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Structural Analysis of Methyl-Substituted Nitrosobenzenes and Nitrosoanisoles

Journal of Chemical Crystallography volume 44, pages 98–102 (2014)Cite this article

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.

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Acknowledgments

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

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  1. Chemistry Department, Missouri State University, 901 South National Avenue, Springfield, MO, 65897, USA

    Eric Bosch

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  1. Eric Bosch
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Correspondence to Eric Bosch.

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Bosch, E. Structural Analysis of Methyl-Substituted Nitrosobenzenes and Nitrosoanisoles. J Chem Crystallogr 44, 98–102 (2014). https://doi.org/10.1007/s10870-013-0489-8

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  • DOI: https://doi.org/10.1007/s10870-013-0489-8

Keywords

  • Nitrosobenzene
  • Nitrosoanisole