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Volumn 47, Issue 14, 2008, Pages 6118-6120

Synthesis and characterization of the 4,4′-bipyridyl dianion and radical monoanion. A structural study

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EID: 48749116364 PISSN: 00201669 EISSN: None Source Type: Journal
DOI: 10.1021/ic800726p Document Type: Article

Times cited : (49)

References (16)

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10
- 48749108153
- All operations were carried out under an inert atmosphere using standard Schlenk-line or glovebox techniques. In a typical experiment, 4,4′-bipyridine (0.150 g, 0.96 mmol) and sodium metal (0.024 g, 1.04 mmol) were weighed out into a test tube inside a nitrogen-filled glovebox (H 2O < 0.1 ppm; O2 < 0.1 ppm, The solids were dissolved in approximately 5 mL of dry en, which immediately yielded a dark-purple solution. The mixture was allowed to stir overnight and subsequently filtered into a clean ampule. The purple solution was concentrated in vacuo on a Schlenk-line until half of the solvent had been removed. This solution was layered with benzene, yielding dark-purple blocklike crystals suitable for single-crystal X-ray diffraction after approximately 24 h 73% crystalline yield, Anal. Calcd for C12H16N4Na: C, 60.24; H, 6.74; N, 23.41. Found: C, 60.12; H, 6.71; N, 23.36
- 4Na: C, 60.24; H, 6.74; N, 23.41. Found: C, 60.12; H, 6.71; N, 23.36.

11
- 48749118183
- All single-crystal X-ray diffraction data were collected on an Enraf-Nonius Kappa-CCD diffractometer equipped with an Oxford Cryosystems low-temperature device. Crystals were mounted on a glass fiber using N-Paratone oil and quickly placed under the nitrogen flow of the cryostream. Data were collected using graphite-monochromated Mo Kα radiation; equivalent reflections were merged, and the images were processed with the DENZO and SCALEPACK programs. Corrections for Lorentz-polarization effects and absorption were performed, and the structures were solved by direct methods using SHELXS. The structures were refined on F2 using SHELXL. Crystal data for Na(bipy)ien, 1, monoclinic, C2/c; a, 13.4043(4) Å, b, 9.7710(4) Å, c, 10.3943(4) Å, β, 109.618(2)°; V, 1282.4(8) Å3; Z, 4; T, 150(2) K; R1, 0.043, wR2, 0.108 [I > 2σ
- 3; Z = 8; T = 250(2) K; R1 = 0.069, wR2 = 0.195 [I > 2σ(I)]; R1 = 0.087, wR2 = 0.207 (all data).

12
- 48749119231
- 3Na: C, 52.16; H, 7.50; N, 26.07. Found: C, 52.07; H, 7.53; N, 26.03.
- 3Na: C, 52.16; H, 7.50; N, 26.07. Found: C, 52.07; H, 7.53; N, 26.03.

13
- 0000647428
- and references cited therein. For an overview of 4,4′-bipyridine in modular networks, see
- For an overview of 4,4′-bipyridine in modular networks, see: Yaghi, O. M.; Li, H.; Davis, C.; Richardson, D.; Groy, T. L. Acc. Chem. Res. 1998, 31, 474, and references cited therein.
- (1998) Acc. Chem. Res , vol.31 , pp. 474
- Yaghi, O.M.¹ Li, H.² Davis, C.³ Richardson, D.⁴ Groy, T.L.⁵

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15
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- DFT calculations performed using B3LYP/3-21+G* and the Gaussian03 package: Frisch, M. J. Gaussian03, revision D.01; Gaussian Inc.: Wallingford, CT, 2004.
- DFT calculations performed using B3LYP/3-21+G* and the Gaussian03 package: Frisch, M. J. Gaussian03, revision D.01; Gaussian Inc.: Wallingford, CT, 2004.

16
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