Abstract
2-((E)-((2-(((E)-2-hydroxy-3-methylbenzylidene)amino)benzyl)imino)methyl)-6-methylphenol, C23H22N2O2, was synthesized by the reaction between 2-hydroxy-3-methylbenzaldehyde, and 2-(aminomethyl)aniline in aqueous ethanol. X-ray diffraction analysis technique was used to reveal the structure. The crystal structure is monoclinic, space group P21/c with parameters a = 4.6035(11) Å, b = 18.895(3) Å, c = 21.748(6) Å, β = 100.23(4)°, V = 1794(16) Å3, Z = 4. It was determined by the Hirshfeld surface study that intermolecular hydrogen bonds stabilized the complex structure. Structure verified by Fourier transform infrared spectra technique.
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REFERENCES
H. Schiff. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen. Ann. Chem. Pharm., 1864, 131(1), 118/119. https://doi.org/10.1002/jlac.18641310113
N. Dege, A. S. Aydın, E. Ağar, S. Kansız, S. JoseKavitha, K. BalaSubramani, M. Hemamalini, and V. Rajakannan. Synthesis, crystal structure, Hirshfeld surface analysis, in-silico assessment of druggability and molecular docking studies of Schiff base compound. Chem. Data Collect., 2020, 25, 100320. https://doi.org/10.1016/j.cdc.2019.100320
A. Jarrahpour, D. Khalili, E. De Clercq, C. Salmi, and J. Brunel. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules, 2007, 12(8), 1720-1730. https://doi.org/10.3390/12081720
C. M. da Silva, D. L. da Silva, L. V. Modolo, R. B. Alves, M. A. de Resende, C. V. B. Martins, and Â. de Fátima. Schiff bases: A short review of their antimicrobial activities. J. Adv. Res., 2011, 2(1), 1-8. https://doi.org/10.1016/j.jare.2010.05.004
M. A. Ashraf, K. Mahmood, A. Wajid, M. J. Maah, and I. Yusoff. Synthesis, characterization and biological activity of Schiff bases. Int. Proc. Chem., Biol. Environ. Eng., 2011, 10(1), 185.
P. G. Cozzi. Metal–salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev., 2004, 33(7), 410-421. https://doi.org/10.1039/b307853c
H. Ashassi-Sorkhabi, B. Shabani, B. Aligholipour, and D. Seifzadeh. The effect of some Schiff bases on the corrosion of aluminum in hydrochloric acid solution. Appl. Surf. Sci., 2006, 252(12), 4039-4047. https://doi.org/10.1016/j.apsusc.2005.02.148
Z. Quan, S. Chen, and S. Li. Protection of copper corrosion by modification of self-assembled films of Schiff bases with alkanethiol. Corros. Sci., 2001, 43(6), 1071-1080. https://doi.org/10.1016/s0010-938x(00)00131-1
X-RED and X-AREA. Darmstadt, Germany: Stoe & Cie, 2009.
G. M. Sheldrick. A short history of SHELX. Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64(1), 112-122. https://doi.org/10.1107/s0108767307043930
G. M. Sheldrick. A short history of SHELX. Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64(1), 112-122. https://doi.org/10.1107/s0108767307043930
M. Turner, J. McKinnon, S. Wolff, D. Grimwood, P. Spackman, D. Jayatilaka, and M. A. Spackman. CrystalExplorer17, Version 5. Perth, Australia: University of Western Australia, 2017.
R. Dennington II, T. Keith, and J. Millam. GaussView, Version 5. Shawnee Mission, KS, USA: Semichem Inc., 2009.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox. Gaussian09, Revision A.02. Wallingford, CT, USA: Gaussian, Inc., 2009.
P. L. Fast, J. Corchado, M. L. Sanchez, and D. G. Truhlar. Optimized parameters for scaling correlation energy. J. Phys. Chem. A, 1999, 103(17), 3139-3143. https://doi.org/10.1021/jp9900382
A. D. Becke. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys., 1993, 98(7), 5648-5652. https://doi.org/10.1063/1.464913
C. Lee, W. Yang, and R. G. Parr. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 1988, 37(2), 785-789. https://doi.org/10.1103/physrevb.37.785
K. U. Ambili, S. S. Sreejith, J. M. Jacob, M. Sithambaresan, and M. R. P. Kurup. 2-Ethoxy-6-({2-[(3-ethoxy-2-hydroxybenzylidene)amino]benzyl}iminomethyl)phenol. Acta Crystallogr., Sect. E: Struct. Rep. Online, 2012, 68(8), o2482. https://doi.org/10.1107/s1600536812031479
D. K. Dey, S. P. Dey, A. Elmali, and Y. Elerman. Molecular structure and conformation of N-2-[3′-(methoxysalicylideneimino)benzyl]-3″-methoxysalicylideneimine. J. Mol. Struct., 2001, 562(1-3), 177-184. https://doi.org/10.1016/s0022-2860(00)00970-4
S. L. Bernstein, N. F. Dupuis, N. D. Lazo, T. Wyttenbach, M. M. Condron, G. Bitan, D. B. Teplow, J.-E. Shea, B. T. Ruotolo, C. V. Robinson, and M. T. Bowers. Amyloid-β protein oligomerization and the importance of tetramers and dodecamers in the aetiology of Alzheimer′s disease. Nat. Chem., 2009, 1(4), 326-331. https://doi.org/10.1038/nchem.247
A. Teimouri, A. N. Chermahini, K. Taban, and H. A. Dabbagh. Experimental and CIS, TD-DFT, ab initio calculations of visible spectra and the vibrational frequencies of sulfonyl azide-azoic dyes. Spectrochim. Acta, Part A, 2009, 72(2), 369-377. https://doi.org/10.1016/j.saa.2008.10.006
H. A. Dabbagh, A. Teimouri, A. Najafi Chermahini, and M. Shahraki. DFT and ab initio study of structure of dyes derived from 2-hydroxy and 2,4-dihydroxy benzoic acids. Spectrochim. Acta, Part A, 2008, 69(2), 449-459. https://doi.org/10.1016/j.saa.2007.04.024
A. Teimouri, M. Emami, A. N. Chermahini, and H. A. Dabbagh. Spectroscopic, quantum chemical DFT/HF study and synthesis of [2.2.1] hept-2′-en-2′-amino-N-azatricyclo [3.2.1.02,4] octane. Spectrochim. Acta, Part A, 2009, 71(5), 1749-1755. https://doi.org/10.1016/j.saa.2008.06.043
G. Socrates. Infrared and Raman Characteristic Group Frequencies. Blackwell, New Jersey, USA: Wiley, 2004.
R. Lu, W. Gan, B. Wu, Z. Zhang, Y. Guo, and H. Wang. C–H stretching vibrations of methyl, methylene and methine groups at the vapor/alcohol (n = 1–8) interfaces. J. Phys. Chem. B, 2005, 109(29), 14118-14129. https://doi.org/10.1021/jp051565q
H. Saraçoğlu and A. Cukurovali. Crystal structure, spectroscopic investigations, and density functional studies of (Z)-2-(1H-imidazol-1-yl)-1-(3-methyl-3-mesitylcyclobutyl)ethanone oxime. Mol. Cryst. Liq. Cryst., 2016, 625(1), 173-185. https://doi.org/10.1080/15421406.2015.1069443
H. Saraçoğlu and A. Cukurovali. An experimental and theoretical approach to the molecular structure of 3-{[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazono}-1,3-dihydro-indol-2-one. Int. J. Quantum Chem., 2012, 112(6), 1566-1578. https://doi.org/10.1002/qua.23136
D. Lin-Vein, N. B. Colthup, W. G. Fateley, and J. G. Grasselli. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules. New York, USA: Academic, 1991.
I. H. Joe, G. Aruldhas, S. Anbukumar, and P. Ramasamy. Vibrational spectra and phase transition in triglycine sulpho-phosphate. Cryst. Res. Technol., 1994, 29(5), 685-692. https://doi.org/10.1002/crat.2170290520
H. Saraçoğlu and Ö. Ekici. Spectroscopic characterization, X-ray structure and DFT studies on 4-[3-(2,5-dimethylphenyl)-3-methylcyclobutyl]-N-methylthiazol-2-amine. J. Struct. Chem., 2015, 56(7), 1342-1352. https://doi.org/10.1134/s002247661507015x
K. Furić, V. Mohaček, M. Bonifačić, and I. Štefanić. Raman spectroscopic study of H2O and D2O water solutions of glycine. J. Mol. Struct., 1992, 267, 39-44. https://doi.org/10.1016/0022-2860(92)87006-h
G. Lan, H. Wang, and J. Zheng. Raman spectra of diglycine selenate crystals. Spectrochim. Acta, Part A, 1990, 46(8), 1211-1216. https://doi.org/10.1016/0584-8539(90)80197-7
H. Ünver, C. T. Zeyrek, B. Boyacioglu, M. Yıldız, N. Demir, and A. Elmali. Synthesis, crystal structure, anion sensing applications and DFT studies of (E)-2-[(3,5-bis(trifluoromethyl)phenylimino)methyl]-4-chlorophenol. J. Chem. Crystallogr., 2019, 49(4), 232-244. https://doi.org/10.1007/s10870-018-0758-7
F. Güntepe, H. Saraçoğlu, N. Çalıskan, Ç. Yüksektepe, and A. Çukurovalı. Structure and DFT calculations of 2-{[3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenol. J. Struct. Chem., 2011, 52(3), 596-601. https://doi.org/10.1134/s002247661103022x
A. J. Barnes, M. A. Majid, M. A. Stuckey, P. Gregory, and C. V. Stead. The resonance Raman spectra of Orange II and Para Red: molecular structure and vibrational assignment. Spectrochim. Acta, Part A, 1985, 41(4), 629-635. https://doi.org/10.1016/0584-8539(85)80050-7
D. Sathiyanarayanan. Vibrational Spectroscopy Theory and Application. New Delhi, India: New Age International, 2004.
J. George, J. C. Prasana, S. Muthu, T. K. Kuruvilla, S. Sevanthi, and R. S. Saji. Spectroscopic (FTIR, FT Raman) and quantum mechanical study on N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide. J. Mol. Struct., 2018, 1171, 268-278. https://doi.org/10.1016/j.molstruc.2018.05.106
A. Karmakar and B. Singh. Spectroscopic and theoretical studies of charge-transfer interaction of 1-(2-pyridylazo)-2-napthol with nitroaromatics. Spectrochim. Acta, Part A, 2017, 179, 110-119. https://doi.org/10.1016/j.saa.2017.01.047
N. Issaoui, H. Ghalla, S. A. Brandán, F. Bardak, H. T. Flakus, A. Atac, and B. Oujia. Experimental FTIR and FT-Raman and theoretical studies on the molecular structures of monomer and dimer of 3-thiopheneacrylic acid. J. Mol. Struct., 2017, 1135, 209-221. https://doi.org/10.1016/j.molstruc.2017.01.074
P. Manjusha, J. C. Prasana, S. Muthu, and B. Raajaraman. Density functional studies and spectroscopic analysis (FT-IR, FT-Raman, UV-visible, and NMR) with molecular docking approach on an antifibrotic drug pirfenidone. J. Mol. Struct., 2020, 1203, 127394. https://doi.org/10.1016/j.molstruc.2019.127394
D. M. Gil. Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone. J. Mol. Struct., 2020, 1205, 127589. https://doi.org/10.1016/j.molstruc.2019.127589
N. Boukabcha, A. Direm, M. Drissi, Y. Megrouss, N. Khelloul, N. Dege, M. Tuna, and A. Chouaih. Synthesis, structural determination, Hirshfeld surface analysis, 3D energy frameworks, electronic and (static, dynamic) NLO properties of o-Nitroacetanilide (o-NAA): A combined experimental and quantum chemical study. Inorg. Chem. Commun., 2021, 133, 108884. https://doi.org/10.1016/j.inoche.2021.108884
D. A. Kleinman. Nonlinear dielectric polarization in optical media. Phys. Rev., 1962, 126(6), 1977-1979. https://doi.org/10.1103/physrev.126.1977
A. D. Buckingham. Basic Theory of Intermolecular Forces: Applications to Small Molecules. In: Intermolecular Interactions: From Diatomics to Biopolymers / Ed. B. Pullman. New York, USA: Wiley, 1978, Vol. 1, 1.
H. Saraçoğlu and A. Cukurovali. Quantum chemical, spectroscopic and X-ray diffraction studies of 5-methoxy-2-({4-[3-methyl-3-mesityl-cyclobutyl]-thiazol-2-yl}-hydrazonomethyl)-phenol. J. Mol. Struct., 2013, 1048, 382-391. https://doi.org/10.1016/j.molstruc.2013.06.009
Y.-X. Sun, Q.-L. Hao, W.-X. Wei, Z.-X. Yu, L.-D. Lu, X. Wang, and Y.-S. Wang. Experimental and density functional studies on 4-(2,3-dichlorobenzylideneamino)antipyrine and 4-(2,5-dichlorobenzylideneamino)antipyrine. J. Mol. Struct., 2009, 929(1-3), 10-21. https://doi.org/10.1016/j.molstruc.2009.03.035
R. Zhang, B. Du, G. Sun, and Y. Sun. Experimental and theoretical studies on o-, m- and p-chlorobenzylideneaminoantipyrines. Spectrochim. Acta, Part A, 2010, 75(3), 1115-1124. https://doi.org/10.1016/j.saa.2009.12.067
Y.-X. Sun, Q.-L. Hao, Z.-X. Yu, W.-X. Wei, L.-D. Lu, and X. Wang. Experimental and density functional studies on 4-(4-cyanobenzylideneamino)antipyrine. Mol. Phys., 2009, 107(3), 223-235. https://doi.org/10.1080/00268970902769471
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Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 6, 112737.https://doi.org/10.26902/JSC_id112737
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Doğan, O.E., Poyraz, E.B., Saraçoğlu, H. et al. Structural, Spectroscopic and Molecular Characterization of an Asymmetric Schiff Base Compound. J Struct Chem 64, 1147–1163 (2023). https://doi.org/10.1134/S0022476623060161
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DOI: https://doi.org/10.1134/S0022476623060161