4,4'-Bipyridine
- Formula: C10H8N2
- Molecular weight: 156.1839
- IUPAC Standard InChI: InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H
- IUPAC Standard InChIKey: MWVTWFVJZLCBMC-UHFFFAOYSA-N
- CAS Registry Number: 553-26-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: γ,γ'-Bipyridyl; γ,γ'-Dipyridyl; 4,4-Bipyridyl; 4,4-Dipyridyl; 4,4'-Bipyridyl; 4,4'-Dipyridine; 4,4'-Dipyridyl; 4,4-Bipyridine; 4-(4-Pyridyl)pyridine; Bipyridine, 4,4'-; NSC 404423
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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 | 70.05 ± 0.86 | kcal/mol | Ccb | Ribeiro da Silva, Morais, et al., 1995 |
Condensed phase thermochemistry data
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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°solid | 44.65 ± 0.53 | kcal/mol | Ccb | Ribeiro da Silva, Morais, et al., 1995 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1258.4 ± 0.43 | kcal/mol | Ccb | Ribeiro da Silva, Morais, et al., 1995 |
Phase change data
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 578.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 578. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 17.0 ± 0.62 | kcal/mol | CGC | Lipkind and Chickos, 2009 | See also Lipkind, Hanshaw, et al., 2009.; AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 25.41 ± 0.67 | kcal/mol | C | Ribeiro da Silva, Morais, et al., 1995 | ALS |
| ΔsubH° | 25.41 | kcal/mol | N/A | Ribeiro da Silva, Morais, et al., 1995 | DRB |
| ΔsubH° | 25.41 ± 0.67 | kcal/mol | C | Ribeiro da Silva, Morais, et al., 1995 | AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 3.85 | 377.5 | DSC | Lipkind, Hanshaw, et al., 2009 | AC |
Gas Chromatography
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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
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1507. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CAM | 2453. | Premecz and Ford, 1987 | He, 60. C @ 5. min, 5. K/min, 240. C @ 21. min; Column length: 15. m; Column diameter: 0.24 mm |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Other | Methyl Silicone | 1507. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro da Silva, Morais, et al., 1995
Ribeiro da Silva, M.A.V.; Morais, V.M.F.; Matos, M.A.R.; Rio, C.M.A.,
Thermochemical and theoretical studies of some bipyridines,
J. Org. Chem., 1995, 60, 5291-5294. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Lipkind and Chickos, 2009
Lipkind, D.; Chickos, J.S.,
, Abstract from 38th Great Lakes Regional Meeting of the American Chemical Society, May 13-16, Chicago, IL, 2009, GLRM-275. [all data]
Lipkind, Hanshaw, et al., 2009
Lipkind, Dmitri; Hanshaw, William; Chickos, James S.,
Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Heterocycles and Related Compounds,
J. Chem. Eng. Data, 2009, 54, 10, 2930-2943, https://doi.org/10.1021/je900034d
. [all data]
Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses,
J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1
. [all data]
Premecz and Ford, 1987
Premecz, J.E.; Ford, M.E.,
Gas chromatographic separation of substituted pyridines,
J. Chromatogr., 1987, 388, 23-35, https://doi.org/10.1016/S0021-9673(01)94463-2
. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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