2-Hydroxy-1-naphthaldehyde-derived Schiff bases: Synthesis, characterization, and structure

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2-Hydroxy-1-naphthaldehyde-derived Schiff bases: Synthesis, characterization, and structure

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Title: 2-Hydroxy-1-naphthaldehyde-derived Schiff bases: Synthesis, characterization, and structure
Author: RAO, PV; RAO, CP; WEGELIUS, EK; RISSANEN, K
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-(beta-Naphthalideneamino)-2-methyl-1- propanol, 1, is orthorhombic, P2(1)2(1)2(1), a = 9.918(1), b = 12.629(1), c = 10.416(1) Angstrom. 2(beta-Naphthalideneamino)-2-hydroxymethyl-1-propanol, 2, is monoclinic, P2(1)/c, a = 14.522(3), b = 9.723(2), c = 9.534(9) Angstrom, = beta 107.75(4)degrees. 2-(beta-Naphthalideneamino)-2-hydroxymethyl-1,3-propanediol, 3, is monoclinic, P2(1)/c, a = 20.981(9), b = 5.943(3), c = 10.549(5) Angstrom, beta = 91.23(3)degrees. 2-(beta-Naphthalideneamino)-pyridine, 4, is monoclinic, P2(1)/c, a = 5.804(4), b = 17.363(2), c = 24.032(11) Angstrom, beta = 92.03(5)degrees. 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.
URI: http://dx.doi.org/10.1023/A:1023226925997
http://dspace.library.iitb.ac.in/xmlui/handle/10054/9818
http://hdl.handle.net/10054/9818
Date: 2003


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