BibTex RIS Kaynak Göster

E -2-Bromo-4-Metoksi-6-[ P-Tolilimino Metil]Fenol Üzerine X-Işını, Ir, Molekül İçi Proton Transferi ve Kuantum Kimyasal Hesaplamalar

Yıl 2017, Cilt: 7 Sayı: 1, 92 - 101, 01.01.2017

Öz

Bu çalışmada, o-hidroksi Schiff Bazı türevi olan E -2-Bromo-4-metoksi-6-[ p-tolilimino metil]fenol molekülünün moleküler ve kristal yapısı tek kristal X-ışını kırınımı ve IR spektroskopileri ile karakterize edildi. Kuantum mekaniksel hesaplamalarda Yoğunluk Fonksiyoneli Teorisi B3LYP/6-31G d,p baz seti kullanılarak çalışmalarımız desteklendi. X-ışını kristalografisi verilerine göre bileşiğin katı halde fenol-imin tautomerik formu benimsediği gözlenmiştir.Molekülün iki tautomerik formu da DFT/B3LYP/6-31G d,p yöntemi kullanılarak incelenmiştir. Potansiyel enerji yüzeyi PES taraması OH tautomerik formun optimize geometrisi üzerinden gerçekleştirilmiştir ve içsel koordinat olarak O–H bağ uzunluğu kullanılmıştır. PES süreci, bizlere moleküler geometri üzerinde proton transferi etkilerini anlamak için yardımcı olur. Aynı zamanda bu çalışmada, molekülün doğrusal olmayan optik NLO özellikleri de incelenmiştir

Kaynakça

  • Albayrak, Ç., Kaştaş, G., Odabaşoğlu, M., Frank, R. 2013. The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-[(3- nitrophenylimino) methyl] phenol. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 114: 205-213.
  • Becke, AD., 1993. Density‐functional thermochemistry. III. The role of exact exchange. J. Chemic. Phys. 98(7): 5648-5652.
  • Bondi, A. 1964. van der Waals volumes and radii. J. Phys. Chem. 68(3): 441-451.
  • Calligaris, M., Nardin, G., Randaccio, L. 1972. Structural aspects of metal complexes with some tetradentate schiff bases. Coordin. Chem. Rev. 7(4): 385-403.
  • Calligaris, M., Randaccio, L. 1987. Compherensive Coordination Chemistry, vol. 2, in: G. Wilkinson (Ed.), Pergamon Press, London, pp. 715-738.
  • Cohen, MD., Schmidt, GM. J., Flavian, S. 1964. 388. Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes. J. Chem. Soc. (Resumed), 2041-2051.
  • Das, A., Trousdale, MD., Ren, S., Lien, EJ. 1999. Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of aminohydroxyguanidine tosylate. Antiv. Research, 44(3): 201-208.
  • Demircioğlu, Z., Kaştaş, ÇA., Büyükgüngör, O. 2015. The spectroscopic (FT-IR, UV–vis), Fukui function, NLO, NBO, NPA and tautomerism effect analysis of (E)-2-[(2-hydroxy6-methoxybenzylidene) amino] benzonitrile.Spectrochim. Acta Part A: Mol. Biomol. Spectrosc. 139: 539-548.
  • Dennington, R., Keith, T., Millam, J. 2009. Semichem Inc. Shawnee Mission KS, GaussView, Version, 5.
  • Farrugia, LJ., 1997. ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI). J. App. Crystalog. 30(5): 565-565.
  • Farrugia, LJ. 1999. WinGX suite for small-molecule singlecrystal crystallography. J. App. Crystallog. 32(4): 837-838.
  • Garnovskii, AD., Nivorozhkin, AL., Minkin, VI. 1993. Ligand environment and the structure of Schiff base adducts and tetracoordinated metal-chelates. Coord. Chem. Rev. 126(1): 1-69.
  • Gaussian, RA. 2009. 1, MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, G. Scalmani, V. Barone, B. Mennucci, GA Petersson et al., Gaussian. Inc., Wallingford CT.
  • Hadjoudis, E., Vittorakis, M., Moustakali-Mavridis, I. 1987. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahed. 43(7): 1345-1360.
  • Hadjoudis, E. 1995. Photochromic and thermochromic anils. Mol. Eng. 5(4): 301-337.
  • Hehre, WJ., Ditchfield, R., Pople, JA. 1972. Self—consistent molecular orbital methods. XII. Further extensions of gaussian—type basis sets for use in molecular orbital studies of organic molecules. J. Chem. Phys. 56(5): 2257-2261.
  • Jalali-Heravi, M., Khandar, AA., Sheikshoaie, I. 1999. A theoretical investigation of the structure, electronic properties and second-order nonlinearity of some azo Schiff base ligands and their monoanions. Spectrochim. Acta A. Mol. Biomol. Spectrosc. 55(12): 2537-2544.
  • Karadayı, N., Gözüyeşil, S., Guezel, B., Kazak, C., Büyükgüngör, O. 2003. N-[3, 5-Bis (trifluoromethyl) phenyl]-3-methoxysalicylaldimine. Acta Crystallogr. E, 59(6): o851-o853.
  • Kleinman, DA. 1962. Nonlinear dielectric polarization in optical media. Phys. Rev. 126(6): 1977.
  • Kosar, B., Albayrak, C. 2011. Spectroscopic investigations and quantum chemical computational study of (E)-4-methoxy2-[(p-tolylimino) methyl] phenol. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 78(1): 160-167.
  • Kruszewski, J., Krygowski, TM. 1972. Definition of aromaticity basing on the harmonic oscillator model. Tetrahed. Lett. 13(36): 3839-3842.
  • Krygowski, TM. 1993. Crystallographic studies of inter-and intramolecular interactions reflected in aromatic character of. pi.-electron systems. J. Chem. Inform. Comp. Scien., 33(1): 70- 78.
  • Lee, TC., Yang, WT., Parr, RG. 1988. Density-functional crystal orbital study on the structures and energetics of polyacetylene isomers. Phys. Rev. B, 37: 785-789.
  • Lozier, RH., Bogomolni, RA., Stoeckenius, W. 1975. Bacteriorhodopsin: a light-driven proton pump in Halobacterium Halobium. Biophys. J, 15(9): 955.
  • Maslen, H., Waters, TN. 1975. The conformation of Schiffbase complexes of copper (II): a stereo-electronic view. Coord. Chem. Rev. 17(2-3): 137-176.
  • Merrick, JP., Moran, D., Radom, L. 2007. An evaluation of harmonic vibrational frequency scale factors. J. Phys. Chem. A,111(45): 11683-11700.
  • Moustakali-Mavridis, IT., Hadjoudis, E., Mavridis, A. 1978. Crystal and molecular structure of some thermochromic Schiff bases. Acta Cryst. B. Struc. Crystalogr. Cryst. Chem. 34(12): 3709-3715.
  • Moustakali-Mavridis, I., Hadjoudis, B., Mavridis, A. 1980. Structure of thermochromic Schiff bases. II. Structures of N-salicylidene-3-aminopyridine and N-(5- methoxysalicylidene)-3-aminopyridine. Acta Crystallogr. B. Struct. Crystallogr. Cryst. Chem. 36(5): 1126-1130.
  • Nicoud, JF., Twieg, RJ. 1987. Design and synthesis of rganic molecular compounds for efficient second-harmonic generation. Non-linear. Optic. Propert. Org. Mol. Cryst. 1: 227- 296.
  • Papadopoulos, MG., Sadlej, AJ., Leszczynski, J. 2006. Nonlinear optic properties of matter. The Netherlands: Springer.
  • Petek, H., Albayrak, Ç., Ağar, E., Ískeleli, N. O., Şenel, İ. 2007. (E)-2-{1-[(4-Ethoxyphenyl) imino] ethyl} phenol. Acta Cryst. E: Struc. 63(2): o810-o812.
  • Rajamani, T., Muthu, S. 2013. Electronic absorption, vibrational spectra, non-linear optical properties, NBO analysis and thermodynamic properties of 9-[(2-hydroxyethoxy) methyl] guanine molecule by density functional method. Solid State Scien. 16: 90-101.
  • Ren, S., Tokes, ZA., Csipke, C., Zhou, B., Yen, Y., Lien, EJ. 2000. Inhibition of tumor cell growth by Schiff bases of hydroxysemicarbazide. Anti-cancer resear. 21(5): 3445-3451.
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, CE., Csipke, C., Tokes, Z. A., Lien, EJ. 2002. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. J. Medi. Chem., 45(2): 410-419.
  • Sahin, O., Albayrak, C., Odabaşoğlu, M., Büyükgüngör, O. 2005. (Z)-3-Hydroxy-6-[(2-methoxyphenylamino) methylene] cyclohexa-2, 4-dienone. Acta Cryst. E. 61(9): o2859- o2861.
  • Schlegel, HB. 1982. Optimization of equilibrium geometries and transition structures. J. Comp. Chem., 3(2): 214-218.
  • Scott, AP., Radom, L. 1996. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. The Journal of Physical Chemistry, 100(41): 16502-16513.
  • Sheldrick, GM. 2008. A short history of SHELX. Acta Cryst. A: Found. Cryst. 64(1): 112-122.
  • Stoe, C. 2002. X-area (version 1.18) and X-red32 (version 1.04). Stoe & Cie, Darmstadt, Germany.
  • Tanak, H., Toy, M. 2013. Molecular structure, vibrational spectra, NLO and MEP analysis of bis [2-hydroxy-κO-N-(2-pyridyl)- 1-naphthaldiminato-κN] zinc (II). Spectrochim. Acta A. Mol. Biomol. Spectro. 115: 145-153.
  • Yazıcı, S., Erşahin, F., Ağar, E., Şenel, İ., Büyükgüngör, O. 2009. 2-[(4-Chlorophenyl) iminomethyl] hydroquinone. Acta Cryst. E. 65(5): o1155-o1155.
  • Yüce, S., Özek, A., Albayrak, Ç., Odabaşoğlu, M., Büyükgüngör, O. 2004. 3-(4-Acetylphenyliminomethyl)-1, 2-dihydroxybenzene. Acta Cryst. E. 60(5): o810-o812.

Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol

Yıl 2017, Cilt: 7 Sayı: 1, 92 - 101, 01.01.2017

Öz

In this work, molecular and crystal structure of E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl] phenol which is an o-hydroxy Schiff base derivative was characterized by X-ray single crystal diffraction, IR spectroscopy. In the quantum mechanical calculations, the density functional theory B3LYP with 6-31G d, p was used to support our studies. According to the X-ray crystallographic data, the title compound adopted the phenol-imine tautomeric form in solid state.The two possible tautomeric forms of the title compound were investigated using DFT method with B3LYP applying 6-31G d, p basis set. A relaxed potantial energy surface PES scan was performed based on the optimized geometry of the OH tautomeric form and O–H bond distances were used as the redundant internal coordinate. PES scan process was helped us for understand the effects of transfer on the molecular geometry. At the same time, in this study, we were investigated nonlinear optical properties NLO of the title molecule.

Kaynakça

  • Albayrak, Ç., Kaştaş, G., Odabaşoğlu, M., Frank, R. 2013. The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-[(3- nitrophenylimino) methyl] phenol. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 114: 205-213.
  • Becke, AD., 1993. Density‐functional thermochemistry. III. The role of exact exchange. J. Chemic. Phys. 98(7): 5648-5652.
  • Bondi, A. 1964. van der Waals volumes and radii. J. Phys. Chem. 68(3): 441-451.
  • Calligaris, M., Nardin, G., Randaccio, L. 1972. Structural aspects of metal complexes with some tetradentate schiff bases. Coordin. Chem. Rev. 7(4): 385-403.
  • Calligaris, M., Randaccio, L. 1987. Compherensive Coordination Chemistry, vol. 2, in: G. Wilkinson (Ed.), Pergamon Press, London, pp. 715-738.
  • Cohen, MD., Schmidt, GM. J., Flavian, S. 1964. 388. Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes. J. Chem. Soc. (Resumed), 2041-2051.
  • Das, A., Trousdale, MD., Ren, S., Lien, EJ. 1999. Inhibition of herpes simplex virus type 1 and adenovirus type 5 by heterocyclic Schiff bases of aminohydroxyguanidine tosylate. Antiv. Research, 44(3): 201-208.
  • Demircioğlu, Z., Kaştaş, ÇA., Büyükgüngör, O. 2015. The spectroscopic (FT-IR, UV–vis), Fukui function, NLO, NBO, NPA and tautomerism effect analysis of (E)-2-[(2-hydroxy6-methoxybenzylidene) amino] benzonitrile.Spectrochim. Acta Part A: Mol. Biomol. Spectrosc. 139: 539-548.
  • Dennington, R., Keith, T., Millam, J. 2009. Semichem Inc. Shawnee Mission KS, GaussView, Version, 5.
  • Farrugia, LJ., 1997. ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI). J. App. Crystalog. 30(5): 565-565.
  • Farrugia, LJ. 1999. WinGX suite for small-molecule singlecrystal crystallography. J. App. Crystallog. 32(4): 837-838.
  • Garnovskii, AD., Nivorozhkin, AL., Minkin, VI. 1993. Ligand environment and the structure of Schiff base adducts and tetracoordinated metal-chelates. Coord. Chem. Rev. 126(1): 1-69.
  • Gaussian, RA. 2009. 1, MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, G. Scalmani, V. Barone, B. Mennucci, GA Petersson et al., Gaussian. Inc., Wallingford CT.
  • Hadjoudis, E., Vittorakis, M., Moustakali-Mavridis, I. 1987. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahed. 43(7): 1345-1360.
  • Hadjoudis, E. 1995. Photochromic and thermochromic anils. Mol. Eng. 5(4): 301-337.
  • Hehre, WJ., Ditchfield, R., Pople, JA. 1972. Self—consistent molecular orbital methods. XII. Further extensions of gaussian—type basis sets for use in molecular orbital studies of organic molecules. J. Chem. Phys. 56(5): 2257-2261.
  • Jalali-Heravi, M., Khandar, AA., Sheikshoaie, I. 1999. A theoretical investigation of the structure, electronic properties and second-order nonlinearity of some azo Schiff base ligands and their monoanions. Spectrochim. Acta A. Mol. Biomol. Spectrosc. 55(12): 2537-2544.
  • Karadayı, N., Gözüyeşil, S., Guezel, B., Kazak, C., Büyükgüngör, O. 2003. N-[3, 5-Bis (trifluoromethyl) phenyl]-3-methoxysalicylaldimine. Acta Crystallogr. E, 59(6): o851-o853.
  • Kleinman, DA. 1962. Nonlinear dielectric polarization in optical media. Phys. Rev. 126(6): 1977.
  • Kosar, B., Albayrak, C. 2011. Spectroscopic investigations and quantum chemical computational study of (E)-4-methoxy2-[(p-tolylimino) methyl] phenol. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 78(1): 160-167.
  • Kruszewski, J., Krygowski, TM. 1972. Definition of aromaticity basing on the harmonic oscillator model. Tetrahed. Lett. 13(36): 3839-3842.
  • Krygowski, TM. 1993. Crystallographic studies of inter-and intramolecular interactions reflected in aromatic character of. pi.-electron systems. J. Chem. Inform. Comp. Scien., 33(1): 70- 78.
  • Lee, TC., Yang, WT., Parr, RG. 1988. Density-functional crystal orbital study on the structures and energetics of polyacetylene isomers. Phys. Rev. B, 37: 785-789.
  • Lozier, RH., Bogomolni, RA., Stoeckenius, W. 1975. Bacteriorhodopsin: a light-driven proton pump in Halobacterium Halobium. Biophys. J, 15(9): 955.
  • Maslen, H., Waters, TN. 1975. The conformation of Schiffbase complexes of copper (II): a stereo-electronic view. Coord. Chem. Rev. 17(2-3): 137-176.
  • Merrick, JP., Moran, D., Radom, L. 2007. An evaluation of harmonic vibrational frequency scale factors. J. Phys. Chem. A,111(45): 11683-11700.
  • Moustakali-Mavridis, IT., Hadjoudis, E., Mavridis, A. 1978. Crystal and molecular structure of some thermochromic Schiff bases. Acta Cryst. B. Struc. Crystalogr. Cryst. Chem. 34(12): 3709-3715.
  • Moustakali-Mavridis, I., Hadjoudis, B., Mavridis, A. 1980. Structure of thermochromic Schiff bases. II. Structures of N-salicylidene-3-aminopyridine and N-(5- methoxysalicylidene)-3-aminopyridine. Acta Crystallogr. B. Struct. Crystallogr. Cryst. Chem. 36(5): 1126-1130.
  • Nicoud, JF., Twieg, RJ. 1987. Design and synthesis of rganic molecular compounds for efficient second-harmonic generation. Non-linear. Optic. Propert. Org. Mol. Cryst. 1: 227- 296.
  • Papadopoulos, MG., Sadlej, AJ., Leszczynski, J. 2006. Nonlinear optic properties of matter. The Netherlands: Springer.
  • Petek, H., Albayrak, Ç., Ağar, E., Ískeleli, N. O., Şenel, İ. 2007. (E)-2-{1-[(4-Ethoxyphenyl) imino] ethyl} phenol. Acta Cryst. E: Struc. 63(2): o810-o812.
  • Rajamani, T., Muthu, S. 2013. Electronic absorption, vibrational spectra, non-linear optical properties, NBO analysis and thermodynamic properties of 9-[(2-hydroxyethoxy) methyl] guanine molecule by density functional method. Solid State Scien. 16: 90-101.
  • Ren, S., Tokes, ZA., Csipke, C., Zhou, B., Yen, Y., Lien, EJ. 2000. Inhibition of tumor cell growth by Schiff bases of hydroxysemicarbazide. Anti-cancer resear. 21(5): 3445-3451.
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, CE., Csipke, C., Tokes, Z. A., Lien, EJ. 2002. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. J. Medi. Chem., 45(2): 410-419.
  • Sahin, O., Albayrak, C., Odabaşoğlu, M., Büyükgüngör, O. 2005. (Z)-3-Hydroxy-6-[(2-methoxyphenylamino) methylene] cyclohexa-2, 4-dienone. Acta Cryst. E. 61(9): o2859- o2861.
  • Schlegel, HB. 1982. Optimization of equilibrium geometries and transition structures. J. Comp. Chem., 3(2): 214-218.
  • Scott, AP., Radom, L. 1996. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. The Journal of Physical Chemistry, 100(41): 16502-16513.
  • Sheldrick, GM. 2008. A short history of SHELX. Acta Cryst. A: Found. Cryst. 64(1): 112-122.
  • Stoe, C. 2002. X-area (version 1.18) and X-red32 (version 1.04). Stoe & Cie, Darmstadt, Germany.
  • Tanak, H., Toy, M. 2013. Molecular structure, vibrational spectra, NLO and MEP analysis of bis [2-hydroxy-κO-N-(2-pyridyl)- 1-naphthaldiminato-κN] zinc (II). Spectrochim. Acta A. Mol. Biomol. Spectro. 115: 145-153.
  • Yazıcı, S., Erşahin, F., Ağar, E., Şenel, İ., Büyükgüngör, O. 2009. 2-[(4-Chlorophenyl) iminomethyl] hydroquinone. Acta Cryst. E. 65(5): o1155-o1155.
  • Yüce, S., Özek, A., Albayrak, Ç., Odabaşoğlu, M., Büyükgüngör, O. 2004. 3-(4-Acetylphenyliminomethyl)-1, 2-dihydroxybenzene. Acta Cryst. E. 60(5): o810-o812.
Toplam 42 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Article
Yazarlar

Serap Uzun

Çiğdem Albayrak Kaştaş Bu kişi benim

Orhan Büyükgüngör Bu kişi benim

İsmet Şenel Bu kişi benim

Yayımlanma Tarihi 1 Ocak 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 7 Sayı: 1

Kaynak Göster

APA Uzun, S., Kaştaş, Ç. A., Büyükgüngör, O., Şenel, İ. (2017). Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol. Karaelmas Fen Ve Mühendislik Dergisi, 7(1), 92-101.
AMA Uzun S, Kaştaş ÇA, Büyükgüngör O, Şenel İ. Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol. Karaelmas Fen ve Mühendislik Dergisi. Ocak 2017;7(1):92-101.
Chicago Uzun, Serap, Çiğdem Albayrak Kaştaş, Orhan Büyükgüngör, ve İsmet Şenel. “Combined X-Ray, IR, Intramolecular Proton Transfer and Quantum Chemical Studies on E -2-Bromo-4-Methoxy-6-[ P-Tolylimino methyl]phenol”. Karaelmas Fen Ve Mühendislik Dergisi 7, sy. 1 (Ocak 2017): 92-101.
EndNote Uzun S, Kaştaş ÇA, Büyükgüngör O, Şenel İ (01 Ocak 2017) Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol. Karaelmas Fen ve Mühendislik Dergisi 7 1 92–101.
IEEE S. Uzun, Ç. A. Kaştaş, O. Büyükgüngör, ve İ. Şenel, “Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol”, Karaelmas Fen ve Mühendislik Dergisi, c. 7, sy. 1, ss. 92–101, 2017.
ISNAD Uzun, Serap vd. “Combined X-Ray, IR, Intramolecular Proton Transfer and Quantum Chemical Studies on E -2-Bromo-4-Methoxy-6-[ P-Tolylimino methyl]phenol”. Karaelmas Fen ve Mühendislik Dergisi 7/1 (Ocak 2017), 92-101.
JAMA Uzun S, Kaştaş ÇA, Büyükgüngör O, Şenel İ. Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol. Karaelmas Fen ve Mühendislik Dergisi. 2017;7:92–101.
MLA Uzun, Serap vd. “Combined X-Ray, IR, Intramolecular Proton Transfer and Quantum Chemical Studies on E -2-Bromo-4-Methoxy-6-[ P-Tolylimino methyl]phenol”. Karaelmas Fen Ve Mühendislik Dergisi, c. 7, sy. 1, 2017, ss. 92-101.
Vancouver Uzun S, Kaştaş ÇA, Büyükgüngör O, Şenel İ. Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on E -2-Bromo-4-methoxy-6-[ p-tolylimino methyl]phenol. Karaelmas Fen ve Mühendislik Dergisi. 2017;7(1):92-101.