Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

[2.2]Paracyclophane

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas244.7 ± 2.1kJ/molCcbNishiyama, Sakiyama, et al., 1980Reanalyzed by Cox and Pilcher, 1970, Original value = 246.3 ± 3.3 kJ/mol
Deltafgas241. ± 4.2kJ/molCcbRodgers, Westrum, et al., 1973 
Deltafgas241.3 ± 4.3kJ/molCcbBoyd, 1966Reanalyzed by Cox and Pilcher, 1970, Original value = 251. ± 7.9 kJ/mol

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafsolid146.7 ± 2.8kJ/molCcbNishiyama, Sakiyama, et al., 1980ALS
Deltafsolid144.7 ± 0.88kJ/molCcbRodgers, Westrum, et al., 1973ALS
Deltafsolid154. ± 4.kJ/molCcbBoyd, 1966ALS
Quantity Value Units Method Reference Comment
Deltacsolid-8729.5 ± 1.8kJ/molCcbNishiyama, Sakiyama, et al., 1980Corresponding «DELTA»fsolid = 146.68 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-8727.57 ± 0.63kJ/molCcbRodgers, Westrum, et al., 1973Corresponding «DELTA»fsolid = 144.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-8737. ± 4.kJ/molCcbBoyd, 1966Corresponding «DELTA»fsolid = 154. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar265.68J/mol*KN/AAndrews and Westrum, 1970DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
252.7298.15Rodgers, Westrum, et al., 1973Cp given as 0.290 cal/g*K.; DH
252.34298.15Andrews and Westrum, 1970T = 10 to 350 K.; DH
248.1300.Shieh, McNally, et al., 1969T = 300, 318 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Deltasub98.0kJ/molN/ANishiyama, Sakiyama, et al., 1980DRB
Deltasub96.2 ± 4.2kJ/molVRodgers, Westrum, et al., 1973ALS
Deltasub96.3kJ/molN/ARodgers, Westrum, et al., 1973DRB
Deltasub96.2 ± 4.2kJ/molVBoyd, 1966ALS
Deltasub87.3kJ/molN/ABoyd, 1966DRB

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
99.6 ± 1.8381.4VNishiyama, Sakiyama, et al., 1980ALS
96.4 ± 1.5353. - 409.TSGCNishiyama, Sakiyama, et al., 1980AC
92.9 ± 0.84363.MEBoyd, 1966Based on data from 343. - 383. K. See also Stephenson and Malanowski, 1987 and Cox and Pilcher, 1970, 2.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
0.21323.2Andrews and Westrum, 1970, 2AC

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

IR spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118477

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Nishiyama, Sakiyama, et al., 1980
Nishiyama, K.; Sakiyama, N.; Seki, S.; Horita, H.; Otsubo, T.; Misumi, S., Thermochemical studies on double- and triple-layered [2.2]paracyclophanes. Estimation of molecular strain energies., Bull. Chem. Soc. Jpn., 1980, 53, 869-877. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Rodgers, Westrum, et al., 1973
Rodgers, D.L.; Westrum, E.F., Jr.; Andrews, J.T.S., The enthalpies of combustion and formation of [2.2]-paracyclophane and triptycene, J. Chem. Thermodyn., 1973, 5, 733-739. [all data]

Boyd, 1966
Boyd, R.H., The heat of combustion and strain energy of 2,2-paracyclophane, Tetrahedron, 1966, 22, 119-122. [all data]

Andrews and Westrum, 1970
Andrews, J.T.S.; Westrum, E.F., Jr., The heat capacity and thermodynamic functions of crystalline and liquid triptycene, J. Chem. Thermodynam., 1970, 2, 245-253. [all data]

Shieh, McNally, et al., 1969
Shieh, C.; McNally, D.; Boyd, R.H., The heats of combustion and strain energies of some cyclophanes, Tetrahedron, 1969, 3653-3665. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Andrews and Westrum, 1970, 2
Andrews, John T.S.; Westrum, Edgar F., Heat capacity and thermodynamic properties of [2.2]paracyclophane. Mechanism of the 50.deg.K transition, J. Phys. Chem., 1970, 74, 10, 2170-2174, https://doi.org/10.1021/j100909a022 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References