(2.2)Metacyclophane

• Formula: C₁₆H₁₆
• Molecular weight: 208.2982
• IUPAC Standard InChI: InChI=1S/C16H16/c1-3-13-7-9-15-5-2-6-16(12-15)10-8-14(4-1)11-13/h1-6,11-12H,7-10H2 Copy

  
• IUPAC Standard InChIKey: COTONUHLIMVDNV-UHFFFAOYSA-N Copy
• CAS Registry Number: 2319-97-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Tricyclo[9.3.1.1^4,8]hexadeca-1(15),4,6,8(16),11,13-hexaene; Di-m-xylylene; Di-1,3-xylylene; Tricyclo(9.3.1.14,8)hexadeca-1(15),4,6,8(16),11,13-hexaene; Triple-layered-(2.2)metacyclophane
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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
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Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₁₆H₁₆⁺ (ion structure unspecified)

Ionization energy determinations

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Kovac, Allan, et al., 1980
Kovac, B.; Allan, M.; Heilbronner, E.; Maier, J.P.; Gleiter, R.; Haenel, M.W.; Keehn, P.M.; Reiss, J.A., He(Iα) photoelectron spectra of [2.2]cyclophanes, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 167. [all data]

Koenig, Tuttle, et al., 1974
Koenig, T.; Tuttle, M.; Wielesek, R.A., The He(I) photoelectron spectra of xylenes and metacyclophanes. A reassignment of the lowest ionic state of [2.2] metacyclophane, Tetrahedron Lett., 1974, 2537. [all data]

Boschi and Schmidt, 1973
Boschi, R.; Schmidt, W., Transannular π - π interaction in cyclophanes, Angew. Chem. Int. Ed. Engl., 1973, 12, 402. [all data]

Notes

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• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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