Abstract
The crystal structures, solid-state infrared patterns, and thermal properties of two polymorphs of 4′-nitrosalicylanilide are presented. In both polymorphs, intramolecular hydrogen bonds are found between the phenol oxygen and the amide proton, and intermolecular hydrogen bonds are found between the amide carbonyl oxygen and the phenol proton. These hydrogen bond patterns are compared to those found in other known salicylamide derivatives and an analysis is given of the factors contributing to preferences for intra- or intermolecular hydrogen bonds in these structures. Crystal data:α polymorph, orthorhombic,Pbca,a=11.003(4),b=27.959(7),c=7.622(5) Å,Z=4,V=2345(3) Å3, andR=0.038 (1351 reflections);β polymorph, monoclinic,P21/a,a=28.36(1),b=11.64(1),c=7.293(8) Å,β=90.68(6)°,Z=8,V=2408 Å3, andR=0.043 (2425 reflections).
Similar content being viewed by others
References
Etter, M. C. (1985)Israel J. Chem. 25, 312.
Etter, M. C., Urbańczyk-Lipkowska, Z., Jahn, D. A., and Frye, J. S. (1986)J. Am. Chem. Soc. 108, 5871.
Etter, M. C., Urbańczyk-Lipkowska, Z., Fish, P. A., Panunto, T. W., Baures, P. W., and Frye, J. S. (1988)J. Crystallogr. Spectrosc. Res. 18, 311.
International Tables for X-Ray Crystallography, Vol. 3 (1962) (Kynoch Press, Birmingham, England).
Joesten, M. D., and Schaad, L. J. (1974)Hydrogen Bonding (Marcel Dekker, New York), Chap. 5.
Kashino, S., Matsushita, T., Iwamoto, T., Yamaguchi, K., and Haisa, M. (1986)Acta Crystallogr. C42, 457.
Panunto, T. W., Urbańczyk-Lipkowska, Z., Johnson, R., and Etter, M. C. (1987)J. Am. Chem. Soc. 109, 7786.
Sasada, Y., Takano, T., and Kakudo, M. (1964)Bull. Chem. Soc. Jpn. 37, 940.
Sindt, A. C., and Mackay, M. F. (1978)J. Cryst. Mol. Struct. 8, 17.
Sindt, A. C., and Mackay, M. F. (1979a)Acta Crystallogr. B35, 2103.
Sindt, A. C., and Mackay, M. F. (1979b)Acta Crystallogr. B35, 2452.
Sindt, A. C., and Mackay, M. F. (1979c)J. Cryst. Mol. Struct. 9, 265.
Sindt, A. C., and Mackay, M. F. (1980a)Aust. J. Chem. 33, 203.
Sindt, A. C., and Mackay, M. F. (1980b)Cryst. Struct. Comm. 33, 203.
Smeets, W. J. J., Kanters, J. A., and Venkatasubramanian, K. (1985)Acta Crystallogr. C41, 272.
Tanner, D. W., and Bruice, T. C. (1967)J. Am. Chem. Soc. 89, 6954.
Vyas, K., and Manohar, H. (1986)Mol. Cryst. Liq. Cryst. 137, 37.
Vyas, K., Mohan Rao, V., and Manohar, H. (1987)Acta Crystallogr. C43, 1201.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Etter, M.C., Urbańczyk-Lipkowska, Z., Ameli, T.M. et al. Intra- versus intermolecular hydrogen bonds in salicylamide derivatives. Journal of Crystallographic and Spectroscopic Research 18, 491–507 (1988). https://doi.org/10.1007/BF01161142
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01161142