Ismail Erdem GÜMRÜKÇÜOĞLU, Ismet ŞENEL, Orhan BÜYÜKGÜNGÖR, Serap YAZICI, Çiğdem ALBAYRAK

(E)–2–acetyl–4–(4–methoxyphenyldiazenyl) phenol: X–ray and DFT–calculated structure

The crystal structure of the title compound, (E)-2-acetyl-4-(4-methoxyphenyldiazenyl) phenol, displays a trans configuration of the azo moiety as found for other azo (diazene) derivatives. The aromatic mean planes are nearly coplanar and the dihedral angle between the 2 aromatic rings is 3.04(8)◦ . The molecules, with strong intramolecular O–H. . . O hydrogen bonding, are linked by weak van der Waals interactions in the 3-dimensional network. The molecular geometry, determined using X-ray diffraction techniques, was also calculated with the density functional theory (DFT), employing the hybrid exchange-correlation functional B3LYP. Experimental and theoretical IR spectra of the compound were also calculated for comparison. The results of the experimental and theoretical calculations are compared in this study.

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1. Peter, A. T.; Freeman, H. S. Colour Chemistry, The Design and Synthesis of Organic Dyes and Pigments, Elsevier, Barking, Essex, England, 1991.
2. Jeon, B. J.; Cha, S. W.; Jeong, M. Y.; Lim, T. K.; Jin, J. I. J. Mater. Chem. 2002, 12, 546-552.
3. Tian, Z. Y.; Huang, W. T.; Xiao, D. B.; Wang, S. Q.; Wu, Y. S.; Gong, Q. H. Chem. Phys. Lett. 2004, 391, 283.
4. Biswas, N.; Umapathy, S. J. Phys. Chem. 2000, A104, 2734-2745.
5. Stoe & Cie. X-AREA (Version 1.18) and X-RED32 (Version 1.04), Darmstadt, Germany, 2002.
6. Sheldrick, G. M. SHELXS 97 and SHELXL 97, Program for Crystal Structure Solution and Refinement, University of Göttingen, Germany, 1997.
7. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789.
8. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
9. Frisch, M. D.; et al. GAUSSIAN 03W, Revision E. 01, Wallingford, Connecticut, Gaussian, Inc., 2004.
10. Farrugia, L. J. ORTEP-3 for Windows, Dept. of Chemistry, University of Glasgow, UK, 1998.
11. Huang, X. J.; Kuhn, G. H.; Nesterov, V. N.; Averkiev, B. B.; Penn, B.; Antipin, M. Yu.; Timofeeva, T. V. Acta Cryst. 2002, C58, o624-o628.
12. Koşar, B.; Albayrak, Ç .; Odabaşoğlu, M.; Büyükgüngör, O. Acta Cryst. 2004, E60, o190-o192.
13. Basu-Baul, T. S.; Kundu, S.; Arman, H. D.; Tiekink, E. R. T. Acta Cryst. 2009, E65, o3061.
14. Minisini, B.; Fayet, G.; Tsobnang, F.; Bardeau, J. F. J. Mol. Model. 2007, 13, 1227- 1235.
15. Loudon, M. G. Organic Chemistry, 4th ed., Oxford University Press, 2002, p. 837.
16. Krygowski, T. M. J. Chem. Inf. Comput. Sci. 1993, 33, 70-78.
17. Kruszewski, J.; Krygowski, T. M. Tetrahedron Lett. 1972, 13, 3839-3842.
18. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
19. Mulliken, R. S. J. Chem. Phys. 1962, 36, 3428.
20. Aihara, J. J. Phys. Chem. 1999, A103, 7487.
21. Kim, K. H.; Han, Y. K.; Jung, J. Theor. Chem. Acc. 2005, 113, 233.
22. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. 2007, A111, 11683-11700.
23. Karaer, H.; Gümrükçüoğlu, İ. E. Turk. J. Chem. 1999, 23, 61-71.
24. Karcı, F.; Demirçalı, A.; Şener, İ.; Tilki, T. Dyes and Pigments 2006, 71, 90-96.
25. Albayrak, Ç .; Gümrükçüoğlu, İ. E.; Odabaşoğlu, M.; İskeleli, N. O.; Ağar, E. J. Mol. Strct. 2009, 932, 43-54.