Document Type : Original Article
Author
Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran
Abstract
In recent years, it has been noted that the silicon analogs compounds have more pharmaceutical applications due to their excellent lipophilicity properties. The present study evaluated the structural, spectral properties, and reactivity of the silicon analogs of cyclobutadiene compound. This study was conducted based on the quantum-mechanical computations. All the studied compounds were optimized by B3LYP/6-311++G(d,p) basis set of theory. The IR computations showed no imaginary frequency for all molecules, proved the accuracy of the methods. The results revealed that, the silicon analogs have more benefits in terms of the structural and stability properties in comparison with the carbon analog.
Graphical Abstract
)
Keywords
Main Subjects
[1]. Kostenko A., Tumanskii B., Kobayashi Y., Nakamoto M., Sekiguchi A., Apeloig Y., Spectroscopic observation of the triplet diradical state of a cyclobutadiene, Angewandte Chemie International Edition, 2017, 56:10183 [Crossref], [Google Scholar], [Publisher]
[2]. Shvydkiy N.V., Perekalin D.S., Cyclobutadiene complexes of platinum metals. Coordination Chemistry Reviews, 2017, 349:156 [Crossref], [Google Scholar], [Publisher]
[3]. Karadakov P.B., Hearnshaw P., Horner K.E., Magnetic shielding, aromaticity, antiaromaticity, and bonding in the low-lying electronic states of benzene and cyclobutadiene, The Journal of Organic Chemistry, 2016, 81:11346 [Crossref], [Google Scholar], [Publisher]
[4]. Han G.D., Collins W.R., Andrew T.L., Bulovic V., Swager T.M., Cyclobutadiene–C60 Adducts: N‐Type Materials for Organic Photovoltaic Cells with High VOC. Advanced functional materials, 2013, 23:3061 [Crossref], [Google Scholar], [Publisher]
[5]. Afanasyev O.L., Tsygankov A.A., Usanov D.L., Perekalin D. ., Shvydkiy N.V., Maleev V.I., Kudinov A.R., Chusov D., Cyclobutadiene metal complexes: a new class of highly selective catalysts. An application to direct reductive amination, ACS Catalysis, 2016, 6:2043 [Crossref], [Google Scholar], [Publisher]
[6]. Wu Y., Liu L., Su J., Zhu J., Ji Z., Zhao Y., Isolation of a heavier cyclobutadiene analogue: 2, 4-digerma-1, 3-diphosphacyclobutadiene. Organometallics, 2016, 35:1593 [Crossref], [Google Scholar], [Publisher]
[7]. Charistos N. D., Papadopoulos A. G., Sigalas M.P., Interpretation of electron delocalization in benzene, cyclobutadiene, and borazine based on visualization of individual molecular orbital contributions to the induced magnetic field. The Journal of Physical Chemistry A, 2014, 118:1113 [Crossref], [Google Scholar], [Publisher]
[8]. Onuma K., Suzuki K., Yamashita M., Rhombic Cyclobutadiene with a Boryl/Amino-Substitution Pattern: Boryl Group Migration Induced by Reaction with Water, Organic letters, 2015, 17:1212 [Crossref], [Google Scholar], [Publisher]
[9]. Perekalin D.S., Shvydkiy N.V., Nelyubina Y.V., Kudinov A.R., General Route to Cyclobutadiene Rhodium Complexes, Chemistry–A European Journal, 2015, 21:16344 [Crossref], [Google Scholar], [Publisher]
[10]. Nabati M., Mahkam M., DFT Study of the Six-Membered Heterocyclic SinN6-nHn (n= 0-6): Stability and Aromaticity, Organic Chemistry Research, 2016, 2:70 [Crossref], [Google Scholar], [Publisher]
[11]. Nabati M., Mahkam M., Synthesis and characterization of novel silyl derivatives of curcumin, Iranian chemical communication, 2014, 2:129 [ [Google Scholar], [Publisher]
[12] Nabati M., Mahkam M., A quantum-mechanical study on nitro and amino derivatives of 1, 2, 3, 4-tetrazine, Journal of Physical and Theoretical Chemistry, 2015, 12:121 [Google Scholar], [Publisher]
[13]. Nabati M., A quantum-mechanical investigation of functional group effect on 5, 5'-disubstituted-1, 1'-azobis (tetrazoles), Journal of Physical and theoretical Chemistry, IAU Iran, 2015, 12:325 [Google Scholar], [Publisher]
[14]. Nabati M., Prediction of the structural and spectral properties for L, L-ethylenedicysteine diethylester (EC) and its complex with Technetium-99m radionuclide, Journal of Physical & Theoretical Chemistry, 2017, 14:49 [Google Scholar], [Publisher]
[15]. Nabati M., Mahkam M., DFT Study of 1H-tetrazolyl derivatives of tetrahedrane, Journal of Physical & Theoretical Chemistry, 2015, 12:33 [Google Scholar], [Publisher]
[16]. Nabati M., Mahkam M., Gholizade, A.Y., Theoretical study of tetrahedrane derivatives, Journal of Physical & Theoretical Chemistry, 2016, 13:35 [Google Scholar], [Publisher]
[17]. Nabati M., Density functional theory study of the structural properties of cis-trans isomers of bis-(5-nitro-2H-tetrazolato-N2) tetraammine cobalt (III) perchlorate (BNCP), Journal of Physical & Theoretical Chemistry, 2016, 13:133 [Google Scholar], [Publisher]
[18]. Nabati M., Mahkam M., Natural Bond Orbital (NBO) Study of (5H-tetrazol-1-yl)(triphenylphosphine) gold [Au (tetz)(PPh3)]. Inorganic Chemistry Research, 2016, 1:131 [Crossref], [Google Scholar], [Publisher]
[19]. Nabati M., Mahkam M., Computational Study of Octasilacubane Structural Properties with Density Functional Theory Method, Silicon, 2016, 8:461 [Crossref], [Google Scholar], [Publisher]
[20]. Nabati M., Mahkam M., Density functional theory study of molecular structure, chemical reactivity and radical scavenging potency of (+)-curcutetraol, Iranian Journal of Organic Chemistry, 2015, 7:1631 [Google Scholar], [Publisher]
[21]. Nabati M., 1, 3, 4-Thiadiazole rings as π-spacers in triphenylamine based dyes: A density functional theory study of reactivity, UV/Visible spectra, structural and optical properties. Iranian Journal of Organic Chemistry, 2015, 7:1669 [Google Scholar], [Publisher]
[22]. Nabati M., A DFT treatment on nitro derivatives of pyrazine, Iranian Journal of Organic Chemistry, 2016, 8:1703 [Google Scholar], [Publisher]
[23]. Nabati M., Hojjati M., Structural and energetically study on nitro and amino derivatives of 1, 2, 3, 5-
Tetrazine, Iranian Journal of Organic Chemistry, 2016, 8:1777 [Publisher]
[24]. Nabati M., A computational study on the 5-substituted 1H-tetrazoles: Structure, stability and aromaticity, Iranian Journal of Organic Chemistry, 2016, 8:1803 [Google Scholar], [Publisher]
[25]. Nabati M., DFT investigation of 1, 1'-disubstituted-5, 5'-azotetrazoles: a study of functional group effect, Iranian Journal of Organic Chemistry, 2016, 8:1817 [Google Scholar], [Publisher]
[26]. Nabati M., Quantum-chemical study of stability, aromaticity and reactivity properties on O-and S-heterocyclic divalent five-memberedRings C2H2X2M (X= O and S; M= C, Si, Ge, Sn and Pb), Iranian Journal of Organic Chemistry, 2016, 8:1935 [Google Scholar], [Publisher]
[27]. Nabati M., Quantum-mechanical investigation of 1-benzyl-1, 4, 7, 10-tetraazacyclododecane: a density functional theory (DFT) treatment, Iranian Journal of Organic Chemistry, 2017, 9:2045 [Google Scholar], [Publisher]
[28]. Nabati M., Salehi H., Theoretical investigation on the H and 13 C chemical shifts of TRODAT-1 compound with density functional theory and Hartree-Fock computational methods, Iranian Journal of Organic Chemistry, 2017, 9:2013 [Google Scholar], [Publisher]
[29]. Nabati M., Mofrad M.H., Kermanian M., Sarshar S., Theoretical studies on the structural properties, aromaticity and reactivity of 1H-phosphole derivatives, Iranian Journal of Organic Chemistry, 2017, 9:1981 [Publisher]
[30]. Nabati M., Kermanian M., Maghsoudloo-Mahalli A., Sarshar S., DFT study of [18F]flubatine, Iranian Journal of Organic Chemistry, 2017, 9:2067 [Publisher]
)
