Chemical Review and Letters

Investigation of Ti—B nanoheterofullerenes evolved from C20 nanocage through DFT

Document Type : Research Article

Authors

Maryam Koohi 1
Hajieh Bastami 2

1 Department of chemistry, Technical and Vocational University (TVU), Tehran, Iran

2 Department of materials and Metallurgical Engineering, Technical and Vocational University (TVU), Tehran, Iran

https://doi.org/10.22034/crl.2023.392356.1222
Abstract
In present computational survey, we are compared and contrasted electronic effects of C20 and its C20-2nTinBn heterofullerenic derivatives with n = 1-5, at density functional theory (DFT). All nanocages are true minima and none of them collapses to deformed open cage as segregated nanostructure. Isolating five single hetero bonds of Ti—B via either one double bond of C═C or one carbon atom is a suitable method for reaching highly substituted stable heterofullerene i.e. pen-shell C10Ti5B5 since it prevents from weak homo bonding of Ti—Ti and B—B. The C1-C18Ti1B1 heterofullerene can avoid from the most strained directly fused five-pentagon configuration, but its open-shell electronic structure with highly pyramidalized titanium atom (126.59° i.e. 3-4 times relation to C20) may render it too reactive to be observed under typical experimental conditions. The calculated binding energy (B.E.) shows C10Ti5B5 as the most stable heterofullerene. Contrary on B.E., the absolute heat of atomization of heterofullerenes decreases as number of substituting Ti―B unit (n) increases. Hence, substitution effect on binding energy is more significant than heat of atomization. Compared to the previously reported material such Ti-decorated B38 nanofullerene as a suitable hydrogen storage with B.E. of 5.67 eV/atom, our studied C20-2nTinBn heterofullerenes show the higher B.E. with range of 12.25 to 38.03 eV/atom, the higher stability and the higher capacity for hydrogen storage. Interestingly, C18Ti1B1 heterofullerene must be not only kinetically stable against electronic excitations but also based on natural bond orbital (NBO) analysis, the highest charge transfer (CT) is take placed from πC=C bonds to the neighboring LP*B, LP*Ti and σ*Ti-B anti-bonds of it. Also, the exceptionally large value of nucleus-independent chemical shifts (NICS) is found for C18Ti1B1 compared to the archetypically aromatic benzene and [2.2]paracyclophane molecules.

Keywords

C20-2nTinBn
Heterofullerene
Substituent effect
Stability

Subjects

  1. (a) T. M. Simeon, I. Yanov, J. Leszczynski, Ab initio quantum chemical studies of fullerene molecules with substitutes C59 [X = Si, Ge, Sn], C59X− [X = B, Al, Ga, In], and C59X+ [X = N, P, As, Sb]. Int. J. Quantum. Chem. 105 (2005) 429. (b) Z. Chen, R. B. King, Spherical aromaticity: recent work on fullerenes, polyhedral boranes, and related structures. Chem. Rev. 105 (2005) 3613. (c) O. Vostrowsky, A. Hirsch, Heterofullerenes. Chem. Rev. 106 (2006) 5191. (d) I. Zanella, A. Fazzio, A. J. R. da Silva, C59Si on the Monohydride Si (100): H−(2× 1) Surface. J. Phys. Chem. B 110 (2006) 10849. (e) C. Massobrio, D. M. Djimbi, M. Matsubara, R. Scipioni, M. Boero, Stability of Ge12C48 and Ge20C40 heterofullerenes: A first principles molecular dynamics study. Chem. Phys. Lett. 556 (2013) 163. (f) L. Koponen, M. J. Puska, R. M. Nieminen, Photoabsorption spectra of small fullerenes and Si-heterofullerenes. J Chem Phys 128 (2008) 154307.
  2. (a) Akasaka, F. Wudl, S. Nagase, Chemistry of Nanocarbons. Angew. Chem. Int. Ed. 50 (2011) 4048. (b) O. Vostrowsky, A. Hirsch, Heterofullerenes. Chem. Rev. 106 (2006) 5191. (c) N. Lou, Y. Li, C. Cui, Y. Liu, L. Gan, Preparation of Azafullerene C59NR5 and Fullerene Derivative C60NAr5 with a Pyridine Moiety on the Cage Skeleton. Org. Lett. 18 (2016) 2236. (d) Y. Hashikawa, M. Murata, A. Wakamiya, Y. Murata, Synthesis and Properties of Endohedral Aza[60]fullerenes: H2O@C59N and H2@C59N as Their Dimers and Monomers. J. Am. Chem. Soc. 138 (2016) 4096. (e) L. Martín-Gomis, G. Rotas, K. Ohkubo, F. Fernández-Lázaro, S. Fukuzumi, N. Tagmatarchis, Á. Sastre-Santos, Does a nitrogen matter? Synthesis and photoinduced electron transfer of perylenediimide donors covalently linked to C59N and C60 acceptors. Nanoscale 7 (2015) 7437. (f) W. Cambarau, U. F. Fritze, A. Viterisi, E. Palomares, M. von Delius, Increased short circuit current in an azafullerene-based organic solar cell. Chem Commun 51 (2015) 1128. (g) C. D. Wessendorf, R. Eigler, S. Eigler, J. Hanisch, A. Hirsch, E. Ahlswede, Investigation of pentaarylazafullerenes as acceptor systems for bulk-heterojunction organic solar cells. Sol. Energy Mater. Sol. Cells 132 (2015) 450.
  3. (a) K. S. Novoselov, A. K. Geim, S. V. Morozov, D. Jiang, Y. Zhang, S. V. Dubonos, I. V. Grigorieva, A. A. Firsov, Electric field effect in atomically thin carbon films. Science 306 (5696) (2004) 666. (b) H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, R. E. Smalley, C60: Buckminsterfullerene. Nature 318 (1985) 162. (c) A. Mujica, A. Rubio, A. Munoz, R. J. Needs, High-pressure phases of group IV, III–V, and II–VI compounds. Rev. Mod. Phys. 75 (2003) 863. (d) W. J. Chao, R. Kosugi, J. Senzaki, K. Fukuda, K. Arai, S. Suzuki, New High-k SrTa2O6 Gate Dielectrics Prepared by Plasma-Enhanced Atomic Layer Chemical Vapor Deposition. Appl. Phys. Lett. 77 (2000) 2054. (e) P. Schwerdtfeger, L. N. Wirz, J. Avery, The topology of fullerenes. WIREs Comput. Mol. Sci. 5 (2015) 96. (f) X. Lu, Z. Chen, Curved π-conjugation, aromaticity, and the related chemistry of small fullerenes (< C60) and single-walled carbon nanotubes. Chem. Rev. 105 (2005) 3643.
  4. (a) H. Dong, T. Hou, S. T. Lee, Y. Y. Li, New Ti-decorated B40 fullerene as a promising hydrogen storage material, Sci. Rep. 5 (2015) 9952. (b) Q. L. Lu, S. G. Huang, Y. D. Li, J. G. Wan, Q. Q. Luo, Alkali and alkalineearth atom-decorated B38 fullerenes and their potential for hydrogen storage. Int. J. Hydrogen Energy 40(38) (2015) 13022. (c) N. G. Szwacki, A. Sadrzadeh, B. I. Yakobson, B80 fullerene: an ab initio prediction of geometry, stability, and electronic structure. Phys. Rev. Lett. 98 (2007) 166804. (d) C. Özdogan, S. Mukhopadhyay, W. Hayami, Z. B. Güvenc, R. Pandey, I. Boustani, The unusually stable B100 fullerene, structural transitions in boron nanostructures, and a comparative study of a-and g-boron and sheets. J. Phys. Chem. C 114 (2010) 4362. (e) Q. B. Yan, X. L. Sheng, Q. R. Zheng, L. Z. Zhang, G. Su, Family of boron fullerenes: general constructing schemes, electron counting rule, and ab initio Phys. Rev. B 78 (2008) 201401.
  5. (a) J. T. Muya, G. Gopakumar, M. T. Nguyen, A. Ceulemans, The leapfrog principle for boron fullerenes: a theoretical study of structures and stability of B112. Phys. Chem. Chem. Phys. 13 (2011) 7524. (b) T. BaáTai, M. ThoáNguyen, A new chiral boron cluster B44 containing nonagonal holes. Chem. Commun. 52 (2016) 1653. (c) Y. J. Wang, Y. F. Zhao, W. L. Li, T. Jian, Q. Chen, X. R. You, T. Ou, X. Y. Zhao, H. J. Zhai, S. D. Li, J. Li, L. S. Wang, Observation and characterization of the smallest borospherene. B28- and B28. J. Chem. Phys. 144 (2016) 064307. (d) N. G. Szwacki, Boron fullerenes: a first-principles study. Nanoscale Res. Lett. 3 (2008) 49. (e) X. L. Sheng, Q. B. Yan, Q. R. Zheng, G. Su, Boron fullerenes B32‏ 8k with four-membered rings and B32 solid phases: geometrical structures and electronic properties. Chem. Chem. Phys. 11 (2009) 9696.
  6. (a) L. Wang, J. Zhao, F. Li, Z. F. Chen, Boron fullerenes with 32-56 atoms: irregular cage configurations and electronic properties. Chem. Phys. Lett. 501 (2010) 16. (b) R. R. Zope, T. Baruah, K. C. Lau, A. Y. Liu, M. R. Pederson, B. I. Dunlap, Boron fullerenes: from B80 to hole doped boron sheets. Phys. Rev. B 79 (2009) 161403. (c) Y. Li, G. Zhou, J. Li, B. L. Gu, W. H. Duan, Alkali-metal-doped B80 as high-capacity hydrogen storage media. J. Phys. Chem. C 112 (2008) 19268. (d) M. Li, Y. Li, Z. Zhou, P. Shen, Z. Chen, Ca-coated boron fullerenes and nanotubes as superior hydrogen storage materials. Nano Lett. 9 (2009) 1944. (e) Y. F. Zhao, M. T. Lusk, A. C. Dillon, M. J. Heben, S. B. Zhang, Boronbased organometallic nanostructures: hydrogen storage properties and structure stability. Nano Lett. 8 (2008) 157. (f) J. L. Li, Z. S. Hu, G. W. Yang, High-capacity hydrogen storage of magnesium-decorated boron fullerene. Chem. Phys. 392 (2012) 16.
  7. (a) W. W. Wu, Z. Y. Tian, S. L. Dong, Yttrium-dispersed B80 fullerenes: promising materials for hydrogen storage. Eur. Phys. J. 109 (2015) 56004. (b) G. Wu, J. Wang, X. Zhang, L. Zhu, Hydrogen storage on metalcoated B80 buckyballs with density functional theory. J. Phys. Chem. C 113 (2009) 7052. (c) E. Durgun, S. Ciraci, W. Zhou, T. Yildirim, Transition-metalethylene complexes as high-capacity hydrogen-storage media. Phys. Rev. Lett. 97 (2006) 226102. (d) A. S. Shalabi, S. A. Aal, M. M. Assem, W. S. Abdel Halim, Ab initio characterization of Ti decorated SWCNT for hydrogen storage. Int. J. Hydrogen Energy 38 (2013) 140.
  8. (a) S. Barman, P. Sen, G. P. Das, Ti-decorated doped silicon fullerene: a possible hydrogen-storage material. J. Phys. Chem. C 112 (2008) 19963. (b) Q. X. Bao, H. Zhang, S. W. Gao, X. D. Li, X. L. Cheng, Hydrogen adsorption on Ti containing organometallic structures grafted on silsesquioxanes. Struct. Chem. 21 (2010) 1111. (c) C. Tang, S. Chen, W. Zhu, J. Kang, X. He, Z. J. Zhang, Transition metal Ti coated porous fullerene C24B24: potential material for hydrogen storage. Int. J. Hydrogen Energy 40 (2015) 16271. (d) A. Lebon, J. Carrete, L. J. Gallego, A. Vega, Ti-decorated zigzag graphene nanoribbons for hydrogen storage. A van der Waals-corrected density-functional study. Int. J. Hydrogen Energy 40 (2015) 4960. (e) Q. Sun, Q. Wang, P. Jena, Y. Kawazoe, Clustering of Ti on a C60 surface and its effect on hydrogen storage. J Am Chem Soc 127 (2005) 14582.
  9. (a) Koohi, S. Soleimani-Amiri, M. Shariati, Novel X- and Y-substituted heterofullerenes X4Y4C12 developed from the nanocage C20, where X = B, Al, Ga, Si and Y = N, P, As, Ge: a comparative investigation on their structural, stability, and electronic properties at DFT. Struct. Chem. 29(3) (2018) 909. (b) M. T. Baei, M. Koohi, M. Shariati, Characterization of C20 fullerene and its isolated C20-nGen derivatives (n = 1-5) by alternating germanium atom(s) in equatorial position: A DFT survey. Heteroatom Chem. 29 (2018) e21410. (c) M. T. Baei, M. Koohi, M. Shariati, Structure, stability, and electronic properties of AlP nanocages evolved from the world's smallest caged fullerene C20: A computational study at DFT. J. Mol. Struct. 1159 (2018) 118. (d) S. Soleimani Amiri, M. Koohi, B. Mirza, Characterizations of B, and N heteroatoms as substitutional doping on structure, stability, and aromaticity of novel heterofullerenesevolvedfrom the smallest fullerene cage C20: A density functional theory perspective. J. Phys. Org. Chem. 29 (2016) 514. (e) M. Koohi, S. Soleimani Amiri, B. N. Haerizade, Substituent effect on structure, stability and aromaticity of novel BnNmC20-(n+m) heterofullerenes. J. Phys. Org. Chem. 30 (2017) e3682. (f) M. Koohi, M. Z. Kassaee, M. Ghavami, B. N. Haerizade, A. A. Ahmadi, C20-nGen heterofullerenes (n = 5 - 10) on focus: a density functional perspective. Monatsh. Chem. 146 (2015) 1409. (g) M. Koohi, S. Soleimani Amiri, M. Shariati, Silicon impacts on structure, stability and aromaticity of C20-nSin heterofullerenes (n = 1 - 10): a density functional perspective. J. Mol. Struct. 1127 (2017) 522. (h) M. Koohi, M. Shariati, S. Soleimani Amiri, A comparative study on the Ge6C14 heterofullerene nanocages: a density functional survey. J. Phys. Org. Chem. 30 (2017) e3678. (i) S. Soleimani-Amiri, M. Koohi, Z. Azizi, Characterization of nonsegregated C17Si3 heterofullerenic isomers using density functional theory method. J Chin Chem Soc 65 (2018) 1453.
  10. (a) R. Tawfeeq Kareem, Z. Rahmani, S. Ebrahimiasl, A. Ebadi, Z. Rostami Characterization of titanium influences on structure and thermodynamic stability of novel C20-nTin nanofullerenes (n = 1 - 5): A density functional perspective. J. Mol. Model. 27(6) (2021) 176. (b) T. Kareem, S. Ahmadi, Z. Rahmani, A. G. Ebadi, S. Ebrahimiasl, Characterization of titanium influences on structure and thermodynamic stability of novel C20-nTin nanofullerenes (n=1-5): a density functional perspective. J. Mol. Model. 27(6) (2021) 176. (c) E. Vessally, M. D. Esrafili, R. Nurazar, P. Nematollahi, A. Bekhradnia, A DFT study on electronic and optical properties of aspirin–functionalized B12N12 fullerene–like nanocluster. Struct. Chem. 28 (2017) 735. (d) E. Vessally, E. Ahmadi, S. Alibabaei, M. D. Esrafili, A.Hosseinian, Adsorption and decomposition of formaldehyde on the B12N12 nanostructure: a density functional theory study. Monatsh. Chem. 148 (2017) 1727.
  11. (a) S. A. Siadati, E. Vessally, A. Hosseinian, L. Edjlali, Possibility of sensing, adsorbing, and destructing the Tabun–2D–skeletal (Tabun nerve agent) by C20 fullerene and its boron and nitrogen doped derivatives. Synthetic Met 220 (2016) 606. (b) E. Vessally, S. A. Siadati, A. Hosseinian, L. Edjlali, Selective sensing of ozone and the chemically active gaseous species of the troposphere by using the C20 fullerene and graphene segment. Talanta 162 (2017) 505. (c) E. Vessally, S. Soleimani–Amiri, A. Hosseinian, L. Edjlali, A. Bekhradnia, The Hartree–Fock exchange effect on the CO adsorption by the boron nitride nanocage. Physica E 87 (2017) 308. (d) K. Nejati, A. Hosseinian, E. Vessally, A. Bekhradnia, L. Edjlali, A comparative DFT study on the interaction of cathinone drug with BN nanotubes, nanocages, and nanosheets. Appl. Surf. Sci. 422 (2017) 763. (e) A. Hosseinian, E. Vessally, A. Bekhradnia, K. Nejati, G. Rahimpour, Benzoylethanamine drug interaction with the AlN nanosheet, nanotube and nanocage: Density functional theory studies. Thin Solid Films 640 (2017) 93.
  12. (a) A. Hosseinian, A. Bekhradnia, E. Vessally, L. Edjlali, M. D. Esrafili, A DFT study on the central–ring doped HBC nanographenes. J. Mol. Graph. Model. 73 (2017) 101. (b) A. Hosseinian, Z. Asadi, L. Edjlali, A. Bekhradnia, E. Vessally, NO2 sensing properties of a borazine doped nanographene: A DFT study. Comput. Theor. Chem. 1106 (2017) 36. (c) K. Nejati, A. Hosseinian, A. Bekhradnia, E. Vessally, L. Edjlali, Na–ion batteries based on the inorganic BN nanocluster anodes: DFT studies. J. Mol. Graph. Model. 74 (2017) 1. (d) B. Mirza, S. Soleimani-Amiri, M. Mirza, Reaching for [6]n SiC-cyclacenes and [6]n SiC-acenes: A DFT approach. J. Phys. Org. Chem. 31 (2017) 3754. (e) E. Vessally, S. Soleimani–Amiri, A. Hosseinian, L. Edjlali, A. Bekhradnia, A comparative computational study on the BN ring doped nanographenes. Appl. Surf. Sci. 396 (2017) 740. (f) K. Nejati, A. Hosseinian, L. Edjlali, E. Vessally, The effect of structural curvature on the cell voltage of BN nanotube based Na–ion batteries. J. Mol. Liq. 229 (2017) 167. (g) Safari, E. Vessally, A. Bekhradnia, A. Hosseinian, L. Edjlali, A DFT study on the sensitivity of two–dimensional BN nanosheet to nerve agents cyclosarin and tabun. Thin Solid Films, 623 (2017) 157. (d) M. Koohi, H. Bastami, Structure, stability, MEP, NICS, reactivity, and NBO of Si—Ge nanocages evolved from C20 fullerene at DFT. Monatshefte für Chemie – Chem. Mont. 151 (2020) 693.
  13. (a) E. Vessally, F. Behmagham, B. Massoumi, A. Hosseinian, L. Edjlali, Carbon nanocone as an electronic sensor for HCl gas: Quantum chemical analysis. Vacuum, 134 (2016) 40. (b) S. Bashiri, E. Vessally, A. Bekhradnia, A. Hosseinian, L. Edjlali, Utility of extrinsic [60] fullerenes as work function type sensors for amphetamine drug detection: DFT studies. Vacuum, 136 (2017) 156. (c) F. Behmagham, E. Vessally, B. Massoumi, A. Hosseinian, L. Edjlali, A computational study on the SO2 adsorption by the pristine, Al, and Si doped BN nanosheets, Superlattices Microstruct. 100 (2016) 350. (d) M. Koohi, M. Ghavami, B. N. Haerizade, H. Zandi, M. Z. Kassaee, Cyclacenes and short zigzag nanotubes with alternanting Ge―C bonds: theoretical impacts of Ge on the ground state, strain, and band gap. J. Phys. Org. Chem. 27 (2014) 735.
  14. (a) A. D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A 38 (1988) 3098. (b) A. D. J. Becke, Density‐functional thermochemistry. III. The role of exact exchange, Chem. Phys. 98 (1993) 5648. (c) C. Lee, W. Yang, R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37 (1988) 785. (d) A. D. Becke, Density‐functional thermochemistry. IV. A new dynamical correlation functional and implications for exact‐exchange mixing, J. Chem. Phys. 104 (1996) 1040.
  15. (a) M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, General atomic and molecular electronic structure system, J. Comput. Chem., 14 (11) (1993) 1347. (b) A. L. Sobolewski, W. Domcke, Ab Initio Investigation of the Structure and Spectroscopy of Hydronium−Water Clusters, J. Phys. Chem. A 106 (2002) 4158.
  16. Zhao, D. G. Truhlar, The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals, Theor. Chem. Account. 120 (2008) 215.
  17. (a) J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York (1986). (b) J. B. Foresman, A. Frisch, Exploring Chemistry with Electronic structure Methods, Gaussian, Inc., Pittsburgh. PA (1996). (c) P. C. Hariharan, J. A. Pople, Accuracy of AH, equilibrium geometries by single determinant molecular orbital theory. J. Mod. Phys. 27 (1974) 209. (d) M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, Self-Consistent Molecular Orbital Methods. XXIII. A Polarization-Type Basis Set for Second Row Elements, J. Chem. Phys. 77 (1982) 3654. (e) M. J. Frisch, J. A. Pople, J. S. Binkley, Self-Consistent Molecular Orbital Methods 25: Supplementary Functions for Gaussian Basis Sets, J. Chem. Phys. 80 (1984) 3265. (f) T. Clark, J. Chandrasekhar, G. W. Spitznagel, P.v.R. Schleyer, Efficient diffuse function-augmented basis sets for Anion Calculations. III. The 3-21+G set for first-row elements, Li-F, J. Comput. Chem. 4 (1983) 294.
  18. (a) F. Weinhold, E. D. Glendening, NBO 7.0 Program Manual Natural Bond Orbital Analysis Programs. Comput. Chem. 33 (2012) 2363. (b) F. Weinhold, Natural Bond Orbital Analysis: A Critical Overview of Relationships to Alternative Bonding Perspectives. J. Comput. Chem. 33 (2012) 2363. (c) E. D. Glendening, C. R. Landis, F. Weinhold, Natural bond orbital methods. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2 (2012) 1. (d) G. Zhang, C. B. Musgrave, Comparison of DFT Methods for Molecular Orbital Eigenvalue Calculations. J. Phys. Chem. A 111 (2007) 1554.
  19. (a) Krishna, M. J. Frisch, J. A. Pople, Contribution of Triple Substitutions to the Electron Correlation Energy in Fourth Order Perturbation Theory. J. Chem. Phys. 72 (1980) 4244. (b) R. A. Kendall, T. H. Jr. Dunning, R. J. Harrison, Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions. J. Chem. Phys. 96 (1992) 6796. (c) J. P. Predew, Y. Wang, Accurate and simple analytic representation of the electron-gas correlation energy. Phys. Rev. B 45 (1992) 13244.
  20. (a) v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, Nucleus-independent chemical shifts (NICS): a simple and efficient aromaticity probe. J. Am. Chem. Soc. 118 (1996) 6317. (b) P. v. R. Schleyer, H. Jiao, N. J. R. van Eikema Hommes, V. G. Malkin, O. L. Malkina, An evolution of the aromaticity of inorganic rings: refined evidence from magnetic properties. J Am Chem Soc 119 (1997) 12669. (c) P. v. R. Schleyer, M. Manoharan, Z. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van Eikema Hommes, Dissected nucleus-independent chemical shift analysis of p-aromaticity and antiaromaticity. Org. Lett. 3(16) (2001) 2465.
  21. (a) M. R. Ibrahim, P. v. R. Schleyer, Atom Equivalents for Relating Ab Initio Energies to Enthalpies of Formation. J. Comput. Chem. 6 (1985) (b) N. Mizorogi, J.-I. Aihara, PM3 localization energies for the isolated-pentagon isomers of the C84 fullerene. Phys. Chem. Chem. Phys. 5 (2003) 3368. (c) M. Watanabe, D. Ishimaru, N. Mizorogi, M. Kiuchi, J.-I. Aihara, Thermodynamically and kinetically stable isomers of the C88 and C90 fullerenes. J. Mol. Struct. (THEOCHEM) 726 (2005) 11. (d) Z. Yang, X. Xu, G. Wang, Z. Shang, Z. Cai, Y. Pan, X. Zhao, A systematic investigation on the molecular behaviors of substituted fullerenes C34X2 (X = N, B). J. Mol. Struct. (THEOCHEM) 618 (2002) 191.
  22. (a) R. Domingo, E. Chamorro, P. Pérez, Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study. J Org Chem 73 (2008) 4615. (b) R. G. Parr, L. Szentpaly, S. Liu, Electrophilicity Index. J. Am. Chem. Soc. 121 (1999) 1922. (c) R. G. Pearson Absolute electronegativity and hardness: applications to organic chemistry. J. Org. Chem. 54 (1989) 1423. (d) P. K. Chattaraj, S. Giri, Stability, Reactivity, and Aromaticity of Compounds of a Multivalent Superatom. J. Phys. Chem. A 111 (2007) 11116. (e) J. Padmanabhan, R. Parthasarathi, V. Subramanian, P. K. Chattaraj, Electrophilicity-Based Charge Transfer Descriptor. J. Phys. Chem. A 111 (2007) 1358.
  23. (a) R. C. Haddon, L. T. Scott, π-Orbital Conjugation and Rehybridization in Bridged Annulenes and Deformed Molecules in General: π-Orbital Axis Vector Analysis. Pure Appl. Chem. 58 (1986) 137. (b) R. C. Haddon, Chemistry of the fullerenes: The manifestation of strain in a class of continuous aromatic molecules. Science 261 (1993) 1545. (c) T. Lin, W.-D. Zhang, J. Huang, C. He, A DFT Study of the Amination of Fullerenes and Carbon Nanotubes:  Reactivity and Curvature. Phys. Chem. B 109 (2005) 13755. (d) H. Prinzbach, A. Weller, P. Landenberger, F. Wahl, J. Worth, L. T. Scott, M. Gelmont, D. Olevano, B. Issendorff, Gas-Phase Production and Photoelectron Spectroscopy of the Smallest Fullerene, C20. Nature 407 (2000) 60. (e) Z. Chen, T. Heine, H. Jiao, A. Hirsch, W. Thiel, P. v. R. Schleyer, Theoretical Studies on the Smallest Fullerene: From Monomer to Oligomers and Solid States. Chem. Eur. J. 10 (2004) 963. (f) A. Hirsch, Z. Chen, H. Jiao, Spherical Aromaticity in Ih Symmetrical Fullerenes: The 2(N+1)2 Rule. Angew. Chem. Int. Ed. 39 (2000) 3915–3917. (g) M. N. Huda, A. K. Ray, Evolution of SiC nanocluster from carbon fullerene, a density functional theoretic study. Chem. Phys. Lett. 457 (2008) 124. (h) R. W. Alder, M. E. Blake, J. M. Oliva, Diaminocarbenes; Calculation of Barriers to Rotation about Ccarbene-N Bonds, Barriers to Dimerization, Proton Affinities and 13C NMR Shifts. J. Phys. Chem. A 103 (1999) 11200.
  24. Hoffmann, P. v. R. Schleyer, H. F. Schaefer, Predicting Molecules—More Realism, Please!. Angew. Chem. Int. Ed. 47 (2008) 7164.
Chemical Review and Letters
Volume 6, Issue 2 - Serial Number 2
Summer 2023
Pages 223-234

  • Receive Date 08 April 2023
  • Revise Date 21 July 2023
  • Accept Date 25 July 2023

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