1004-16-6Relevant articles and documents
The influence of weak hydrogen bonds on the properties of 3-cyano-N-methylpyridinium chloride and iodide
Koplitz, Lynn Vogel,Bay, Kevin D.,DiGiovanni, Neil,Mague, Joel T.
, p. 391 - 402 (2003)
The iodide salt of 3-cyano-N-methylpyridinium cation crystallizes as yellow needles in the monoclinic space group P21/n with a = 4.8726(5), b = 12.9380(15), c = 13.4629(15) A, β = 97.463(2)°, and Z = 4 (mp 196°C). The chloride salt forms colorless plates in the monoclinic space group P21/m with a = 7.9488(8), b = 6.4023(7), c = 8.0844(8) A, β = 112.987(2)°, and Z = 2 (mp > 220°C). For ring hydrogens interacting with the anion, each salt has C-H ... X distances and angles consistent with weak hydrogen bonds as described by recently published criteria (Brammer et al. Cryst. Growth Design 2001, 1, 277; Steiner Acta Crystallogr., Sect B 1998, 54, 456; Crystallogr. Rev. 1996, 6, 1). The chloride salt has an additional interaction between H5 and the cyano nitrogen on an adjacent cation in the same layer, or a total of four coplanar hydrogen bonds per cation. It forms sheets which stack along the b axis. The iodide has fewer hydrogen bonds from the ring and the cations are tilted relative to each other. There is an unusual hydrogen bond from a methyl hydrogen to a cyano nitrogen in the iodide. Roughly oval (3.8 x 5.7 A) open channels bounded by H5 and iodides run along the a axis. Stabilization of these solids by hydrogen bonding is estimated to be at least 1.9 kcal/mole more for the chloride than for the iodide.
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Mukherjee,Chatterjee
, p. 1461,1466 (1966)
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Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts
Kiamehr, Mostafa,Moghaddam, Firouz Matloubi,Mkrtchyan, Satenik,Semeniuchenko, Volodymyr,Supe, Linda,Villinger, Alexander,Langer, Peter,Laroshenko, Viktor O.
supporting information, p. 1119 - 1126 (2013/07/19)
The cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[7.3.1.0 2,7]trideca-2(7),11-dienes. The reaction proceeds by regioselective attack of the central carbon atom of t
Quantitative in situ measurement of ion transport in polypyrrole/poly(styrenesulfonate) films using rotating ring-disk voltammetry
Salzer, Corey A.,Elliott, C. Michael,Hendrickson, Susan M.
, p. 3677 - 3683 (2007/10/03)
An approach based on rotating ring-disk electrode (RRDE) voltammetry is described for the quantitative, in situ measurement of ion transport between solution and conducting polymer films. The specific composite film studied in this report is polypyrrole/poly(styrenesulfonate) (pPy+/pSS-). Cation flux in and out of the polymer was obtained from the mass-transport-limited reduction current for the dopant cation(s) measured at the ring during redox cycling of the polymer. Crucial to this method is the use of a supporting electrolyte that is sterically inhibited from passing into the film and the use of dopant ions that adhere to specific electrochemical constraints. With this method it was possible to quantitatively account for all changes in charge compensation in the film by the specific cation(s) involved. Three different cations were explored alone and in paired combinations. Solutions containing mixtures of dopant cations were studied to determine whether the pPy+/pSS- films exhibit preferential doping. Kinetic factors, likely due to steric differences in the dopant cations, were found to lead to significant preferential doping of the polymer.