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4- and 5-nitroindane

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Abstract

Mononitration of indane produces a mixture of 4- and 5- nitroindanes. Crystallization from mixtures occurs after distillation improves composition of a major component to above 80%. 4-Nitroindane: triclinic, space group\(P\bar 1\) (#2),a=7.332(4) Å,b=8.304(4) Å,c=8.358(4) Å, α=61.43(4)°, β=67.60(4)°, γ=70.15(4)°,V=405.4(4) Å3,Z=2. Non-H-atoms are nearly planar, aliphatic H's are eclipsed. 5-Nitroindane: monoclinic, space groupP21/c (#14),a=10.946(8) Å,b=15.643(10) Å,c=9.415(6) Å, β=92.34(5)°,V=1611(2) Å3,Z=8. Non-H-atoms in the two molecules differ in torsion of the nitro group with respect to indane and fold of the nonbenzylic methylene group. Semiempirical calculations (PM3) suggest that distorsion from planarity may be associated with the two lowest energy vibrational modes. Uv, ir, ms, proton, and13C-nmr spectra are correlated with the solid state structures.

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Correspondence to Edward J. Valente.

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Fuller, J.F., Valente, E.J. 4- and 5-nitroindane. J Chem Crystallogr 26, 815–821 (1996). https://doi.org/10.1007/BF01670314

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Key Words

  • Structure
  • indane
  • indane derivatives
  • nitroindanes
  • crystallography
  • nmr
  • infrared
  • ultraviolet