Synthesis and unusual electrochemical properties of nitropyrimidine-substituted diazadihomo(C60-Ih)[6,6]fullerene

Romanova, I. P.; Yusupova, G. G.; Larionova, O. A.; Nafikova, A. A.; Yakhvarov, Dmitry G.; Зверев, В. В.; Efremov, Yury Ya.; Sinyashin, Оleg G.

doi:10.1070/mc2006v016n06abeh002387

Cited by 7 publications

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References 16 publications

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“…The EA values, scaled by the experimental value of the fulleren C 60 EA (2.650 eV), are obtained from the energies of the low virtual orbital, calculated by the DFT/PBE method. Electrochemical researches also testify to substantial growth of EA of homodiazafullerene 13 [20]. Comparison of the reduction potentials for bis-adduct 13 and pristine C 60 demonstrates that the first reduction peak of the fullerene sphere of 13 is shifted by 230 mV to the anode region.…”

Section: Valence Isomersmentioning

confidence: 97%

“…For the compound 8 the closed form is considerably, by 5.94 kcal/mol, more stable than the open form, for compounds 13,14 on the contrary, the open form is much more stable than the closed one, by 4.11 and 1.92 kcal/mol. This is coordinated to experiment [11,20] and explains the absence of open isomer 8 and closed isomer 13,14 in balance (Table V). The total energies make the dominant contribution to relative stability of valence isomers, the account of zero point energy, of the thermal contribution to enthalpy and free energy make small corrections to the relative stability change.…”

Section: Valence Isomersmentioning

confidence: 97%

“…The cis-1 C 60 (NH) 2 8 is more stable in the closed form and cis-1 homodiazafullerenes C 60 (NCOOR) 2 14 and C 60 (NR*) 2 13, where R* ϭ C 4 H 2 N 3 O is nitropyrimidine group are more stable in the open form [11,20]. We have investigated a series of closed and open valence isomeris of cis-1 C 60 (NR) 2 8 -14 at the purposeful variation of R, allowing to reveal an originality of R* (Table I, Fig.…”

Section: Valence Isomersmentioning

confidence: 98%

“…In contrast to monoadducts, bis- [6,6]-open diazahomofullerenes are obtained [11,20]. The valence isomers of bis- [6,6] adducts are investigated by AM1 method [11].…”

Section: Introductionmentioning

confidence: 99%

“…The valence isomers of bis- [6,6] adducts are investigated by AM1 method [11]. In the given work, we have researched the valence isomers at the DFT/PBE/ TZ2P level using new experimental results [20]. The calculations at this level were performed earlier [20 -28].…”

Section: Introductionmentioning

confidence: 99%

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Structure and relative energies of regioisomers and valence isomers of C₆₀ adducts. HF and DFT study

Зверев

Коваленко

Romanova

et al. 2007

Int J of Quantum Chemistry

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Fullerene C 60 and N-bridged C 60 NH regioisomeres are investigated by HF and DFT methods with BLYP, B3LYP and PBE functionals at the 6-31G**, 6-311G** and TZ2P levels. Method DFT/PBE/TZ2P, providing the good compliance with experimental results, is chosen. Cross-sections of potential energy surface of adducts at a variation of 5,6-or 6,6-bonds lengths are investigated. It is shown, that C 60 C 2 H 4 NH and C 60 H 2 are characterized by local minima for [5,6]-closed forms, whereas local minima for [5,6]-open forms are absent. So absence of stable conformations of the [5,6]-closed forms of methanofullerenes and aziridinofullerenes is a consequence of strain energy in three-membered rings. It is shown that relative stability of the regioisomers depends from the lengths of single or double bonds of monoadducts, participating in reactions. The coordinated change of relative energies of the open and closed isomers N-bridged mono-(C 60 NR 1-7) and bis-adducts (C 60 (NR) 2 8 -14) is revealed. The [6,6]-closed form is more stable for compounds C 60 NR (2,3) and cis-1-C 60 (NR) 2 (9,10) (R ϭ Me, Ph), while [5,6]-open and cis-1 [6,6]-open forms are more stable for compounds C 60 NR (6,7) and cis-1-C 60 (NR) 2 (13,14) (R ϭ COOMe, R*-the nitropyrimidine), what has been confirmed by experiment. The factors, defining relative isomers stability are investigated.

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Section: Valence Isomersmentioning

confidence: 97%

Section: Valence Isomersmentioning

confidence: 97%

Section: Valence Isomersmentioning

confidence: 98%

“…In contrast to monoadducts, bis- [6,6]-open diazahomofullerenes are obtained [11,20]. The valence isomers of bis- [6,6] adducts are investigated by AM1 method [11].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structure and relative energies of regioisomers and valence isomers of C₆₀ adducts. HF and DFT study

Зверев

Коваленко

Romanova

et al. 2007

Int J of Quantum Chemistry

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Synthesis and Unusual Electrochemical Properties of Nitropyrimidine‐Substituted Diazadihomo(C₆₀‐I_h)[6,6]fullerene.

et al. 2007

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Synthesis of the individual regioisomer of the bisadduct of fullerene C60 with tert-butyl 11-azido-3,6,9-trioxaundecanoate

et al. 2007

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Synthesis and unusual electrochemical properties of nitropyrimidine-substituted diazadihomo(C60-Ih)[6,6]fullerene

Cited by 7 publications

References 16 publications

Structure and relative energies of regioisomers and valence isomers of C₆₀ adducts. HF and DFT study

Structure and relative energies of regioisomers and valence isomers of C₆₀ adducts. HF and DFT study

Synthesis and Unusual Electrochemical Properties of Nitropyrimidine‐Substituted Diazadihomo(C₆₀‐I_h)[6,6]fullerene.

Synthesis of the individual regioisomer of the bisadduct of fullerene C60 with tert-butyl 11-azido-3,6,9-trioxaundecanoate

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Synthesis and unusual electrochemical properties of nitropyrimidine-substituted diazadihomo(C60-Ih)[6,6]fullerene

Cited by 7 publications

References 16 publications

Structure and relative energies of regioisomers and valence isomers of C60 adducts. HF and DFT study

Structure and relative energies of regioisomers and valence isomers of C60 adducts. HF and DFT study