Pyridine, pentafluoro-
- Formula: C5F5N
- Molecular weight: 169.0522
- IUPAC Standard InChIKey: XTGOWLIKIQLYRG-UHFFFAOYSA-N
- 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
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Reaction thermochemistry data
Go To: Top, 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. 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 143. ± 8.4 | kJ/mol | TDEq | Dillow and Kebarle, 1988 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 108. ± 8.4 | kJ/mol | TDEq | Dillow and Kebarle, 1988 | gas phase |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 764.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 733.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.68 ± 0.11 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -17.2±1.0 kcal/mol , assumed entropy = 3.5 eu; B |
0.700 ± 0.050 | N/A | Van Doren, Kerr, et al., 2005 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.9 | PE | Piancastelli, Keller, et al., 1983 | LBLHLM |
9.9 | PE | Asbrink, Svensson, et al., 1981 | LLK |
10.07 | PE | Utsunomiya, Kobayashi, et al., 1978 | LLK |
10.08 | PE | Brundle, Robin, et al., 1972 | LLK |
10.27 | PE | Piancastelli, Keller, et al., 1983 | Vertical value; LBLHLM |
10.3 | PE | Asbrink, Svensson, et al., 1981 | Vertical value; LLK |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity 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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