Abstract
Four Schiff base molecules were synthesized from the condensation of 2-hydroxy-1-naphthaldehyde with various amines having additional ligating centers, and the resulting products were characterized by analytical and spectral methods, and also by single crystal X-ray diffraction. 2-(β-Naphthalideneamino)-2-methyl-1-propanol, 1, is orthorhombic, P212121, a = 9.918(1), b = 12.629(1), c = 10.416(1) Å. 2-(β-Naphthalideneamino)-2-hydroxymethyl-1-propanol, 2, is monoclinic, P21/c, a = 14.522(3), b = 9.723(2), c = 9.534(9) Å, β = 107.75(4)°. 2-(β-Naphthalideneamino)-2-hydroxymethyl-1,3-propanediol, 3, is monoclinic, P21/c, a = 20.981(9), b = 5.943(3), c = 10.549(5) Å, β = 91.23(3)°. 2-(β-Naphthalideneamino)-pyridine, 4, is monoclinic, P21/c, a = 5.804(4), b = 17.363(2), c = 24.032(11) Å, β = 92.03(5)°. The molecular structures of these were found to be in extended conformation where the aromatic moiety is coplanar with that of the imine bond and the imine bond exhibited trans-geometry. The naphthyl moiety in each of these molecules is stabilized in quinoid form in the solid state. Interesting lattice structures were noticed owing to intermolecular interactions.
Similar content being viewed by others
References
Schiff, H. Ann. Chim. (Paris) 1864, 131, 118.
Calligaris, M.; Randaccio, L. In Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R.D.; McCleverty, J.A., Eds.; Pergamon: Oxford, 1987; Vol. 2, Ch. 20.1, p 715.
Rao, P.V.; Rao, C.P.; Wegeilus, E.K.; Kolehmainen, E.; Rissanen, K. J. Chem. Soc., Dalton Trans. 1999, 4469.
Rao, C.P.; Sreedhara, A.; Rao, P.V. Polyhedron 1999, 18, 289.
Rao, C.P.; Sreedhara, A.; Rao, P.V.; Verghese, B.M.; Kolehmainen, E.; Lokanath, N.K.; Sridhar, M.A.; Prasad, J.S. J. Chem. Soc., Dalton Trans. 1998, 2383.
Rao, P.V.; Rao, C.P.; Sreedhara, A.; Wegeilus, E.K.; Kolehmainen, E.; Rissanen, K. J. Chem. Soc., Dalton Trans. 2000, 1213.
Duff, J.C. J. Chem. Soc. 1935, 1305.
Sheldrick, G.M. SHELX83, Program for Crystal Structure Solution; Institüt für Anorganische Chemie der Universität: Göttingen, Germany, 1986.
Sheldrick, G.M. SHELXL93, Program for Crystal Structure Refinement; Institüt für Anorganische Chemie der Universität: Göttingen, Germany, 1993.
Burnett, M.N.; Jhonson, C.K. ORTEP-III, Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, Tennessee, 1996.
Spek, A.L. Acta Crystallogr., Sect A 1990, 46, C34.
Spek, A.L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 1998.
Moustakali-Mavridis, I.; Hadjoudis, E. Acta Crystallogr., Sect. C. 1983, 39, 365.
Bregman, J.; Leiserowitz, L.; Schmidt, G.M.J. J. Chem. Soc. 1964, 2068.
Percy, G.C.; Thornton, D.A. J. Inorg. Nucl. Chem. 1972, 34, 3357, 3369.
Asgedom, G.; Sreedhara, A.; Kivikoski, J.; Valkonen, J.; Kolehmainen, E.; Rao, C.P. Inorg. Chem. 1996, 35, 5674.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rao, P.V., Rao, C.P., Wegelius, E.K. et al. 2-hydroxy-1-naphthaldehyde-derived Schiff bases: synthesis, characterization, and structure. Journal of Chemical Crystallography 33, 139–147 (2003). https://doi.org/10.1023/A:1023226925997
Issue Date:
DOI: https://doi.org/10.1023/A:1023226925997