Interaction of nitronium ion with BN-bond embedded phenanthrenes – A DFT treatment
Abstract
In recent years, boron–nitrogen heteroarenes possess great promise for practical application in many areas of chemistry, biochemistry and pharmacology, beside materials science, and transition-metal-based catalysis. Presently, interaction of B-N bond embedded phenanthrene isomers with the nitronium ion are investigated within the constraints of density functional theory (DFT) at the level of B3LYP/6-31++G(d,p). The collected data have revealed that the optimized structures of them have exothermic heats of formation and favorable Gibbs free energy of formation values. They are thermally favored and electronically stable at the standard states. Various structural and quantum chemical data have been collected and discussed, including bond densities and time dependent density functional UV-VIS spectra.
Downloads
References
Huang, J., & Li, Y. (2018). BN embedded polycyclic π-conjugated systems: Synthesis, optoelectronic properties, and photovoltaic applications. Frontiers in Chemistry, 6, Article 341. https://doi.org/10.3389/fchem.2018.00341
Cid, J., Carbó, J. J., & Fernández, E. (2012). Disclosing the structure/activity correlation in trivalent boron-containing compounds: A tendency map. Chemistry – A European Journal, 18(40), 12794–12802. https://doi.org/10.1002/chem.201200987
Liu, Z.-Q., Fang, Q., Wang, D., Xue, G., Yu, W.-T., Shao, Z.-S., & Jiang, M.-H. (2003). Trivalent boron as acceptor in D–π-A chromophores: Synthesis, structure and fluorescence following single- and two-photon excitation. Chemical Communications, 38(23), 2900–2901. https://doi.org/10.1039/B207210F
Giustra, Z. X., & Liu, S.-Y. (2018). The state of the art in azaborine chemistry: New synthetic methods and applications. Journal of the American Chemical Society, 140(4), 1184–1194. https://doi.org/10.1021/jacs.7b09446
Berionni, G. (2021). Future prospects in boron chemistry: New boron compounds and Lewis acids for catalysis and materials science. Chemical Synthesis, 1(1), Article 10. https://doi.org/10.20517/cs.2021.11
Liu, Z.-Q., Fang, Q., Wang, D., Cao, D.-X., Xue, G., Yu, W.-T., & Lei, H. (2003). Trivalent boron as an acceptor in donor-π-acceptor-type compounds for single- and two-photon excited fluorescence. Chemistry – A European Journal, 9(20), 5074–5084. https://doi.org/10.1002/chem.200304833
Türker, L. (2002). Borazine embedded corannulenes—AM1 treatment. Journal of Molecular Structure: THEOCHEM, 584(1–3), 135–141. https://doi.org/10.1016/S0166-1280(02)00012-X
Türker, L. (2026). A heterofullerene cap having trivalent boron – A DFT treatment. Earthline Journal of Chemical Sciences, 13(1), 87–98. https://doi.org/10.34198/ejcs.13126.07.087098
Edel, K., Yang, X., Ishibashi, J. S. A., Lamm, A. N., Maichle-Mössmer, C., Giustra, Z. X., Liu, S.-Y., & Bettinger, H. F. (2018). The Dewar isomer of 1,2-dihydro-1,2-azaborinines: Isolation, fragmentation, and energy storage. Angewandte Chemie International Edition, 57(19), 5296–5300. https://doi.org/10.1002/anie.201712683
Burford, R. J., Li, B., Vasiliu, M., Dixon, D. A., & Liu, S.-Y. (2015). Diels–Alder reactions of 1,2-azaborines. Angewandte Chemie International Edition, 54(27), 7823–7827. https://doi.org/10.1002/anie.201503483
Stewart, J. J. P. (1989). Optimization of parameters for semi-empirical methods I. Journal of Computational Chemistry, 10(2), 209–220. https://doi.org/10.1002/jcc.540100208
Stewart, J. J. P. (1989). Optimization of parameters for semi-empirical methods II. Journal of Computational Chemistry, 10(2), 221–264. https://doi.org/10.1002/jcc.540100209
Leach, A. R. (1997). Molecular modeling: Principles and applications. Longman.
Kohn, W., & Sham, L. J. (1965). Self-consistent equations including exchange and correlation effects. Physical Review, 140(4A), A1133–A1138. https://doi.org/10.1103/PhysRev.140.A1133
Parr, R. G., & Yang, W. (1989). Density-functional theory of atoms and molecules. Oxford University Press.
Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100. https://doi.org/10.1103/PhysRevA.38.3098
Vosko, S. H., Wilk, L., & Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: A critical analysis. Canadian Journal of Physics, 58(8), 1200–1211. https://doi.org/10.1139/p80-159
Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Physical Review B, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
Wavefunction, Inc. (2006). Spartan’06. Wavefunction, Inc.
Dewar, M. J. S., & Dougherty, R. C. (1975). The PMO theory of organic chemistry. Plenum Press.
Streitwieser, A., Jr. (1961). Molecular orbital theory for organic chemists. John Wiley & Sons.
Türker, L. (2026). Some isomers of BN-embedded phenanthrene – A DFT treatment. Earthline Journal of Chemical Sciences, 13(1), 43–63. https://doi.org/10.34198/ejcs.13126.04.043063
Wavefunction, Inc. (2006). Trident: Molecular modeling for medicinal chemists. Wavefunction, Inc.
Turro, N. J. (1991). Modern molecular photochemistry. University Science Books.
Anslyn, E. V., & Dougherty, D. A. (2006). Modern physical organic chemistry. University Science Books.
Abengózar, A., García-García, P., Fernández-Rodríguez, M. A., Sucunza, D., & Vaquero, J. J. (2021). Recent advances in the chemistry of BN-isosteres of polycyclic aromatic hydrocarbons. In E. F. V. Scriven & C. A. Ramsden (Eds.), Advances in Heterocyclic Chemistry (Vol. 135, pp. 197–275). Academic Press. https://doi.org/10.1016/bs.aihch.2020.10.005
This work is licensed under a Creative Commons Attribution 4.0 International License.
