Pyridine, 2,3-dimethyl-
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChIKey: HPYNZHMRTTWQTB-UHFFFAOYSA-N
- CAS Registry Number: 583-61-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 2,3-Lutidine; 2,3-Dimethylpyridine
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Phase change data
Go To: Top, Henry's Law 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 436.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 434.4 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 433.6 | K | N/A | Kyte, Jeffery, et al., 1960 | Uncertainty assigned by TRC = 1. K; TRC |
Tboil | 433.4 | K | N/A | Kyte, Jeffery, et al., 1960 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 430.75 | K | N/A | Hackmann, Wibaut, et al., 1943 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 258.35 | K | N/A | Kyte, Jeffery, et al., 1960 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 257.93 | K | N/A | Coulson, Cox, et al., 1959 | Uncertainty assigned by TRC = 0.03 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 258.57 | K | N/A | Chirico, Hossenlopp, et al., 1994 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 655.4 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 655.45 | K | N/A | Ambrose, Cox, et al., 1960 | Uncertainty assigned by TRC = 0.3 K; vis, PRT, IPTS-48, with decomp.; TRC |
Tc | 655.45 | K | N/A | Cox, 1960 | Uncertainty assigned by TRC = 1. K; measured by R. Townsend to be pub. later; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.41 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 12.4 ± 0.1 | kcal/mol | GS | Verevkin, 1999 | Based on data from 283. to 313. K.; AC |
ΔvapH° | 11.4 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 323. to 373. K.; AC |
ΔvapH° | 11.70 | kcal/mol | V | Cox, 1960 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.340 | 434.4 | N/A | Majer and Svoboda, 1985 | |
10.8 | 340. | EB | Steele, Chirico, et al., 1995 | Based on data from 328. to 476. K.; AC |
10.2 | 380. | EB | Steele, Chirico, et al., 1995 | Based on data from 328. to 476. K.; AC |
9.61 | 420. | EB | Steele, Chirico, et al., 1995 | Based on data from 328. to 476. K.; AC |
8.94 | 460. | EB | Steele, Chirico, et al., 1995 | Based on data from 328. to 476. K.; AC |
10.3 | 387. | A | Stephenson and Malanowski, 1987 | Based on data from 372. to 436. K. See also Kkykj and Repas, 1973.; AC |
11.2 | 313. | C | Majer, Svoboda, et al., 1985 | AC |
10.8 | 343. | C | Majer, Svoboda, et al., 1985 | AC |
10.4 | 368. | C | Majer, Svoboda, et al., 1985 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
313. to 368. | 15.53 | 0.2902 | 655.4 | Majer and Svoboda, 1985 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.222 | 258.6 | Chirico, Hossenlopp, et al., 1994, 2 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
47.350 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | DH |
258.565 | crystaline, I | liquid | Steele, Chirico, et al., 1986 | DH |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
140. | 700. | M | N/A |
Gas phase ion energetics data
Go To: Top, Phase change data, Henry's Law 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H9N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 229.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 221.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.85 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.1 | PE | Aue and Bowers, 1979 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Phase change data, Henry's Law 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | C78, Branched paraffin | 130. | 934.3 | Dallos, Sisak, et al., 2000 | He; Column length: 3.3 m |
Capillary | OV-101 | 110. | 941. | Golovnya, Kuz'menko, et al., 2000 | He; Phase thickness: 0.4 μm |
Packed | C78, Branched paraffin | 130. | 933.9 | Reddy, Dutoit, et al., 1992 | Chromosorb G HP; Column length: 3.3 m |
Packed | Apolane | 130. | 937. | Dutoit, 1991 | Column length: 3.7 m |
Capillary | OV-1 | 70. | 933. | Nabivach, 1989 | |
Capillary | OV-101 | 150. | 940. | Morishita, Morimoto, et al., 1986 | N2; Column length: 20. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 926. | Samusenko, Svetlova, et al., 1986 | 25. m/0.25 mm/0.156 μm, He |
Capillary | OV-101 | 80. | 924. | Samusenko, Svetlova, et al., 1986 | 35. m/0.25 mm/0.125 μm, He |
Capillary | OV-101 | 80. | 924. | Samusenko, Svetlova, et al., 1986 | 35. m/0.25 mm/0.125 μm, He |
Capillary | OV-101 | 80. | 925. | Samusenko, Svetlova, et al., 1986 | 35. m/0.25 mm/0.125 μm, He |
Capillary | OV-101 | 80. | 926. | Samusenko, Svetlova, et al., 1986 | 50. m/0.25 mm/0.125 μm, He |
Packed | Apiezon L | 130. | 963. | Shatts, Avots, et al., 1977 | He, Chromosorb W AW-DMCS; Column length: 2.4 m |
Packed | PMS-100 | 130. | 945. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 150. | 936. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 933. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-20M | 150. | 1424. | Morishita, Morimoto, et al., 1986 | N2; Column length: 20. m; Column diameter: 0.23 mm |
Packed | PEG-2000 | 150. | 1407. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1403. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1420. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1407. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1408. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1432. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Petro | 923.4 | Lu, Zhao, et al., 2004 | 50. m/0.2 mm/0.5 μm, 2. K/min; Tstart: 50. C; Tend: 220. C |
Capillary | HP-1 | 909. | Oh, Hartman, et al., 1992 | 50. m/0.32 mm/1.05 μm, He, 2. K/min, 260. C @ 10. min; Tstart: 40. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 952.2 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
Capillary | HP-5 | 945. | Kubec, Drhová, et al., 1999 | 30. m/0.25 mm/0.25 μm, N2, 40. C @ 3. min, 4. K/min, 240. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 953. | Li, Gao, et al., 2000 | Program: not specified |
Capillary | DB-1 | 919. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | DB-1 | 919. | Kawai, Ishida, et al., 1991 | 60. m/0.25 mm/0.25 μm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1358. | Umano, Hagi, et al., 1995 | He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
References
Go To: Top, Phase change data, Henry's Law 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.
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]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Kyte, Jeffery, et al., 1960
Kyte, C.T.; Jeffery, G.H.; Vogel, A.I.,
Physical Properties and Chem. Constitution XXVII. Pyridine Derivatives,
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Hackmann, Wibaut, et al., 1943
Hackmann, J.Th.; Wibaut, J.P.; Gitsels, H.P.L.,
Basic N compounds from cracked distillates of California petroleum,
Recl. Trav. Chim. Pays-Bas, 1943, 62, 229. [all data]
Coulson, Cox, et al., 1959
Coulson, E.A.; Cox, J.D.; Herington, E.F.G.; Martin, J.F.,
The Preparation and Physical Properties of the Pure Lutidines,
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Chirico, Hossenlopp, et al., 1994
Chirico, R.D.; Hossenlopp, I.A.; Gammon, B.E.; Knipmeyer, S.E.; Steele, W.V.,
Heat capacities of the six dimethylpyridines between the temperatures 10 K and 445 K and methyl-group rotational barriers in the solid state a,b,
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Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R.,
The critical temperatures of forty organic compounds,
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Cox, 1960
Cox, J.D.,
The second virial coefficients, latent heats of vaporization and heats of formation of the lutidines,
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Verevkin, 1999
Verevkin, Sergey P.,
Strain Effects in Phenyl-Substituted Methanes. Geminal Interaction between Phenyl and the Electron-Releasing Substituent in Benzylamines and Benzyl Alcohols,
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Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
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Steele, Chirico, et al., 1995
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E.,
Vapor pressures, high-temperature heat capacities, critical properties, derived thermodynamic functions, and barriers to methyl-group rotation, for the six dimethylpyridines,
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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
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Kkykj and Repas, 1973
Kkykj, J.; Repas, M.,
Petrochemia, 1973, 13, 179. [all data]
Majer, Svoboda, et al., 1985
Majer, V.; Svoboda, V.; Lencka, M.,
Enthalpies of vaporization and cohesive energies of dimethylpyridines and trimethylpyridines,
The Journal of Chemical Thermodynamics, 1985, 17, 4, 365-370, https://doi.org/10.1016/0021-9614(85)90133-8
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Chirico, Hossenlopp, et al., 1994, 2
Chirico, R.D.; Hossenlopp, I.A.; Gammon, B.E.; Knipmeyer, S.E.; Steele, W.V.,
Heat capacities of the six dimethylpyridines between the temperatures 10 K and 445 K and methyl-group rotational barriers in the solid state a,b,
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Steele, Chirico, et al., 1986
Steele, W.V.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Strube, M.M.,
Thermochemical and thermophysical properties of organic nitrogen compounds found in fossil materials,
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Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
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Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E.,
Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups,
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Golovnya, Kuz'menko, et al., 2000
Golovnya, R.V.; Kuz'menko, T.E.; Krikunova, N.I.,
The influence of alkyl substituents on the chromatographic indicator of self-association of N-containing heterocyclic compounds,
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Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz.,
Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups,
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Dutoit, 1991
Dutoit, J.,
Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases,
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Nabivach, 1989
Nabivach, V.M.,
Calculation of gas chromatographic retention indices for alkylpyridines from their structural characteristics,
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Morishita, Morimoto, et al., 1986
Morishita, F.; Morimoto, S.; Kojima, T.,
Prediction of molecular structures of aza-arenes by retention indices and fluorescence spectra,
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Samusenko, Svetlova, et al., 1986
Samusenko, A.L.; Svetlova, N.I.; Golovnya, R.V.,
Reproducible and durable glass capillary columns with hydrogenated apiezon-l and OV-101 for the analysis of polar substances,
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Shatts, Avots, et al., 1977
Shatts, V.D.; Avots, A.A.; Belikov, V.A.,
Retention indices of alkylpyridines,
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Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
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Lu, Zhao, et al., 2004
Lu, X.; Zhao, M.; Kong, H.; Cai, J.; Wu, J.; Wu, M.; Hua, R.; Liu, J.; Xu, G.,
Characterization of cigarette smoke condensates by comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry (GC x GC/TOFMS) Part 2: Basic fraction,
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Oh, Hartman, et al., 1992
Oh, Y.-C.; Hartman, T.G.; Ho, C.-T.,
Volatile compounds generated from the Maillard reaction of pro-gly, gly-pro, and a mixture of glycine and proline with glucose,
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Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D.,
Volatile constituents of Perique tobacco,
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Kubec, Drhová, et al., 1999
Kubec, R.; Drhová, V.; Velísek, J.,
Volatile compounds thermally generated from S-propylcysteine and S-propylcysteine sulfoxide - aroma precursors of Allium vegetables,
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Using improved BP neural network in predicting GC retention indices,
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Flavor components of dried squid,
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Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T.,
Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system,
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Notes
Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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