Abstract
In the present study, siderol acetate (1) was synthesized from siderol isolated from endemic Sideritis species, then its chemical structure was determined by using various spectroscopic methods (FT-IR, 1H NMR, and 13C NMR). The geometrical parameters, vibrational frequencies and gauge including atomic orbital (GIAO) 1H and 13C NMR chemical shift values for siderol acetate in the ground state have been calculated using the Density Functional Theory (DFT) and Hartree–Fock (HF) methods with the 6-31G(d) basis set. The calculated vibrational frequencies and 1H and 13C NMR chemical shifts have been compared with experimental values. A combined study based on NMR data and quantum-mechanical calculations using DFT/GIAO indicate that 1 is the correct structure of the title molecule.
Similar content being viewed by others
REFERENCES
I. Aslan, T. Kılıç, A. C. Gören, and G. Topçu, Ind. Crops Products 23, 171 (2006).
E. González-Burgos, M. E. Carretero, and M. P. Gómez-Serranillos, J. Ethnopharmacol. 135, 209 (2011).
A. Güvenç, Y. Okada, E. Küpeli Akkol, H. Duman, T. Okuyama, and I. Çalıs, Food Chem. 118, 686 (2010).
A. Azizoglu, Z. Özer, and T. Kılıç, Collect. Czech. Chem. Comm. 76, 95 (2011).
T. Wang and X. Wang, Spectrosc. Chim. Acta A 135, 568 (2015).
J. Toušek, S. van Miert, L. Pieters, G. van Baelen, S. Hostyn, B. U. Maes, G. Lemiere, R. Dommisse, and R. Marek, Magn. Reson. Chem. 46, 42 (2008).
O. García-Beltrán, J. Soto-Delgado, P. Iturriaga-Vásquez, C. Areche, and B. K. Cassels, J. Chil. Chem. Soc. 57, 1323 (2012).
L. Gong, W. Fang, F. Liu, X. Shan, L. Sheng, and Z. Wang, J. Electron Spectrosc. Relat. Phenom. 182, 134 (2010).
M. T. Bilkan, Russ. J. Phys. Chem. A 92, 1920 (2018).
T. S. Vishkaee and R. Fazaeli, Russ. J. Phys. Chem. A 92, 1219 (2018).
S. A. Miresmaeili and R. Ghiasi, Russ. J. Phys. Chem. 91, 1026 (2017).
Z. O. Sagir, S. Carikci, T. Kılıç, and A. C. Goren, Int. J. Food Prop. 20, 2994 (2017).
B. M. Fraga, Phytochem. 76, 7 (2012).
G. Topçu, A. Ertas, M. Öztürk, D. Dincel, T. Kılıç, and B. Halfon, Phytochem. Letters 4, 436 (2011).
S. Çarıkçı, Ç. Çöl, T. Kılıç, and A. Azizoglu, Rec. Nat. Prod. 1, 44 (2007).
M. Bruno, F. Piozzi, N. A. Arnold, K. H. C. Başer, N. Tabanca, and N. Kirimer, Turk. J. Chem. 29, 61 (2005).
A. Venditti, A. Bianco, F. Maggi, and M. Nicoletti, Rec. Nat. Prod. 27, 1408 (2013).
T. Kılıç, Molecules 11, 257 (2006).
M. J. Frisch et al., Gaussian 09, Revision A02 (Gaussian Inc., Pittsburgh, PA, 2009).
V. Barone, M. Cossi, and J. Tomasi, J. Comp. Chem. 19, 404 (1998).
I. B. Davydova, S. A. Sharapova, G. M. Kuramshina, and Y. A. Pentin, Russ. J. Phys. Chem. A 89, 1843 (2015).
S. Cıtak, Z. Ozer Sagır, S. Carıkcı, T. Kılıç, and A. Azizoglu, Rev. Roum. Chim. 59, 227 (2014).
G. K. Pierens, J. Comp. Chem. 35, 1388 (2014).
I. Fleming, Frontier Orbitals and Organic Chemical Reactions (Oxford Univ. Press, Oxford, 2010).
L. Găină, I. Torje, E. Gal, A. Lupan, C. Bischin, R. Silaghi-Dumitrescu, G. Damian, P. Lönnecke, C. Cristea, and L. Silaghi-Dumitrescu, Dyes Pigm. 102, 315 (2014).
V. Bucila, M. Stefu, and B. Szefler, Studia UBB Chem. 58, 101 (2013).
V. L. Furer, A. E. Vandyukov, V. Tripathi, J. P. Majoral, A. M. Caminade, and V. I. Kovalenko, J. Mol. Struct. 1162, 1 (2018).
ACKNOWLEDGMENTS
This work was partially supported by University of Balikesir, research grant no. 2017/159.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Züleyha Özer, Kılıç, T., Çarıkçı, S. et al. Synthesis, Structural Characterization, Spectroscopic Properties, and Theoretical Investigation of Siderol Acetate. Russ. J. Phys. Chem. 93, 2703–2709 (2019). https://doi.org/10.1134/S0036024419130235
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024419130235