Abstract
The crystal structure of the title compound, C14H12N2O3, was recently determined as a mixture of its neutral (OH containing) and zwitterionic (NH containing) forms, in a 0.60 (4): 0.40 (4) ratio using the X-ray determination. In this study, the title compound has been characterized by FT-IR and X-ray diffraction. The redetermination showed that the title compound has only enol (OH) form because of lack of the NH stretching vibration in FT-IR spectrum. In addition, the molecular structure and tautomerism of the title compound have been discussed.
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References
D. Barton and W. D. Ollis, Comprehensive Organic Chemistry (Pergamon, Oxford, 1979), Vol. 2.
R. W. Layer, Chem. Rev. 63, 489 (1963).
C. K. Ingold, Structure and Mechanısm in Organıc Chemistry, 2nd ed. (Corneh Univ. Press, Ithaca, 1969).
H. Tanak, M. Yavuz, and O. Büyükgüngör, Acta Crystallogr. E 65, o2949 (2009).
F. Aydoğan, N. Öcal, Z. Turgut, et al., Bull. Korean Chem. Soc. 22, 476 (2001).
H. Tanak, F. Toğurman, S. Kalecik, et al., Acta Crystallogr. E 69, 1085 (2013).
A. E. Taggi, E. Hafez, A. M. Wack, et al., J. Am. Chem. Soc. 124, 6626 (2002).
M. D. Cohen, G. M. J. Schmidt, and S. Flavian, J. Chem. Soc. 2041–2051 (1964).
E. Hadjoudis, M. Vitterakis, I. Moustakali, et al., Tetrahedron 43, 1345 (1987).
H. Tanak, Y. Bingöl Alparslan, M. Yavuz, et al., Acta Crystallogr. E 65, o1572 (2009).
H. Tanak, M. Macit, M. Yavuz, et al., Acta Crystallogr. E 65, o3056 (2009).
M. N. Tahir, H. A. Shad, and R. H. Tariq, Acta Crystallogr. E 67, o2319 (2011).
Stoe & Cie X-AREA (Version 1.18) X-RED32 (Version 1.04) (Stoe&Cie, Darmstadt, Germany, 2002).
G. M. Sheldrick, SHELXS97 (Univ. of Göttingen, Göttingen, 1997).
G. M. Sheldrick, SHELXL-97, Program for Crystal Structures Refinement (Univ. of Göttingen, Göttingen, 1997).
L. J. Farrugia, J. Appl. Crystallogr. 30, 565 (1997)
H. Tanak, F. Erşahin, E. Ağar, et al., Acta Crystallogr. E 65, o2291 (2009).
H. Tanak, A. A. Agar, and O. Büyükgüngör, Spectrochim. Acta A 87, 15 (2012).
Y. Hijji, S. Azemati, R. J. Butcher, et al., Acta Crystallogr. E 70, o451 (2014).
J. Bernstein, R. E. Davies, L. Shimoni, et al., Angew. Chem. Int. Ed. Engl. 34, 1555 (1995).
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Kaynar, N.K., Tanak, H., Şahin, S. et al. Molecular and crystal structure of 2-{(E)-[(4-Methylphenyl)imino]methyl}-4-nitrophenol: A redetermination. Crystallogr. Rep. 61, 239–242 (2016). https://doi.org/10.1134/S1063774516020097
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DOI: https://doi.org/10.1134/S1063774516020097