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Crystal Structure of (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol

Crystal Structure of (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol Formation of the title Schiff base compound (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol, C17H12N2O3 (1) was achieved by the condensation of 2-hydroxy-1-naphthaldehyde and 3-nitroaniline and confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet–visible spectroscopy and single-crystal X-ray diffraction. Compound 1 belongs to the orthorhombic system, space group P212121 and has intramolecular hydrogen bonds O–H⋅⋅⋅N and N–H⋅⋅⋅O. X-ray data also revealed a resonance structure that contains the equilibrium of imine-phenol (OH)/keto-amine (NH) tautomers of 1. However, spectroscopic data in common solvents and Hirshfeld surface analysis showed the predominance of the OH tautomer over the NH form of the Schiff base in solution. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Crystallography Reports Springer Journals

Crystal Structure of (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol

Kadafour, A. N. W.; Bala, M. D.
Crystallography Reports , Volume 67 (2) – Apr 1, 2022
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References (18)

Publisher
Springer Journals
Copyright
Copyright © Pleiades Publishing, Inc. 2022. ISSN 1063-7745, Crystallography Reports, 2022, Vol. 67, No. 2, pp. 214–217. © Pleiades Publishing, Inc., 2022.
ISSN
1063-7745
eISSN
1562-689X
DOI
10.1134/s1063774522020055
Publisher site
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Abstract

Formation of the title Schiff base compound (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol, C17H12N2O3 (1) was achieved by the condensation of 2-hydroxy-1-naphthaldehyde and 3-nitroaniline and confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet–visible spectroscopy and single-crystal X-ray diffraction. Compound 1 belongs to the orthorhombic system, space group P212121 and has intramolecular hydrogen bonds O–H⋅⋅⋅N and N–H⋅⋅⋅O. X-ray data also revealed a resonance structure that contains the equilibrium of imine-phenol (OH)/keto-amine (NH) tautomers of 1. However, spectroscopic data in common solvents and Hirshfeld surface analysis showed the predominance of the OH tautomer over the NH form of the Schiff base in solution.

Journal

Crystallography Reports – Springer Journals

Published: Apr 1, 2022

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