Bicyclo[1.1.1]pentane

• Formula: C₅H₈
• Molecular weight: 68.1170
• IUPAC Standard InChI: InChI=1S/C5H8/c1-4-2-5(1)3-4/h4-5H,1-3H2 Copy

  
• IUPAC Standard InChIKey: MKCBRYIXFFGIKN-UHFFFAOYSA-N Copy
• CAS Registry Number: 311-75-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
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Gas phase thermochemistry 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Phase change 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 by: Robert L. Brown and Stephen E. Stein

Reaction thermochemistry 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 by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₅H₇^- +  =

By formula: C₅H₇^- + H⁺ = C₅H₈

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:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₅H₈⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₅H₇^- +  =

By formula: C₅H₇^- + H⁺ = C₅H₈

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.

Wiberg K.B., 1975
Wiberg K.B., Vibrational spectrum of bicyclo[1.1.1]pentane, Spectrochim. Acta, 1975, A31, 57-73. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Reed, Kass, et al., 2002
Reed, D.R.; Kass, S.R.; Mondanaro, K.R.; Dailey, W.P., Formation of a 1-bicyclo[1.1.1]pentyl anion and an experimental determination of the acidity and C-H bond dissociation energy of 3-tert-butylbicyclo[1.1.1]pentane, J. Am. Chem. Soc., 2002, 124, 11, 2790-2795, https://doi.org/10.1021/ja0121890 . [all data]

Wiberg and Connor, 1966
Wiberg, K.B.; Connor, D.S., Bicyclo[1.1.1]pentane, J. Am. Chem. Soc., 1966, 88, 4437. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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