Abstract
bis-Isonicotinoyl hydrazone of 2,5-diformylpyrrole existing in the crystal in the form of a tetrahydrate of the hydrazone tautomeric form is synthesized and its structure is described. In the crystal, an infinite three-dimensional network of hydrogen bonds is formed by hydrazone molecules. The neighboring hydrazone molecules are bonded by intermolecular π stacking interactions. A quantum chemical calculation of the geometry and total energy of possible tautomers in vacuum and an aqueous solution is performed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. D. Popov, A. N. Morozov, I. N. Shcherbakov, et al., Russ. Chem. Rev., 78, No. 7, 642 (2009).
A. M. Stadler and J. Harrowfield, Inorg. Chim Acta, 362, No. 12, 4298 (2009).
S. N. Pandeya and J. R. Dimmock, Pharmazie, 48, No. 9, 659 (1993).
S. Rollas and Ş. G. Küçükgüzel, Molecules, 12. No. 8, 1910 (2007).
V. A. Kogan, S. I. Levchenkov, L. D. Popov, and I. N. Shcherbakov, Russ. J. Gen. Chem., 79, No. 1, 2767 (2009).
S. Ianelli, M. Nardelli, and C. Pelizzi, Gazz. Chim. Ital., 115, 375 (1985).
R. Alonso, E. Bermejo, R. Carballo, et al., J. Mol. Struct., 606, Nos. 1–3, 155 (2002).
B. B. Safoklov, E. G. Atovmyan, L. A. Nikonova, et al., Russ. Chem. Bull., 51, No. 12, 2224 (2002).
S. M. S. V. Wardell, M. V. N. De Souza, J. L. Wardell, et al., Acta Crystallogr., C62, No. 1, o47–o49 (2006).
A. Bacchi, A. Bonardi, M. Carcelli, et al., J. Inorg. Biochem., 69, Nos. 1/2, 101 (1998).
V. A. Knizhnikov, N. E. Borisova, N. Ya. Yurashevich, et al., Russ. J. Org. Chem., 43, No. 6, 855 (2007).
Bruker APEX2 Software Package, Bruker AXS, Madison (2005).
G. M. Sheldrik, SADABS, Program for Scanning and Correction of Area Detector Data, Univ. Göttingen, Germany (2004).
G. M. Sheldrick, Acta Crystallogr. A, 64, No. 1, 112 (2008).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT (2004).
P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem., 98, No. 45, 11623 (1994).
A. D. Becke, J. Chem. Phys., 98, No. 7, 5648 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, No. 2, 785 (1988).
S. Miertus, E. Scrocco, and J. Tomasi, Chem. Phys., 55, No. 1, 117 (1981).
R. Cammi and J. Tomasi, J. Comput. Chem., 16, No. 12, 1449 (1995).
G. A. Zhurko and D. A. Zhurko, Chemcraft Version 1.6 (build 338), http://www.chemcraftprog.com.
A. A. Shoukry and M. M. Shoukry, Spectrochim. Acta A, 70, No. 3, 686 (2008).
L. D. Popov, O. I. Askalepova, S. I. Levchenkov, and V. A. Kogan, Russ. J. Inorg. Chem., 52, No. 4, 626 (2007).
V. V. Sliznev and G. V. Girichev, J. Struct. Chem., 52, No. 1, 16 (2011).
M. P. Anderson and P. Uvdal, J. Phys. Chem. A, 109, No. 12, 2937 (2005).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text Copyright © 2013 by L. D. Popov, S. I. Levchenkov, I. N. Shcherbakov, M. A. Kiskin, N. E. Borisova, A. A. Tsaturyan, V. A. Kogan
__________
Translated from Zhurnal Strukturnoi Khimii, Vol. 54, No. 3, pp. 538–543, May–June, 2013.
Rights and permissions
About this article
Cite this article
Popov, L.D., Levchenkov, S.I., Shcherbakov, I.N. et al. Crystal structure of bis-Isonicotinoyl hydrazone of 2,5-diformylpyrrole. J Struct Chem 54, 592–597 (2013). https://doi.org/10.1134/S0022476613030190
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476613030190