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Volumn 46, Issue 8, 2007, Pages 1321-1325

Evidence for a π dimer in the electrochemical reduction of 1,3,5-trinitrobenzene: A reversible N2-fixation system

Author keywords

Azo compounds; Electrochemistry; Nitrogen fixation; Radicals; Stacking interactions

Indexed keywords

CRYSTAL STRUCTURE; ELECTROCHEMISTRY; NITROGEN FIXATION; OXIDATION;

EID: 34250819819     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602690     Document Type: Article
Times cited : (35)

References (73)
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    • Similar types of σ dimers, and occasionally π dimers, have been reported for related compounds, such as tetracyanoethylene (TCNE) derivatives: J. S. Miller, Angew. Chem. 2006, 118, 2570;
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    • Crystal structure analysis of (Et4N)2-2 (C14H23N4O6, Mr, 343.36 g mol-1, A green needle was rapidly mounted under Paratone-8277 on a glass fiber and immediately placed in a cold nitrogen stream at -80°C on a Bruker diffractometer with SMART CCD area detector. Crystal size 0.28 x 0.05 x 0.03 mm; monoclinic, space group P21/c; a, 11.657(2, b, 6.7546(14, c, 23.262(4) Å, β, 115.988(7)°, V, 1646.4(5) Å3, Z, 4; ρcalcd, 1.671 g cm-3; μ, 0.109 mm-1; 2θmax, 56.6°, λ(MoKα, 0.71073 Å. 9295 reflections collected (1535 unique reflections, R int, 0.1131, Data were corrected for absorption with the SADABS[18b] program. The structure was solved by direct methods and refined 218
    • -3. CCDC-616742 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif;
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    • 3CN was determined in relation to the fluorescence quantum yield of N′, N″,N‴-triisopropyl-4-oxo-6-isopropyliminio-2s- (2H)-triazinespiro-1′,2′,4′,6′- trinitrocyclohexadienylide (0.5);
    • 3CN was determined in relation to the fluorescence quantum yield of N′, N″,N‴-triisopropyl-4-oxo-6-isopropyliminio-2s- (2H)-triazinespiro-1′,2′,4′,6′- trinitrocyclohexadienylide (0.5);
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    • Crystal structure analysis for (Et4N)2-4 (C28H46N10O12, Mr, 714.75 g mol-1) was perfomed on a Nonius Kappa CCD diffractometer. Crystal size 0.16 x 0.07 x 0.05 mm; monoclinic, space group P2 1/c; a, 13.131(5, b, 19.359(5, c, 13.926(5) Å, β, 104.043(5)°, V, 3434(2) Å3, Z, 4; ρcalcd, 1.382 g cm-3; μ, 0.109 mm-1; 2θ, 54.7°; λ(MoKα, 0.71073 Å, T, 293(2) K. 42 967 reflections collected (7606 unique reflections, Rint, 0.1286, The structure was solved by direct methods and refined (452 parameters) by full-matrix least-squares methods on F2 with the SHELXTL package.[18c] Hydrogen atoms were calculated and placed in idealized positions. The structure was refined t
    • -3). CCDC-195183 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.
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    • [2i, 23b] Since 2 evolves spontaneously into 3, the system can be considered a dynamic switch combining chromic and magnetic outputs;
    • [2i, 23b] Since 2 evolves spontaneously into 3, the system can be considered a dynamic switch combining chromic and magnetic outputs;
  • 72


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