[2.2]Paracyclophane
- Formula: C16H16
- Molecular weight: 208.2982
- IUPAC Standard InChIKey: OOLUVSIJOMLOCB-UHFFFAOYSA-N
- CAS Registry Number: 1633-22-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene; Cyclobis(benzene-1,4-dimethylene); Di-p-xylylene; Di-1,4-xylylene; tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 244.7 ± 2.1 | kJ/mol | Ccb | Nishiyama, Sakiyama, et al., 1980 | Reanalyzed by Cox and Pilcher, 1970, Original value = 246.3 ± 3.3 kJ/mol |
ΔfH°gas | 241. ± 4.2 | kJ/mol | Ccb | Rodgers, Westrum, et al., 1973 | |
ΔfH°gas | 241.3 ± 4.3 | kJ/mol | Ccb | Boyd, 1966 | Reanalyzed by Cox and Pilcher, 1970, Original value = 251. ± 7.9 kJ/mol |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C16H16+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.8 | PE | Gleiter, Eckert-Maksic, et al., 1982 | LBLHLM |
7.8 | PE | Kovac, Mohraz, et al., 1980 | LLK |
7.60 | PE | Heilbronner and Maier, 1974 | LLK |
~7.8 | PI | Pignataro, Mancini, et al., 1971 | LLK |
8.2 | PE | Gleiter, Eckert-Maksic, et al., 1982 | Vertical value; LBLHLM |
8.10 | PE | Zhong-zhi, Kovak, et al., 1981 | Vertical value; LLK |
8.10 | PE | Kovac, Allan, et al., 1980 | Vertical value; LLK |
8.00 | PE | Koenig, Wielesek, et al., 1975 | Vertical value; LLK |
8.08 | PE | Boschi and Schmidt, 1973 | Vertical value; LLK |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, 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
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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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 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
Gleiter, Eckert-Maksic, et al., 1982
Gleiter, R.; Eckert-Maksic, M.; Schafer, W.; Truesdale, E.A.,
Quest for a strong through bond interaction in [2.2]paracyclophane,
Chem. Ber., 1982, 115, 2009. [all data]
Kovac, Mohraz, et al., 1980
Kovac, B.; Mohraz, M.; Heilbronner, E.; Boekelheide, V.; Hopf, H.,
Photoelectron spectra of the cyclophanes,
J. Am. Chem. Soc., 1980, 102, 4314. [all data]
Heilbronner and Maier, 1974
Heilbronner, E.; Maier, J.P.,
Consequences of substitution in the photoelectron spectra of [2,2] paracyclophanes: separation of 'through-space' and 'through-bond' interactions as a consequence of fluorosubstitution,
Helv. Chim. Acta, 1974, 57, 151. [all data]
Pignataro, Mancini, et al., 1971
Pignataro, S.; Mancini, V.; Ridyard, J.N.A.; Lempka, H.J.,
Photoelectron energy spectra of molecules having classically non-conjugated π-systems,
Chem. Commun., 1971, 142. [all data]
Zhong-zhi, Kovak, et al., 1981
Zhong-zhi, Y.; Kovak, B.; Heilbronner, E.; Eltamany, S.; Hopf, H.,
192. Ionization energies of methyl-substituted [2.2] paracyclophanes,
Helv. Chim. Acta, 1981, 64, 1991. [all data]
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, Wielesek, et al., 1975
Koenig, T.; Wielesek, R.; Snell, W.; Balle, T.,
Helium(I) photoelectron spectrum of p-quinodimethane,
J. Am. Chem. Soc., 1975, 97, 3225. [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
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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