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Synthesis and crystal structure of 1-ethyl-3-(phenyl)-1,2,3-triazolium percholorate

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The isolation of stable carbenes of the Arduengo (1a) and Wanzlick (2a) type has prompted us to look for stable nitrenium ions of the related structural type 1-ethyl-3-(phenyl)-1,2,3-triazolium perchlorate (6+). The title compound C10H14Cl N3O4 was isolated and structure was investigated by X-ray crystallography. It crystallizes in the monoclinic space group P21/c with cell parameters a=6.697(4) Å, b=9.724(9) Å, c=19.844(2) Å and Z=4. The final residual factor is R1=0.0471 for 1545 reflections with I>2σ(I). The structure exhibits intermolecular hydrogen bonds.
Physical description
1 - 12 - 2003
1 - 12 - 2003
  • [1] H. Bartsch, M. Dworkin, J.A. Miller, E.C. Miller: “Electrophilic N-acetoxyaminoarenes derived from carcinogenic N-hydroxy-N-acetylaminoarenes by enzymatic deacetylation and transacetylation in liver”, Biochem. Biophys. Acta. Vol. 286, (1972), pp. 272–298.
  • [2] Y. Berwald, L. Sachs: “In vitro cell transformation with chemical carcinogens”, Nature, Vol. 200, (1963), pp. 1182–1184.[Crossref]
  • [3] G. Boche, R.H. Sommerlade: “Oxidation of amines with bis-(diphenylphosphinyl) peroxide to give o-phosphinylated aminating reagents”, Tetrahedron, Vol. 42, (1986), pp. 2703–2706.[Crossref]
  • [4] R.A. Abramovitch, and R.A. Jeyaraman: “Reactivity and Utility”, In: (Ed.): Azides and nitrenes, Academic, Orlando, 1984, pp. 297–357.
  • [5] P.G. Gassman: “Nitrenium ions”, Acc. Chem. Res., Vol. 3, (1970), pp. 26–33.[Crossref]
  • [6] F. Bosold, G. Boche, W. Kleemissmall: “Formation of acceptor substituted phenylnitrenes via small alpha, Greek-elimination under mild conditions”, Tetrahedron Lett., Vol. 29, (1988), pp. 1780–1781.[Crossref]
  • [7] R. Uldrich, M. Famulok, F. Bosold, G. Boche: “SN2 at nitrogen: The reaction of N-(4-cyanophenyl)-O-diphenylphosphinoylhydroxylamine with N.Methylaniline. A model for the reactions of ultimate carcinogens of aromatic amines with (bio) nucleophiles”, Tetrahedron Lett., Vol. 31, (1990), pp. 1689–1692.[Crossref]
  • [8] G.B. Anderson and D.E. Falvey: “Photogenerated arylnitrenium ions: absorption spectra and absolute rate constants for tert-butyl(4-halo-2-acetylphenyl)nitrenium ions measured by time-resolved laser spectroscopy”, J. Am. Chem. Soc., Vol. 115, (1993), pp. 9870–9871.[Crossref]
  • [9] A.J. Arduengo, R.L. Harlow, M. Kline: “A stable crystalline carbene”, J. Am. Chem. Soc., Vol. 113, (1991), pp. 361–363.[Crossref]
  • [10] H.W. Wanzlick: “Aspects of nucleophilic carbene chemistry”, Angew. Chem. Int. Ed. Engl., Vol. 1, (1962), pp. 75–80.[Crossref]
  • [11] G. Boche, P. Andrews, K. Harms, M. Marsch, K.S. Rangappa, M. Schimeczek, C. Willeke: “Crystal and Electronic Structure of Stable Nitrenium ions. A Comparison with Structurally Related Carbenes”, J Am. Chem. Soc., Vol. 118, (1996), pp. 4925–4930.[Crossref]
  • [12] G. Boche, K.S. Rangappa, K. Harms, M. Marsch: “Crystal structure of 1-benzyl-3-methyl-1,2,3-triazolinium perchlorate, (C6H5)(N3C3H7)+(ClO4)−”, Z. Kristallogr., Vol. 211, (1996), pp. 581–582.[Crossref]
  • [13] M.A. Sridhar, N.K. Lokanath, J. Shashidhara Prasad, D.G. Bhadregowda, K.S. Rangappa: “Crystal structure of 1-methyl-3-phenyl-1,2,3-triazolinium perchlorate, C9H12N3(ClO4)”, Z. Kristallogr., Vol. 212, (1997), pp. 33–34.[Crossref]
  • [14] R. Marc, N. Andreas, G. Boche, K.S. Rangappa, P. Andrews: “Electron transfer chemistry of some unusal nitrogen compounds: from stable nitrenium ions to the corresponding nitrogen centered radicals”, New. J. Chem., Vol. XyX, (1998), pp. 1437–1444.
  • [15] K.S. Rangappa, H. Mallesha, N.V. AnilKumar, N.K. Lokanath, M.A. Sridhar, J. Shashidhara Prasad: “Synthesis and crystal structure of 1,3-dimethyl benzotriazolium trifluoromethane sulfonate”, Mol. Cryst. Liq. Cryst., Vol. 357, (2001), pp. 291–298.
  • [16] R.J. Moran, C. Cramer, D.E. Falvey: ”Reactions of Diarylnitrenium Ions with Electron Rich Alkenes: An Experimental and Theoretical Study”, J. Org. Chem., Vol. 62, (1997), pp. 2742–2751.[Crossref]
  • [17] S. Mackay, C.J. Gilmore, C. Edwards, N. Stewart, K. Shankland: “maXus Computer Program for the Solution and Refinement of Crystal Structures”, Bruker Nonius, The Netherlands, MacScience, Japan and The University of Glasgow, 1999.
  • [18] C.K. Johnson: “ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138”, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA, 1976.
  • [19] Z. Otwinowski, W. Minor: “In Methods in Enzymology”, Vol. 276, edited by C.W. Carter, Jr., R.M. Sweet, Academic Press, New York, 1997, pp. 307–326.
  • [20] G.M. Sheldrick: “SHELXS-97. Program for Crystal Structure Solution”, University of Göttingen, Germany, 1997.
  • [21] G.M. Sheldrick: “SHELXL-97. Program for the Refinement of Crystal Structures” University of Göttingen, Germany, 1997.
  • [22] Z. Berkovitch-Yellin, L. Leiserowitz: “The role played by C−H…O and C−H…N interactions in determining molecular packing and conformation”, Acta Cryst., Vol. B40, (1984), pp. 159–165.[Crossref]
  • [23] G.A. Jeffrey, H. Maluszynska, J. Mitra: “Hydrogen bonding in nucleosides and nucleotides”, Int. J. Biol. Macromol, Vol. 7, (1985), pp. 3336–348.[Crossref]
  • [24] Bondi A.: “van der Waals Volumes and Radii”, J. Phys. Chem., Vol. 64, (1964), pp. 441–451.
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