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Characterization of solvent effects on C=O stretching vibrations of ketoprofen by empirical solvent parameters
Abstract
The solvent effects on C=O stretching vibrational frequency, ν(C=O), of ketoprofen (KETO) were studied experimentally using attenuated total reflection infrared spectroscopy (ATR-IR). The experimental ν(C=O) of KETO were correlated with empirical solvent parameters, including the Kirkwood–Bauer–Magat (KBM) equation, the acceptor numbers (ANs) of the solvents, the Swain equation, linear solvation energy relationships (LSERs), and the quadratic equation (QE). The solvent-induced ν(C=O) shifts of KETO displayed a better correlation with the LSER equation than with the KBM equation, ANs of the solvents, and the Swain equation. The linear effect of the solvent hydrogen-bond donor acidity (Aj) on ν(C=O) of KETO was found to be highly significant, whereas the hydrogen-bond acceptor basicity (Bj) and the interaction effect of Aj and Bj were not significant. It was also observed that the quadratic effects of Aj and Bj were slightly significant. Additionally, the linear effect of LSER parameters (π*, δ, α , and β) and the interaction effect of π* β on the ν(C=O) of KETO were highly significant.
Keywords
ketoprofen,
solvent effect,
Swain equation,
linear solvation energy relationship,
quadratic equation
Supporting agencies: . The authors would like to thank the Kocaeli University Research Fund for financial support (Grant No. 2012/069).
About the Authors
S. Sagdinc
Kocaeli University
Turkey
Turkey
Kocaeli 41001
N. Tekin
Kocaeli University
Turkey
Turkey
Kocaeli 41001
References
1. J. Y. Song, S. H. Jhung, Chem. Eng. J., 322, 366–374 (2017).
2. M. L. Vueba, M. E. Pina, F. Veiga, J. J. Sousa, L. A. E. Batista de Carvalho, Int. J. Pharm., 307, 56–65 (2006).
3. T. Shibata, H. Igawa, T. H. Kim, T. Mori, S. Kojima, J. Mol. Struct., 1062, 185–188 (2014).
4. S. H. Choi, S. Y. Kim, J. J. Ryoo, J. Y. Park, K. P. Lee, Anal. Sci., 17, 785–788 (2001).
5. L. A. E. Batista de Carvalho, M. Paula, M. Marques, J. Tomkinson, Biopolymer, 82, 420–424 (2006).
6. Y. H. Lu, C. B. Ching, Chirality, 16, 541–548 (2004).
7. F. Kayadibi, S. Zor, S. G. Sagdinc, Prot. Met. Phys. Chem. S., 52, 355–370 (2016).
8. M. T. Bilkan, O. Şahin, Ş. Yurdakul, J. Mol. Struct., 1133, 580–590 (2017).
9. T. Polat, G. Yıldırım, Spectrochim. Acta A-M., 123, 98–109 (2014).
10. N. Tekin, H. Pir, S. Sagdinc, Spectrochim. Acta A-M., 98, 122–131 (2012).
11. Y. Chen, H. Zhang, Q. Liu, Spectrochim. Acta A-M., 126, 122–128 (2014).
12. X. Ji, Y. Li, J. Zheng, Q. Liu, Mater. Chem. Phys., 130, 1151–1155 (2011).
13. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 418–424 (2003).
14. M. Tursun, C. Parlak, Spectrochim. Acta A-M., 141, 58–63 (2015).
15. P. Briard, J. Rossi, Acta Crystallogr. C, 46, 1036–1038 (1990).
16. Cambridge Crystallographic DataBase, Cambridge Crystallographic Data Center, Cambridge UK.
17. C. Conti, R. Galeazzi, E. Giorgini, G. Tosi, J. Mol. Struct., 744–747, 417–423 (2005).
18. Q. Liu, C. Cong, H. Zhang, Spectrochim. Acta A, 68, 1269–1273 (2007).
19. S. M. Rafigha, A. V. Yazdia, M. Vossoughib, A. A. Safekordia, M. Ardjmand, Int. J. Biol. Macromol., 70, 463–473 (2014).
Review
For citations:
Sagdinc S., Tekin N. Characterization of solvent effects on C=O stretching vibrations of ketoprofen by empirical solvent parameters. Zhurnal Prikladnoii Spektroskopii. 2021;88(4):663-670.
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