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Journal of Chemical Crystallography

, Volume 44, Issue 2, pp 98–102 | Cite as

Structural Analysis of Methyl-Substituted Nitrosobenzenes and Nitrosoanisoles

  • Eric BoschEmail author
Original Paper

Abstract

The structures of a series of simple nitrosoarenes: o-nitrosotoluene, nitrosomesitylene, nitrosoprehnitene, 2-methyl-4-nitrosoanisole and 2,6-dimethyl-4-nitrosoanisole are reported. The nitrosoarenes studied adopt one of two orientations in the solid state. In one group (nitrosophrenitene, 2,6-dimethyl-4-nitrosoanisole and 2-methyl-4-nitrosoanisole) the nitroso moiety is coplanar with the arene and the nitrosoarenes exist as monomers (ArNO) in the solid state. In contrast the nitroso group in o-nitrosotoluene and nitrosomesitylene is orthogonal to the arene and these nitrosoarenes exist as trans dimers ArN(O)N(O)Ar.

Graphical Abstract

The structures of a series of simple nitrosoarenes: o-nitrosotoluene, nitrosomesitylene, nitrosoprehnitene, 2-methyl-4-nitrosoanisole and 2,6-dimethyl-4-nitrosoanisole are reported.

Keywords

Nitrosobenzene Nitrosoanisole 

Notes

Acknowledgments

The Missouri State University Provost Incentive Fund funded the purchase of the X-Ray diffractometer.

References

  1. 1.
    Fletcher DA, Gowenlock BG, Orrell KG (1998) J Chem Soc Perkin Trans 2:797–803CrossRefGoogle Scholar
  2. 2.
    Orrell KG, Sik V, Stephenson D (1987) Magn Reson Chem 25:1007CrossRefGoogle Scholar
  3. 3.
    Talberg HJ (1979) Acta Chem Scand A 33:289–296CrossRefGoogle Scholar
  4. 4.
    Janbon S, Davey RJ, Shankland K (2008) CrystEngComm 10:279–282CrossRefGoogle Scholar
  5. 5.
    Halasz J, Mestrovic E, Cicak H, Mihalic Z, Vancik H (2005) J Org Chem 70:8461CrossRefGoogle Scholar
  6. 6.
    Darnin C, Hodgkin DC (1950) Nature 166:827–828Google Scholar
  7. 7.
    Webster MS (1956) J Chem Soc 2841Google Scholar
  8. 8.
    Fletcher DA, Gowenlock BG, Orrell KG, Sik Hibbs DE, Hursthouse MB, Malik KMA (1996) J Chem Soc Perkin Trans 2:191CrossRefGoogle Scholar
  9. 9.
    Dieterich DA, Paul IC, Curtin DY (1974) J Am Chem Soc 96:6372CrossRefGoogle Scholar
  10. 10.
    Dickie DA, MacIntosh IS, Ino DD, He Q, Labeodan OA, Jennings MA, Schatte G, Walsby CJ, Clyburne JAC (2008) J Am Chem Soc 86:20Google Scholar
  11. 11.
    Bosch E, Kochi JK (1994) J Org Chem 59:5573–5586CrossRefGoogle Scholar
  12. 12.
    (2006) ApexII Suite. Bruker AXS Ltd., MadisonGoogle Scholar
  13. 13.
    Sheldrick GM (2008) Acta Crystallogr Sect A 64:112CrossRefGoogle Scholar
  14. 14.
    Barbour L, Atwood JA (2003) Cryst Growth Design 3:3CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Chemistry DepartmentMissouri State UniversitySpringfieldUSA

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