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Crystal Structure and Conformation of 2-{(2′-Aminobenzyl)iminoethyl}- 5-methoxyphenol
-
D. K. Dey
and
Y. Elerman
Published/Copyright:
June 2, 2014
Abstract
The Schiff base, 2-{(2′-aminobenzyl)iminoethyl}-5-methoxyphenol, 1,2 -C6H4[NH2-2 ʹ]-CH2N=CHC6H3(OMe-5)OH (I), has been prepared by the reaction of 2 -amino-1-benzylamine and 2-hydroxy-4-methoxyacetophenone in methanol. The molecular structure has been confirmed by single crystal X-ray crystallography (triclinic, space group P 1̄, a = 7.201(2), b = 9.802(2), c = 9.993(2) Å, α = 83.09(2), β = 73.49(2), γ = 84.09(2)°, R = 0.0415 for 2611 independent reflections). The 1H and 13C NMR spectra in CDCI3 solution indicate the formation of some other minor conformations or dissociation in solution. The title compoundois not planar. Intramolecular hydrogen bonding occurs between O(1) and N(1) atoms [2.528(2) Å], the hydrogen atom essentially being bonded to the nitrogen atom. Minimum energy conformations from AMI were calculated as a function of four torsion angles. The optimized geometry of the molecular structure corresponding to the non-planar conformation is the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded hydrogen-hydrogen repulsions.
Received: 2000-12-12
Published Online: 2014-6-2
Published in Print: 2001-5-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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