Research Article
Year 2019,
Volume: 6 , 101 - 105, 25.07.2019
Abstract
References
- Bebeda, A.W., van Ree, T. (2015) Conformational performance and electrochemical performance of ethyleneoxy phenyl boronate electrolyte addivites. Arab. J.Sci. Eng 40 28141-2851 Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100 Becke, A. D., 1993. Density-Functional Thermochemistry .3. The Role of Exact Exchange. J. Chem. Phys., 98 (7): 5648-5652 Clapham, K.M., Smith, A.E., Batsanov, A.S., McIntyre, L., Pountney, A ., Bryce, M.R., & Tarbit, B. (2007) 3-New pyrimidylboronic acids and functionalized heteroarylpyrimidines by Suzuki cross-coupling reactions. European Journal Of Organıc Chemıstry 34,5712-5716 Dennington, R., Keith T., Millam, J. (2009). Semichem Inc., GaussView, Version 5, Shawnee Mission KS, Durka, K., Klis, T., & Serwatowski, J. (2014) Crystal structure of (2-benzyloxypyrimidin-5-yl)boronic acid, Acta Cryst. E70, o1259–o1260 Durka, K., Katarzyna Jarzembska., K. N., Kamiński ,R., Luliński, S., Serwatowski, J.,& Woźniak, K., (2012) Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic Acids.Cryst.Growth Des. 12 3720-373 Francl, M.M., Pietro, W.J., Hehre, W.J., Binkley, J.S., Gordon, M.S., DeFrees, D.J., Pople, J.A, (1982). Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements. Chem. Phys, 77 3654-3665 Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida,M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J A, Vreven T J, Peralta J E, Ogliaro F, Bearpark M, Heyd J. J, Brothers E, Kudin N, Staroverov V N, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene,M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C J, Ochterski W, Martin L R, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas O, Foresman J B, Ortiz J V, Cioslowski J, Fox D J, 2009. Gaussian Inc., (Wallingford, CT). Krishnan, R., Binkley, J. S., Seeger, R. and Pople, J. A, (1980). Self-consistent molecular-orbital methods. 20. basis set for correlated wave-functions. J. Chem.Phys, 72: 650–654. Lee, C. T., Yang, W. T., Parr, R. G. (1988). Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785-789. Liao, T. K., Podrebarac, E. G., &Cheng C.C. (1964) Boron-Substituted Pyrimidines J. Am. Chem. Soc.1869-1870 Lulisnki, S., Madura, I., Serwatowski, J., Szatyłowicz, H., & Zachara, J, (2007) A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles New J. Chem., 31, 144-154 Maly, K. E., Maris, T., and Wuest,&J. D. (2006) wo-dimensional hydrogen-bonded networks in crystals of diboronic acids Ctyst Eng Comm. 8, 33-35 McLean, A.D., Chandler, G.S. (1980). Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z= 11–18. J Chem Phys, 72:5639–5648 Moller, C., Plesset, M. S. (1934). Note on an approximation treatment for many- electron systems. Phys. Rev., 46 618-622. Rassolov, V-A., Ratner, M-A., Pople ,J-A., Redfern, P-C., Curtiss ,L-A., (2001). 6–31G* basis set for third-row atoms. J Comp Chem., 22:976–984. Rettig, S.J., Trotte, C.J. (1977) Crystal and molecular structure of phenylboronic acid. Can. J. Chem. Vol. 55. 3071-3075 Saygili, N., Batsanova A. S., &Bryce, M., R. (2004)5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions Organic & Biomolecular Chemistry Issue 6, 852-857 Sowmya, D. V., Teja, G. L., Padmaja, A., Prasad, V. K., Padmavathi, V, (2018) Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity. Eur. J. Med. Chem. 143; 891-898. Wang, B., Qu, Q.T., Xia, Q., Wu, Y.P.,Gan, C.L., van Ree, T. (2008) Effects of 3,5- bis(trifluoromethyl)benzeneboronic acid as an additive on electrochemical performance of propylene carbonate based electrolytes for lithium ion batteries. Electrochim.Acta.54,816-820
Theoretical Studies of the Molecular Structure, Conformational and Nonlinear Optical Properties of (2-Benzyloxy-Pyrimidin-5-Yl) Boronic Acid
Abstract
In
this study, ab initio Hartree-Fock (HF) and Density Functional Theory (DFT),
using Becke-3–Lee–Yang–Parr (B3LYP) hybrid density functional, calculations
have been performed to characterize the ground state geometrical energy, the
dipole moment (μ), polarizability (α), the hyperpolarizability (β) of
(2-benzyloxy-pyrimidin-5-yl) boronic acid molecule. The 1H and 13C
NMR chemical shifts were calculated by GIAO approach by using B3LYP/6-311+G
(2d, p) and HF/6-31G (d) level of theory. The potential energy surface of title
molecule has been investigated as a function dihedral angles (C3-B-O1-H1 and
C3-B-O2-H2). Also, using the calculated
the highest occupied molecular orbital energies (EHOMO) and the
lowest unoccupied molecular orbital energies (ELUMO), electronic
properties of the studied molecules such as energy gap ∆Eg (ELUMO-EHOMO),
chemical potential μ, electrophilic index ω, ionization potential IP, electron
affinity EA, electronegativity χ, molecular softness S, molecular hardness η
were obtained. The dipole moment title molecule are calculated at 1.20 Debye at
DFT/B3LYP/6-311++G (d, p) and 1.58 Debye at HF/6-311++G (d, p), respectively.
Structural parameters of title molecules compared with the experimental data in
the literature. All computational studies have been performed with the Gaussian
09W program.
Keywords
(2-benzyloxy-pyrimidin-5-yl) boronic acid molecule Density functional theory Hyperpolarizability polarizability
References
- Bebeda, A.W., van Ree, T. (2015) Conformational performance and electrochemical performance of ethyleneoxy phenyl boronate electrolyte addivites. Arab. J.Sci. Eng 40 28141-2851 Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100 Becke, A. D., 1993. Density-Functional Thermochemistry .3. The Role of Exact Exchange. J. Chem. Phys., 98 (7): 5648-5652 Clapham, K.M., Smith, A.E., Batsanov, A.S., McIntyre, L., Pountney, A ., Bryce, M.R., & Tarbit, B. (2007) 3-New pyrimidylboronic acids and functionalized heteroarylpyrimidines by Suzuki cross-coupling reactions. European Journal Of Organıc Chemıstry 34,5712-5716 Dennington, R., Keith T., Millam, J. (2009). Semichem Inc., GaussView, Version 5, Shawnee Mission KS, Durka, K., Klis, T., & Serwatowski, J. (2014) Crystal structure of (2-benzyloxypyrimidin-5-yl)boronic acid, Acta Cryst. E70, o1259–o1260 Durka, K., Katarzyna Jarzembska., K. N., Kamiński ,R., Luliński, S., Serwatowski, J.,& Woźniak, K., (2012) Structural and Energetic Landscape of Fluorinated 1,4-Phenylenediboronic Acids.Cryst.Growth Des. 12 3720-373 Francl, M.M., Pietro, W.J., Hehre, W.J., Binkley, J.S., Gordon, M.S., DeFrees, D.J., Pople, J.A, (1982). Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements. Chem. Phys, 77 3654-3665 Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida,M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J A, Vreven T J, Peralta J E, Ogliaro F, Bearpark M, Heyd J. J, Brothers E, Kudin N, Staroverov V N, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene,M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C J, Ochterski W, Martin L R, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas O, Foresman J B, Ortiz J V, Cioslowski J, Fox D J, 2009. Gaussian Inc., (Wallingford, CT). Krishnan, R., Binkley, J. S., Seeger, R. and Pople, J. A, (1980). Self-consistent molecular-orbital methods. 20. basis set for correlated wave-functions. J. Chem.Phys, 72: 650–654. Lee, C. T., Yang, W. T., Parr, R. G. (1988). Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785-789. Liao, T. K., Podrebarac, E. G., &Cheng C.C. (1964) Boron-Substituted Pyrimidines J. Am. Chem. Soc.1869-1870 Lulisnki, S., Madura, I., Serwatowski, J., Szatyłowicz, H., & Zachara, J, (2007) A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles New J. Chem., 31, 144-154 Maly, K. E., Maris, T., and Wuest,&J. D. (2006) wo-dimensional hydrogen-bonded networks in crystals of diboronic acids Ctyst Eng Comm. 8, 33-35 McLean, A.D., Chandler, G.S. (1980). Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z= 11–18. J Chem Phys, 72:5639–5648 Moller, C., Plesset, M. S. (1934). Note on an approximation treatment for many- electron systems. Phys. Rev., 46 618-622. Rassolov, V-A., Ratner, M-A., Pople ,J-A., Redfern, P-C., Curtiss ,L-A., (2001). 6–31G* basis set for third-row atoms. J Comp Chem., 22:976–984. Rettig, S.J., Trotte, C.J. (1977) Crystal and molecular structure of phenylboronic acid. Can. J. Chem. Vol. 55. 3071-3075 Saygili, N., Batsanova A. S., &Bryce, M., R. (2004)5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions Organic & Biomolecular Chemistry Issue 6, 852-857 Sowmya, D. V., Teja, G. L., Padmaja, A., Prasad, V. K., Padmavathi, V, (2018) Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity. Eur. J. Med. Chem. 143; 891-898. Wang, B., Qu, Q.T., Xia, Q., Wu, Y.P.,Gan, C.L., van Ree, T. (2008) Effects of 3,5- bis(trifluoromethyl)benzeneboronic acid as an additive on electrochemical performance of propylene carbonate based electrolytes for lithium ion batteries. Electrochim.Acta.54,816-820
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Details
| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Articles |
| Authors | |
| Publication Date | July 25, 2019 |
| Published in Issue | Year 2019Volume: 6 |
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