[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 ion energetics data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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
7.8PEGleiter, Eckert-Maksic, et al., 1982LBLHLM
7.8PEKovac, Mohraz, et al., 1980LLK
7.60PEHeilbronner and Maier, 1974LLK
~7.8PIPignataro, Mancini, et al., 1971LLK
8.2PEGleiter, Eckert-Maksic, et al., 1982Vertical value; LBLHLM
8.10PEZhong-zhi, Kovak, et al., 1981Vertical value; LLK
8.10PEKovac, Allan, et al., 1980Vertical value; LLK
8.00PEKoenig, Wielesek, et al., 1975Vertical value; LLK
8.08PEBoschi and Schmidt, 1973Vertical value; LLK

IR Spectrum

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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

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 ion energetics data, IR Spectrum, UV/Visible 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).

Due to licensing restrictions, this spectrum cannot be downloaded.

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.


UV/Visible spectrum

Go To: Top, Gas phase ion energetics 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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

UVVis 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.

Source Cram, Dalton, et al., 1963
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 386
Instrument Cary PMS 11

References

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

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]

Cram, Dalton, et al., 1963
Cram, D.J.; Dalton, C.K.; Knox, G.R., Macro rings. XXIX. Stereochemistry of a 1,6-cycloaddition reaction, J. Am. Chem. Soc., 1963, 85, 1088-1093. [all data]


Notes

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References