3-Pyridinecarbonitrile
- Formula: C6H4N2
- Molecular weight: 104.1094
- IUPAC Standard InChI: InChI=1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H
- IUPAC Standard InChIKey: GZPHSAQLYPIAIN-UHFFFAOYSA-N
- CAS Registry Number: 100-54-9
- 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: Nicotinonitrile; Nicotinic acid nitrile; 3-Cyanopyridine; 3-Pyridylcarbonitrile; 3-Pyridinenitrile; 3-Azabenzonitrile; 3-Cyjanopirydyna; Nitryl kwasu nikotynowego; 3-Pyridyl cyanide; Pyridine-3-carbonitrile; NSC 17558
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
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.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 277.9 ± 2.0 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | ALS |
| ΔfH°gas | 265.4 | kJ/mol | N/A | Salley and Gray, 1951 | Value computed using ΔfHsolid° value of 193.3 kj/mol from Salley and Gray, 1951 and ΔsubH° value of 72.1 kj/mol from Bickerton, Pilcher, et al., 1984.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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°solid | 205.8 ± 0.9 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | |
| ΔfH°solid | 193.3 | kJ/mol | Ccb | Salley and Gray, 1951 | correction of Salley and Gray, 1948 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3138.5 ± 0.5 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | |
| ΔcH°solid | -3126.0 | kJ/mol | Ccb | Salley and Gray, 1951 | correction of Salley and Gray, 1948 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics 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 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.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 474.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 515.7 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 473. to 475. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
| Tboil | 479.85 | K | N/A | Ezhov, Golovko, et al., 1976 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 323.15 | K | N/A | Ezhov, Golovko, et al., 1976 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 323.65 | K | N/A | Waclawek and Hurwic, 1967 | Uncertainty assigned by TRC = 1. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 72.1 ± 1.8 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | ALS |
| ΔsubH° | 72.1 | kJ/mol | N/A | Bickerton, Pilcher, et al., 1984 | DRB |
| ΔsubH° | 72.1 ± 1.8 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 45. | 466. | A | Stephenson and Malanowski, 1987 | Based on data from 453. to 479. K. See also Dykyj, 1972.; AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 877.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 845.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.4 ± 0.1 | EI | Stefanovic and Grutzmacher, 1974 | LLK |
| 10.37 | PE | Ramsey and Walker, 1974 | Vertical value; LLK |
| 10.10 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: 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 | 1007. | 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, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5MS | 1012.7 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1875. | Shimoda, Shiratsuchi, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1012.0 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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.
Bickerton, Pilcher, et al., 1984
Bickerton, J.; Pilcher, G.; Al-Takhin, G.,
Enthalpies of combustion of the three aminopyridines and the three cyanopyridines,
J. Chem. Thermodyn., 1984, 16, 373-378. [all data]
Salley and Gray, 1951
Salley, D.J.; Gray, J.B.,
Heats of combustion of some organic nitrogen compounds,
J. Am. Chem. Soc., 1951, 73, 5925. [all data]
Salley and Gray, 1948
Salley, D.J.; Gray, J.B.,
Heats of combustion of some organic nitrogen compounds,
J. Am. Chem. Soc., 1948, 70, 2650-2653. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]
Ezhov, Golovko, et al., 1976
Ezhov, V.S.; Golovko, S.N.; Guseinov, E.M.,
Determination of the equilibrium characteristics of vapor-liquid and liquid-liquid systems applicable to products of the oxidative ammonolysis of toluene and alpha- and beta-picolines,
Khim.-Farm. Zh., 1976, 10, 10, 77. [all data]
Waclawek and Hurwic, 1967
Waclawek, Z.; Hurwic, J.,
Dipole moment and spectroscopic studies of the 1,3,5-trinitrobenzene complexes with some pyridine derivatives in nonpolar solvents,
Rocz. Chem., 1967, 41, 1993. [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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [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]
Stefanovic and Grutzmacher, 1974
Stefanovic, D.; Grutzmacher, H.F.,
The ionisation potential of some substituted pyridines,
Org. Mass Spectrom., 1974, 9, 1052. [all data]
Ramsey and Walker, 1974
Ramsey, B.G.; Walker, F.A.,
A linear relationship between substituted pyridine lone pair vertical ionization potentials and pKa,
J. Am. Chem. Soc., 1974, 96, 3314. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of aminopyridines and cyanopyridines,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 207. [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]
Andriamaharavo, 2014
Andriamaharavo, N.R.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]
Shimoda, Shiratsuchi, et al., 1996
Shimoda, M.; Shiratsuchi, H.; Nakada, Y.; Wu, Y.; Osajima, Y.,
Identification and sensory characterization of volatile flavor compounds in sesame seed oil,
J. Agric. Food Chem., 1996, 44, 12, 3909-3912, https://doi.org/10.1021/jf960115f
. [all data]
Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D.,
Volatile constituents of Perique tobacco,
Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) 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 ΔsubH° Enthalpy of sublimation 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.