2,2'-Bipyridine
- Formula: C10H8N2
- Molecular weight: 156.1839
- IUPAC Standard InChIKey: ROFVEXUMMXZLPA-UHFFFAOYSA-N
- CAS Registry Number: 366-18-7
- 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: α,α'-Bipyridine; α,α'-Bipyridyl; α,α'-Dipyridine; α,α'-Dipyridyl; 2,2'-Bipyridyl; 2,2'-Dipyridine; 2,2'-Dipyridyl; AA-DP; Bipyridine; CI 588; 2,2'-Bipyridin; 2-(2-Pyridyl)pyridine; NSC 1550; NSC 615009
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Gas phase ion energetics data
Go To: Top, 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 as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
223.1 ± 1.5 | Oresmaa, Haukka, et al., 2002 | 2,3-Dimethylpyridine; N,N-Dimethylisopropylamine. Paper reports PAs, however PT reactivity brackets GBs. Uncertainty is half the GB difference between bracketing bases.; MM |
>217. | Shen and Brodbelt, 1998 | GB > 18-Crown-6. From PT bracketing at nominal 300 K, but ion energies are undefined. Reference GB readjusted to Hunter and Lias, 1998; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.6 | PE | Dobson, Hillier, et al., 1983 | LBLHLM |
8.35 ± 0.02 | PE | Maier and Turner, 1972 | LLK |
8.85 | PE | Dobson, Hillier, et al., 1983 | Vertical value; LBLHLM |
Gas Chromatography
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1472. | Premecz and Ford, 1987 | He, 60. C @ 10. min, 10. K/min, 280. C @ 3. min; Column length: 30. m; Column diameter: 0.32 mm |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CAM | 2193. | 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, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 1444. | Chen and Ho, 1998 | 60. m/0.32 mm/1.0 μm, He, 3. K/min; Tstart: 40. C; Tend: 260. C |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 245.68 | Blanco, Blanco, et al., 1989 | H2, 4. K/min; Column length: 25. m; Column diameter: 0.22 mm; Tstart: 50. C; Tend: 300. C |
Capillary | SE-52 | 247.15 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Capillary | SE-52 | 245.48 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Oresmaa, Haukka, et al., 2002
Oresmaa, L.; Haukka, M.; Vainiotalo, P.; Pakkanen, T.A.,
Ab intio calculations and mass spectrometric determination of the gas phase proton affinities of 4,4'-disubstituted 2,2'-bipyridines,
J. Org. Chem., 2002, 67, 8216. [all data]
Shen and Brodbelt, 1998
Shen, J.; Brodbelt, J.,
Evaluation of proton-binding capabilities of polyether and pyridyl ligands,
J. Mass Spectrom., 1998, 33, 118. [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]
Dobson, Hillier, et al., 1983
Dobson, B.; Hillier, I.H.; Connor, J.A.; Moncrieff, D.; Scanlan, M.L.; Garner, C.D.,
Electronic structure and low-energy photoelectron spectra of 4,4'-disubstituted 2,2'-bipyridines,
J. Chem. Soc. Faraday Trans. 2, 1983, 79, 295. [all data]
Maier and Turner, 1972
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls,
Faraday Discuss. Chem. Soc., 1972, 54, 149. [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]
Chen and Ho, 1998
Chen, J.; Ho, C.-T.,
Volatile compounds formed from thermal degradation of glucosamine in a dry system,
J. Agric. Food Chem., 1998, 46, 5, 1971-1974, https://doi.org/10.1021/jf971021o
. [all data]
Blanco, Blanco, et al., 1989
Blanco, C.G.; Blanco, J.; Bermejo, J.; Guillen, M.D.,
Capillary gas chromatography of some polycyclic aromatic compounds on several stationary phases,
J. Chromatogr., 1989, 465, 3, 378-385, https://doi.org/10.1016/S0021-9673(01)92675-5
. [all data]
Vassilaros, Kong, et al., 1982
Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L.,
Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices,
J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1
. [all data]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References
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