2,2'-Bipyridine

• Formula: C₁₀H₈N₂
• Molecular weight: 156.1839
• IUPAC Standard InChI: InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H Copy

  
• IUPAC Standard InChIKey: ROFVEXUMMXZLPA-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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Gas 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

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

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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Enthalpy of fusion

Gas phase ion energetics 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:
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

Ionization energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

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]

Faour and Akasheh, 1985
Faour, M.; Akasheh, T.S., Heat of combustion of some N-heterocycle compounds. Part 1, J. Chem. Soc. Perkin Trans. 2, 1985, 811-713. [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]

Sevastyanova, Suvorov, et al., 1990
Sevastyanova, T.N.; Suvorov, V.; Konysheva, I.I., Thermodynamics of vaporisation of 2,2'-bipyridine and some binary systems with it in Vses. Konf. Term. Org. Soedin. 6th, Minsk, p 33, 1990. [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]

Emmenegger, 1996
Emmenegger, Franzpeter, The Complex of Co(2,2,6,6-tetramethyl-3,5-heptanedionate) ₂ with 2,2'-Bipyridine. Its Formation in the Gas Phase and in Solution, Inorg. Chem., 1996, 35, 20, 5931-5934, https://doi.org/10.1021/ic9605130 . [all data]

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]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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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