Abstract
The title molecule is prepared by the Schiff base reaction. The structural properties of the compound are described using FTIR, 1H and 13C NMR, and absorption spectroscopies and single-crystal X-ray diffraction. Some quantum chemical calculations of the compound (molecular structure, vibrational wavenumbers and gauge including atomic orbital, 1H and 13C NMR chemical shifts) are executed using the density functional theory method at the B3LYP/6-311++G(d,p) level of theory. Additionally, electronic spectra of the compound are computed using the time-dependent density functional theory (TDDFT) method under the above conditions. A comparison of the experimental and theoretical findings reveals that a good correlation between them is acquired.
Similar content being viewed by others
REFERENCES
M. Köse, G. Ceyhan, M. Tümer, İ. Demirtaş, İ. Gönül, and V. McKee. Spectrochim. Acta, Part A, 2015, 137, 477–485.
Z. Demircioğlu, F. A. Özdemir, O. Dayan, Z. Şerbetçi, and N. Özdemir. J. Mol. Struct., 2018, 1161, 122–137.
A. C .V. of Aguiar, R. O. of Moura, J. F. B. Mendonça Jr., H. A. de Oliveira Rocha, R. B. G. Câmara, and M. dos Santos Carvalho Schiavon. Biomed. Pharmacother., 2016, 84, 403–414.
S. N. Pandeya, D. Sriram, G. Nath, and E. De Clercq. Pharm. Acta Helv., 1999, 74, 11–17.
K. Sztanke, A. Maziarka, A. Osinka, and M. Sztanke. Bioorg. Med. Chem., 2013, 21, 3648–3666.
P. G. Cozzi. Chem. Soc. Rev., 2004, 33, 410–421.
S. Dayan, N. K. Ozpozan, N. Özdemir, and O. Dayan, J. Organomet. Chem., 2014, 770, 21–28.
A. Tataroglu, R. Ocaya, A. Dere, O. Dayan, Z. Serbetci, A. G. Al-Sehemi, M. Soylu, A. A. Al-Ghamdi, and F. Yakuphanoglu. J. Electron. Mater., 2018, 47, 828–833.
A. Tataroğlu, O. Dayan, N. Özdemir, Z. Serbetci, A. A. Al-Ghamdi, A. Dere, F. El-Tantawy, and F. Yakuphanoglu. Dyes Pigm., 2016, 132, 64–71.
B. V. Kendre, M. G. Landge, W. N. Jadhav, and S. R. Bhusare. Chin. Chem. Lett., 2013, 24, 325–328.
L. M. Betts, N. C. Tam, S. M. H. Kabir, R. F. Langler, and I. Crandall. Aust. J. Chem., 2006, 59, 277–282.
H. Maeda, H. Matsuno, M. Ushida, K. Katayama, K. Saeki, and N. Itoh. Angew. Chem., Int. Ed. Engl., 2005, 44, 2922–2925.
M. W. van Gisbergen, M. Cebula, J. Zhang, A. Ottosson-Wadlund, L. Dubois, P. Lambin, K. D. Tew, D. M. Townsend, G. R. M. M. Haenen, M.-J. Drittij-Repders, H. Saneyoshi, M. Araki, Y. Shishido, Y. Ito, E. S. J. Arnér, H. Abe, R. Morgenstern, and K. Johansson. Mol. Pharm., 2016, 13, 2010–2025.
B. D. Cons, A. J. Bunt, C. D. Bailey, and C. L. Willis. Org. Lett., 2013, 15, 2046–2049.
Stoe and Cie. X-AREA Version 1.18, and X-RED32 Version 1.04. Stoe and Cie: Darmstadt, Germany, 2002.
G. M. Sheldrick. Acta Crystallogr., Sect. A, 2015, 71, 3–8.
G. M. Sheldrick. Acta Crystallogr., Sect. C, 2015, 71, 3–8.
L. J. Farrugia. J. Appl. Crystallogr., 2012, 45, 849–854.
A. D. Becke. J. Chem. Phys., 1993, 98, 5648–5652.
C. Lee, W. Yang, and R. G. Parr. Phys. Rev. B, 1988, 37, 785–789.
R. Ditchfield, W.J. Hehre, J.A. Pople. J. Chem. Phys., 1971, 54, 724–728.
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. Gaussian 09, Revision E.01. Gaussian, Inc.: Wallingford, CT, 2009.
R. Dennington, T. Keith, and J. Millam. Gauss View, Version 5.0. Semichem Inc.: Shawnee Mission, KS, 2009.
M. P. Andersson and P. Uvdal. J. Phys. Chem. A, 2005, 109, 2937–2941.
R. Ditchfield. J. Chem. Phys., 1972, 56, 5688–5691.
K. Wolinski, J. F. Hinton, and P. Pulay. J. Am. Chem. Soc., 1990, 112, 8251–8260.
E. Cancès, B. Mennucci, and J. Tomasi. J. Chem. Phys., 1997, 107, 3032–3041.
R. E. Stratmann, G. E. Scuseria, and M. J. Frisch. J. Chem. Phys., 1998, 109, 8218–8224.
M. E. Casida, C. Jamorski, K. C. Casida, and D. R. Salahub. J. Chem. Phys., 1998, 108, 4439–4449.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor. J. Chem. Soc., Perkin Trans., 1987, 2, S1–S19.
N. Özdemir, R. Kağıt, and O. Dayan. Mol. Phys., 2016, 114, 757–768.
D. Kand, P. S. Mandal, T. Saha, and P. Talukdar. RSC Adv., 2014, 4, 59579–59586.
Y.-N. Shen, L. Lin, H.-Y. Qiu, W.-Y. Zou, Y. Qian, and H.-L. Zhu. RSC Adv., 2015, 5, 23767–23777.
I. Kaabi, L. Sibous, T. Douadi, and S. Chafaa. J. Mol. Struct., 2015, 1084, 216–222.
K. M. Hutchins, S. Dutta, B. P. Loren, and L. R. MacGillivray. Chem. Mater., 2014, 26, 3042–3044.
J. Bernstein, R. E. Davis, L. Shimoni, and N.-L. Chang. Angew. Chem., Int. Ed. Engl., 1995, 34, 1555–1573.
A. Teimouri, A. N. Chermahini, K. Taban, and H. A. Dabbagh. Spectrochim. Acta, Part A, 2009, 72, 369–377.
H. A. Dabbagh, A. Teimouri, A. N. Chermahini, and M. Shahraki. Spectrochim. Acta, Part A, 2008, 69, 449–459.
R. M. Silverstein, G. C. Bassler, and T. C. Morill. Spectrometric Identification of Organic Compounds. 5th ed. Wiley: New York, 1991.
R. M. Silverstein, F. X. Webster, and D. J. Kiemle. Spectrometric Identification of Organic Compounds. 7th ed. John Wiley & Sons: New York, 2005.
N. P. G. Roeges. A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures. Wiley: New York, 1994.
N. M. O′Boyle, A. L. Tenderholt, and K. M. Langner. J. Comput. Chem., 2008, 29, 839–845.
Funding
This study was supported by Ondokuz Mayıs University (Project No. PYO.FEN.1906.19.001).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interests.
Rights and permissions
About this article
Cite this article
Özdemi, N., Dayan, O. SYNTHESIS, SPECTROSCOPY, X-RAY CRYSTALLOGRAPHY, AND DFT CALCULATIONS OF (E)-4-{[(2-HYDROXYPHENYL) IMINO]METHYL}PHENYL BENZENESULFONATE. J Struct Chem 61, 1575–1584 (2020). https://doi.org/10.1134/S0022476620100091
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476620100091