Pyridine, pentafluoro-

• Formula: C₅F₅N
• Molecular weight: 169.0522
• IUPAC Standard InChI: InChI=1S/C5F5N/c6-1-2(7)4(9)11-5(10)3(1)8 Copy

  
• IUPAC Standard InChIKey: XTGOWLIKIQLYRG-UHFFFAOYSA-N Copy
• CAS Registry Number: 700-16-3
• 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: Pentafluoropyridine; Perfluoropyridine; 2,3,4,5,6-Pentafluoropyridine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Phase change data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Reaction thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering 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: 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

 +  = ( • )

By formula: F^- + C₅F₅N = (F^- • C₅F₅N)

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

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
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

Ion clustering data

Go To: Top, Phase change data, Reaction 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: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: F^- + C₅F₅N = (F^- • C₅F₅N)

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

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

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [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]

Banks, Ginsberg, et al., 1961
Banks, R.E.; Ginsberg, A.E.; Haszeldine, R.N., 338. Heterocyclic polyfluoro-compounds. Part I. Pentafluoropyridine, J. Chem. Soc., 1961, 1740, https://doi.org/10.1039/jr9610001740 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Dillow and Kebarle, 1988
Dillow, G.W.; Kebarle, P., Fluoride Affinities of Perfluorobenzenes C₆F₅X. Meisenheimer Complexes in the Gas Phase and Solution, J. Am. Chem. Soc., 1988, 110, 15, 4877, https://doi.org/10.1021/ja00223a001 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P., Substituent Effects on the Electron Affinities of Perfluorobenzenes C₆F₅X, J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014 . [all data]

Van Doren, Kerr, et al., 2005
Van Doren, J.M.; Kerr, D.M.; Miller, T.M.; Viggiano, A.A., Electron attachment and detachment, and the electron affinities of C5F5N and C5HF4N, J. Chem. Phys., 2005, 123, 11, 114303, https://doi.org/10.1063/1.2032967 . [all data]

Piancastelli, Keller, et al., 1983
Piancastelli, M.N.; Keller, P.R.; Taylor, J.W.; Grimm, F.A.; Carlson, T.A., Angular distribution parameter as a function of photon energy for some mono- and diazabenzenes and its use for orbital assignment, J. Am. Chem. Soc., 1983, 105, 4235. [all data]

Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G., 30.4 nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [all data]

Utsunomiya, Kobayashi, et al., 1978
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some pyridines, Bull. Chem. Soc. Jpn., 1978, 451, 3482. [all data]

Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A., Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules, J. Am. Chem. Soc., 1972, 94, 1466. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  EA	Electron affinity
  Tboil	Boiling point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.