth All-Union Conference on the Chemistry of Dicarbonyl Compounds [in Russian], RPI, Riga (1976), p. 105.
G. D. Manly, A. Richardson, A. M. Stock, C. B. Tilford, and E. D. Amstutz, J. Org. Chem., 23, 373 (1958).
I. G. Lombardino, J. Org. Chem., 32, 373 (1958).
B. Manuikan, P. Niklaus, and H. Ehrsaen, Helv. Chim. Acta, 52, 1259 (1969).
L. G. S. Brooker and G. H. Keyes, J. Am. Chem. Soc., 23, 5356 (1951).
Ya. Ya. Katsen, O. Ya. Neiland, and Ya. Ya. Linaberg, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 5, 576 (1972).
R. Kuhn and F. Bär, Liebigs Ann. Chem., 316, 155 (1935).
I. Amiel, I. Ploquin, L. Sparfel, G. Le-Baut, and R. Floch, Bull. Soc. Chim. France, 9–10, 2154 (1974).
P. Grews, R. R, Kintner, and H. C. Padget, J. Org. Chem., 38, 4391 (1973).
G. Bravic, F. Brechtel, J. Gaultier, and C. Hauw, Cryst. Struct. Comm., 5, 1 (1976).
F. Brechtel, G. Bravic, J. Gaultier, and C. Hauw, Cryst. Struct. Comm., 1, 159 (1972).
G. Bravic, J. Gaultier, and C. Hauw, Cryst. Struct. Comm., 5, 5 (1976).
I. Gsöregh and R. Norrestam, Acta Cryst., B32, 2450 (1976).
B. Bak, L. Hansen, and J. Rastrup-Andersen, J. Chem. Phys., 22, 2013 (1954).
C. Rerat, Acta Cryst., 15, 427 (1962).
V. F. Kaminskii, R. P. Shibaeva, and O. Ya. Neiland, Zh. Strukt. Khim., 17, 898 (1976).
A. E. Shvets, Ya. Ya. Bleidelis, R. P. Shibaeva, and L. O. Atovnyan, Zh. Strukt. Khim., 13, 745 (1972).
A. E. Shvets, A. A. Kemme, Ya. Ya. Bleidelis, Ya. F. Freimanis, and R. P. Shibaeva, Zh. Strukt. Khim., 14, 576 (1973).
Ya. Ya. Bleidelis, A. E. Shvets, and Ya. F. Freimanis, Zh. Strukt. Khim., 17, 1096 (1976).
H. Huber, Ber., 36, 1653 (1903).
I. Ploquin, L. Sparfel, G. Le-Baut, and R. Floch, Compt. Rend., 279, 1150 (1974).
G. Germain, P. Main, and M. M. Woolfson, Acta Cryst., A27, 368 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1076–1080, August, 1978.
Rights and permissions
About this article
Cite this article
Kemme, A.A., Bundule, M.F., Bleidelis, Y.Y. et al. Chemical peculiarities and structure of 2-(indane-1′, 3′-dionid-2′-yl)pyridinium (α-pyrophthalone). Chem Heterocycl Compd 14, 865–869 (1978). https://doi.org/10.1007/BF00469864
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00469864