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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References
Lindner, J.; Bruhin, J.Berichte 1927,60B, 435.
Galceran, M.T.; Moyano, J.,J. Chromatog. 1992,607, 287.
Liu, T.-Y.; Robbat, A.;J. Chromatog. 1991;539, 1.
McKinney, T.M.; Geske, D.H..J. Amer. Chem. Soc. 1967,89, 2806.
Pailer, M.; Grünhaus, H.Monatscheft für Chemie 1974,105, 1362.
Tuominen, J. Wickstrom, K.; Pyysalo, H.J. High. Resol. Chromatog. Chromatog. Commun. 1986,10633, 469.
HYPERCHEM for Windows, Hypercube, Inc. Waterloo, Ontario, Canada, © 1994.
Allinger, N.L.J. Amer. Chem. Soc. 1977,99, 8127; and Allinger, N.L. “QCPE395-MM2,” Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN.
Stewart, J.J.P.;J. Comput. Chem. 1991,12, 320, and Stewart, J.J.P., “QCPE #506,” Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN.
Varsanyi, G., Molnar-Paal, E., Kosa, K.; Keresztury, G.;Acta Chim. Acad. Sci. Hung. 1979,100, 481; and Suranarayana, V., Kumar, A.P., Rao, G.R.: Pandey, G.C.Spectrochim Acta.1992,48a, 1481.
Korseniewski, C.; Kowalchyk, C.;J. Phys. Chem. 1991,95, 68.
Schatz, P.; Reich, H.J. RACCOON. Program for simulation and analysis of multispin proton magnetic Resonance spectra, University of Wisconsin. Madison, WI1993.
Levy, G.C.; Nelson, G.L.Carbon-13 Nuclear Magnetic Resonance for Organic Chemists; Wiley-Interscience. New York,1972.
Burgi, H.-B.; Dunitz, J.D.Structure Correlation, Volume 2; VCH Publishers: New York,1994, Appendix A.
De Ridder D.J.A.; Schenk, H.Acta Crystallogr. 1994,B50, 724.
Sheldrick, G. Programs for solution and refinement of crystal and molecular structures from X-ray diffraction data. SHELXS-86.Acta Crystallogr 1990,A46, 467.
Sheldrick G. (SHELXL-93):Crystallographic Computing; Oxford University Press; Oxford, UK,1992.
International Tables for X-Ray Crystallography; D. Reidel Publishing, Volume IV; 1985.
De Ridder, D.J.A.; Schenk, H..Acta Crystallogr. 1995,B51 231.
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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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DOI: https://doi.org/10.1007/BF01670314