Abstract
This research aimed at exploring the stabilities of 2,2-di-tert-butyl-1,3-dioxane, 2,2-di-tert-butyl-1,3-dithian, and 2,2-di-tert-butyl-1,3-diselenan conformers at the B3LYP/6-311+G(d,p) theory level. To this goal, estimations of the total energies, dipole moments, Frontier Orbital Energies (FOEs), and HOMO/LUMO gaps of the chair and twist-boat conformations were first done for the mentioned molecules. The partitioning of the total electronic energy E(tot) into Lewis E(L) and non-Lewis E(NL) parts was performed using the concept of natural bond orbital (NBO) analysis. Then, the Natural Coulomb Electrostatic (NCE) potential energies, total energies into Lewis components, and total steric exchange energies were estimated. Finally, the hyperconjugative anomeric effects on the conformers were illustrated by NBO analysis and the interactions responsible for the effects were explored.
Similar content being viewed by others
REFERENCES
E. L. Eliel, N. L. Allinger, S. J. Angyal, and G. A. Morrisoun Conformarionol Analysis (Interscience, New York 1965).
F. G. Riddell and M. J. T. Robinwn, Tetrahedron 23, 3417 (1967). https://doi.org/10.1016/S0040-4039(00)92651-0
E. J. Corey and D. Seebach, Angew. Chem., Int. Ed. Engl. 4, 1075 (1965). https://doi.org/10.1002/anie.196510752
E. J. Corey and D. Seebach, Angew. Chem., Int. Ed. Engl. 4, 1077 (1965). https://doi.org/10.1002/anie.196510771
P. C. B. Page, M. B. v. Niel, and J. C. Prodger, Tetrahedron 45, 7643 (1989). https://doi.org/10.1016/S0040-4020(01)85784-7
B. T. Grobel and D. Seebach, Synthesis, 6, 357 (1977).https://doi.org/10.1055/s-1977-24412
M. Yus, C. Nájera, and F. Foubelo, Tetrahedron 59, 6147 (2003). https://doi.org/10.1016/S0040-4020(03)00955-4
G. Cuevas and E. Juaristi, J. Am. Chem. Soc. 124, 13088 (2002). https://doi.org/10.1021/ja020317u
I. V. Alabugin, M. Manoharan, and T. A. Zeidan, J. Am. Chem. Soc. 125, 14014 (2003). https://doi.org/10.1021/ja037304g
I. V. Alabugin, J. Org. Chem. 65, 3910 (2000). https://doi.org/10.1021/jo991622+
G. F. Gauze, E. A. Basso, R. H. Contreras, and C. F. Tormena, J. Phys. Chem. A 113, 2647 (2009). https://doi.org/10.1021/jp810981z
E. Juaristi and R. Notario, J. Org. Chem. 83, 3293 (2018). https://doi.org/10.1021/acs.joc.8b00220
O. Y. Kupova, I. V. Vakulin, and R. F. Talipov, Comput. Theor. Chem. 1013, 57 (2013). https://doi.org/10.1016/j.comptc.2013.02.024
V. A. Shiryaev and A. K. Shiryaev, Comput. Theor. Chem. 1044, 87 (2014). https://doi.org/10.1016/j.comptc.2014.06.014
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al.; Revision A.02 ed.; Gaussian, Inc.: Wallingford CT, 2009.
R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, J. Chem. Phys. 72, 650 (1980). https://doi.org/10.1063/1.438955
A. D. McLean and G. S. Chandler, J. Chem. Phys. 72, 5639 (1980). .https://doi.org/10.1063/1.438980
L. A. Curtiss, M. P. McGrath, J.-P. Blandeau, et al., J. Chem. Phys. 103, 6104 (1995). https://doi.org/10.1063/1.470438
A. D. Becke, J. Chem. Phys 98, 5648 (1993). https://doi.org/10.1063/1.464913
K. Fukui, Acc. Chem. Res. 14, 363 (1981). https://doi.org/10.1021/ar00072a001
K. Fukui, J. Phys. Chem. 74, 4161 (1970). https://doi.org/10.1021/j100717a029
C. Gonzalez and H. B. Schlegel, J. Phys. Chem. 94, 5523 (1990). https://doi.org/10.1021/j100377a021
C. Gonzalez and H. B. Schlegel, J. Chem. Phys. 90, 2154 (1989). https://doi.org/10.1063/1.456010
A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev. 88, 899 (1988). https://doi.org/10.1021/cr00088a005
K. B. Wiberg and M. A. Murcko, J. Am. Chem. Soc. 111, 4821 (1989). https://doi.org/10.1021/ja00195a038
K. B. Wiberg and M. A. Murcko, J. Phys. Chem. 91, 3616 (1987). https://doi.org/10.1021/j100297a030
E. Juaristi and G. Cuevas, Tetrahedron 48, 5019 (1992). https://doi.org/10.1016/S0040-4020(01)90118-8
C. L. Perrin, K. B. Armstrong, and M. A. Fabian, J. Am. Chem. Soc. 116, 715 (1994). https://doi.org/10.1021/ja00081a037
M. Wunderlich and F. X. Schmid, Protein Engineering, Design & Selection 19, 355 (2006). https://doi.org/10.1093/protein/gzl019
R. G. Pearson, J. Chem. Educ. 64, 561 (1987). https://doi.org/10.1021/ed064p561
R. G. Parr and P. K. Chattaraj, J. Am. Chem. Soc. 113, 1854 (1991). https://doi.org/10.1021/ja00005a072
R. G. Pearson, Acc. Chem. Res. 26, 250 (1993). https://doi.org/10.1021/ar00029a004
R. G. Pearson, J. Chem. Educ. 76, 267 (1999). https://doi.org/10.1021/ed076p267
P. W. Ayers and R. G. Parr, J. Am. Chem. Soc. 122, 2010 (2000). https://doi.org/10.1021/ja9924039
F. Weinhold, Discovering Chemistry with Natural Bond Orbitals (Wiley, Hoboken, New Jersey, 2012).
C. Romers, C. Altona, H. R. Buys, and E. Havinga, Topics Stereochem. 4, 39 (1969). https://doi.org/10.1002/9780470147139.ch2
S. Wolfe, B. M. Pinto, V. Varma and R. Y. N. Leung, Can. J. Chem. 68, 1051 (1990). https://doi.org/10.1139/v90-164
S. Wolfe and C.-K. Kim, Can. J. Chem. 69, 1408 (1991). https://doi.org/10.1139/v91-208
E. Juaristi and G. Cuevas, Tetrahedron Letters 33, 1847 (1992). https://doi.org/10.1016/S0040-4039(00)74158-X
E. Juaristi, G. Cuevas, and A. Flores-Vela, Tetrahedron Lett. 33, 6927 (1992). https://doi.org/10.1016/S0040-4039(00)60897-3
E. Juaristi, G. Cuevas, and A. Vela, J. Am. Chem. Soc. 116, 5796 (1994). https://doi.org/10.1021/ja00092a034
E. Juaristi, G. Cuevas, and A. Vela, J. Mol. Struct. (Theochem) 418, 231 (1997). https://doi.org/10.1016/S0166-1280(96)05016-6
G. Cuevas, E. Juaristi, and A. Vela, J. Phys. Chem. A 103, 932 (1999). https://doi.org/10.1021/jp983664s
Author information
Authors and Affiliations
Corresponding author
Supplementary material
Rights and permissions
About this article
Cite this article
Morteza Nasrolahi, Ghiasi, R. & Shafiei, F. Theoretical Approaches to the Conformational Preference of 2,2-Di-tert-Butyl-1,3-Dioxane, 2,2-Di-tert-Butyl-1,3-Dithian, and 2,2-Di-tert-Butyl-1,3-Diselenan. Russ. J. Inorg. Chem. 64, 1556–1564 (2019). https://doi.org/10.1134/S0036023619120118
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036023619120118