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

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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.

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ACKNOWLEDGMENTS

We thank c* change (PAR-08), ESKOM (TESP program), and the National Research Foundation (NRF) for financial support. In addition, Sizwe J. Zamisa is acknowledged for the collection and refinement of crystallographic data.

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  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, 4000, Durban, South Africa

    A. N. W. Kadafour & M. D. Bala

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  1. A. N. W. Kadafour
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  2. M. D. Bala
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Correspondence to M. D. Bala.

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Kadafour, A.N., Bala, M.D. Crystal Structure of (E)-1-(((3-nitrophenyl)imino)methyl)naphthalen-2-ol. Crystallogr. Rep. 67, 214–217 (2022). https://doi.org/10.1134/S1063774522020055

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  • DOI: https://doi.org/10.1134/S1063774522020055

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