DFT Investigation of the Structure and Alkaline Earth Cation Selectivity of 1,4-Diazo-2,3,8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione

S. Beshkoofeh; M.A. Safarpour; L. Saranjam; M.T.M. Varnosafadarani

doi:10.14233/ajchem.2013.14264

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Issue Published : May 18, 2013

This work is licensed under a Creative Commons Attribution 4.0 International License.

DFT Investigation of the Structure and Alkaline Earth Cation Selectivity of 1,4-Diazo-2,3,8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione

https://doi.org/10.14233/ajchem.2013.14264

S. Beshkoofeh

College of Chemistry, Iran University of Science and Technology, Tehran, Iran

M.A. Safarpour

College of Chemistry, Iran University of Science and Technology, Tehran, Iran

L. Saranjam

College of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran

M.T.M. Varnosafadarani

College of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran

Corresponding Author(s) : S. Beshkoofeh

sarabeshkoofeh@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 11 (2013): Vol 25 Issue 11
Article Published : June 6, 2013

Abstract

Quantum mechanical study of 1,4-diazo-2,3,8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione and its interaction with the alkaline earth dications Be²⁺, Mg²⁺, Ca²⁺ are presented in this article. This compound is used for the construction of a potentiometric carbon paste modified electrode for calcium ion. All calculation is performed at density functional theory (DFT) level of the theory by using the 6-31G* basis set. Initially the geometry optimizations calculations are accomplished, then frequency and basis set superposition error are performed. The geometric optimization calculations are used to obtain the concerned information of geometric structures of the molecule and the HOMO-LUMO energy gap. The frequency calculations are used to obtain the data of thermo-chemistry such as the complex enthalpy and free Gibbs complex energy formation. Our calculations clearly show that the investigated molecule in fact binds Be²⁺ most strongly in gas phase. Whereas the best selectivity is observed for this molecule in experimental results is Ca²⁺. Thus, solvation effects appear strongly influence cation selectivity.

Keywords

Macrocyclic compound Density functional theory Binding energies

Beshkoofeh, S., Safarpour, M., Saranjam, L., & Varnosafadarani, M. (2013). DFT Investigation of the Structure and Alkaline Earth Cation Selectivity of 1,4-Diazo-2,3,8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione. Asian Journal of Chemistry, 25(11), 6087–6091. https://doi.org/10.14233/ajchem.2013.14264

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References

C.J. Pedersen, Angew. Chem., Int. Ed. Engl., 27, 1021 (1988).

D.J. Cram, Science, 240, 760 (1988).

Y. Tokunaga, T. Nakamura, M. Yoshioka and Y. Shimomura, Tetrahedron Lett., 47, 5901 (2006).

Y. Kuwahara, H. Nagata, H. Nishi, Y. Tanaka and K. Kakehi, Chromatographia, 62, 505 (2005).

M. Mazik, M. Kuschel and W. Sicking, Org. Lett., 8, 855 (2006).

A. Cazacu, C. Tong, A. van der Lee, T.M. Fyles and M. Barboiu, J. Am. Chem. Soc., 128, 9541 (2006).

M. Shamsipour, G. Khayatian and S.Y. Kazemi, J. Incl. Phenom. Macrocycl. Chem., 30, 303 (2001).

V. Arjunan, T. Rani, L. Varalakshmy, S. Mohan and F. Tedlamelekot, Spectrochim. Acta A, 78, 1449 (2011).

C.C. Su, J. Mol. Struct., 888, 33 (2008).

E.D. Glendening, D. Feller and M.A. Thompson, J. Am. Chem. Soc., 118, 6052 (1996).

E.D. Glendening, D. Feller and M.A. Thompson, J. Am. Chem. Soc., 116, 10657 (1994).

J. Korchowiec, B. Korchowiec, W. Priebe and E. Rogalska, J. Phys. Chem. A, 112, 13633 (2008).

C. Platas-Iglesias, D. Esteban-Gomez, T. Enriquez-Peirez, F. Avecilla, A. Blas and T. Rodriguez-Blas, Inorg. Chem., 44, 2224 (2005).

A.D. Becke, J. Chem. Phys., 98, 5648 (1993).

C. Lee, W. Yang and R.G. Parr, Phys. Rev. B., 37, 785 (1988).

P.C. Hariharan and J.A. Pople, Theor. Chim. Acta, 28, 213 (1973).

S.D.M. Chinthaka, Y. Chu, N.S. Rannulu and M.T. Rodgers, J. Phys. Chem. A, 110, 1426 (2006).

I.M. Kenawi, J. Mol. Struct. (Theochem)., 761, 151 (2006).

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J. Garza, J.Z. Ramýrez and R. Vargas, J. Phys. Chem. A, 109, 643 (2005).

J.E. Del Bene, H.D. Mettee, M.J. Frisch, B.T. Luke and J.A. Pople, J. Phys. Chem., 87, 3279 (1983).

J. Casanovas, D. Zanuy and C. Aleman, Macromolecules, 41, 3919 (2008).

U. Salzner, J.B. Lagowski, P.G. Pickup and A. Poirier, J. Comp. Chem., 18, 1943 (1997).

M.A. Safarpour, S.M. Hashemianzadeh and A. Kasaeian, J. Mol. Model., 14, 315 (2008).

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

DFT Investigation of the Structure and Alkaline Earth Cation Selectivity of 1,4-Diazo-2,3,8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione

Corresponding Author(s) : S. Beshkoofeh

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