2,6-Lutidine
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChIKey: OISVCGZHLKNMSJ-UHFFFAOYSA-N
- CAS Registry Number: 108-48-5
- 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: Pyridine, 2,6-dimethyl-; α,α'-Dimethylpyridine; α,α'-Lutidine; 2,6-Dimethylpyridine; 2,6-Dimethypyridine; α,α'-Lutidin; NSC 2155
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 58.7 | kJ/mol | N/A | Cox and Gundry, 1958 | Value computed using ΔfHliquid° value of 12.6 kj/mol from Cox and Gundry, 1958 and ΔvapH° value of 46.06 kj/mol from missing citation.; DRB |
ΔfH°gas | 56.1 ± 1.5 | kJ/mol | Cm | Andon, Cox, et al., 1957 | ALS |
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 as indicated in comments:
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 |
---|---|---|---|---|---|
ΔfH°liquid | 12.6 | kJ/mol | Ccb | Cox and Gundry, 1958 | see Cox, Challoner, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4053.5 | kJ/mol | Ccb | Cox and Gundry, 1958 | see Cox, Challoner, et al., 1954; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 244.24 | J/mol*K | N/A | Steele, Chirico, et al., 1986 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
185.17 | 298.15 | Steele, Chirico, et al., 1986 | T = 10 to 440 K.; DH |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 417. ± 1. | K | AVG | N/A | Average of 22 out of 26 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 268. ± 7. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 267.03 | K | N/A | Chirico, Hossenlopp, et al., 1994 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 623.8 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 623.75 | K | N/A | Ambrose and Grant, 1957 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 45.38 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 45.9 ± 2.4 | kJ/mol | CGC | Lipkind and Chickos, 2009 | Based on data from 342. to 373. K.; AC |
ΔvapH° | 45.3 | kJ/mol | N/A | Ben-makhlouf-Hakem, Ait-Kaci, et al., 2005 | Based on data from 263. to 353. K.; AC |
ΔvapH° | 46.4 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 323. to 373. K.; AC |
ΔvapH° | 46.062 | kJ/mol | V | Andon, Cox, et al., 1957 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
37.46 | 417.3 | N/A | Majer and Svoboda, 1985 | |
43.7 | 330. | N/A | Sakoguchi, Ueoka, et al., 1995 | Based on data from 288. to 373. K.; AC |
43.9 | 320. | EB | Steele, Chirico, et al., 1995 | Based on data from 315. to 457. K.; AC |
41.4 | 360. | EB | Steele, Chirico, et al., 1995 | Based on data from 315. to 457. K.; AC |
38.8 | 400. | EB | Steele, Chirico, et al., 1995 | Based on data from 315. to 457. K.; AC |
36.0 | 440. | EB | Steele, Chirico, et al., 1995 | Based on data from 315. to 457. K.; AC |
45.0 | 310. | EB | Lencka, 1990 | Based on data from 295. to 417. K.; AC |
41.6 | 367. | A,MG | Stephenson and Malanowski, 1987 | Based on data from 352. to 418. K. See also Herington and Martin, 1953.; AC |
46.1 | 282. | MM | Wisniewska, Lencka, et al., 1986 | Based on data from 267. to 358. K.; AC |
44.4 | 313. | C | Majer, Svoboda, et al., 1985 | AC |
42.5 | 343. | C | Majer, Svoboda, et al., 1985 | AC |
40.8 | 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)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
313. to 368. | 63.35 | 0.2961 | 623.8 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
352.44 to 417.5 | 4.18785 | 1474.239 | -64.685 | Herington and Martin, 1953, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.04 | 267.1 | Chirico, Hossenlopp, et al., 1994, 2 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
35.816 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1986 | DH |
267.033 | 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 |
---|---|---|---|
94. | 7300. | M | N/A |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Ion clustering data, Mass spectrum (electron ionization), 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
L - 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 |
---|---|---|---|---|---|
IE (evaluated) | 8.86 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 963.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 931.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.87 | PE | Utsunomiya, Kobayashi, et al., 1978 | LLK |
9.23 ± 0.05 | EI | Distefano, Foffani, et al., 1971 | LLK |
9.23 | EI | Distefano, Foffani, et al., 1971, 2 | LLK |
8.85 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.90 ± 0.05 | PE | Heilbronner, Hornung, et al., 1972 | Vertical value; LLK |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C7H10N+ + C7H9N = (C7H10N+ • C7H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 97.5 | kJ/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 139. | J/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 652 |
NIST MS number | 227861 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Cox and Gundry, 1958
Cox, J.D.; Gundry, H.A.,
Heats of combustion. Part II. The six lutidines,
J. Chem. Soc., 1958, 1019-1022. [all data]
Andon, Cox, et al., 1957
Andon, R.J.L.; Cox, J.D.; Herington, E.F.G.; Martin, J.F.,
The second virial coefficients of pyridine and benzene, and certain of their methyl homologues,
Trans. Faraday Soc., 1957, 53, 1074. [all data]
Cox, Challoner, et al., 1954
Cox, J.D.; Challoner, A.R.; Meetham, A.R.,
The heats of combustion of pyridine and certain of its derivatives,
J. Chem. Soc., 1954, 265-271. [all data]
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,
NIPER Report, 1986, 188, 112p. [all data]
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,
J. Chem. Thermodyn., 1994, 26, 11, 1187, https://doi.org/10.1006/jcht.1994.1138
. [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]
Ambrose and Grant, 1957
Ambrose, D.; Grant, D.G.,
The Critical Temperatures of Some Hydrocarbons and Pyridine Bases,
Trans. Faraday Soc., 1957, 53, 771. [all data]
Lipkind and Chickos, 2009
Lipkind, Dmitri; Chickos, James S.,
An examination of the vaporization enthalpies and vapor pressures of pyrazine, pyrimidine, pyridazine, and 1,3,5-triazine,
Struct Chem, 2009, 20, 1, 49-58, https://doi.org/10.1007/s11224-008-9389-5
. [all data]
Ben-makhlouf-Hakem, Ait-Kaci, et al., 2005
Ben-makhlouf-Hakem, Hamama; Ait-Kaci, Ahmed; Jose, Jacques,
Vapour pressures and excess functions of (3,5; 2,6)dimethylpyridine+n-hexane, n-heptane and n-octane measurement and prediction,
Fluid Phase Equilibria, 2005, 232, 1-2, 189-206, https://doi.org/10.1016/j.fluid.2005.03.028
. [all data]
Chickos, Hosseini, et al., 1995
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,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Sakoguchi, Ueoka, et al., 1995
Sakoguchi, Akihiro; Ueoka, Ryuichi; Kato, Yasuo; Arai, Yasuhiko,
Vapor Pressures of Alkylpyridines and Alkylpyrazines.,
KAGAKU KOGAKU RONBUNSHU, 1995, 21, 1, 219-223, https://doi.org/10.1252/kakoronbunshu.21.219
. [all data]
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,
The Journal of Chemical Thermodynamics, 1995, 27, 3, 311-334, https://doi.org/10.1006/jcht.1995.0030
. [all data]
Lencka, 1990
Lencka, Malgorzata,
Measurements of the vapour pressures of pyridine, 2-methylpyridine, 2,4-dimethylpyridine, 2,6-dimethylpyridine, and 2,4,6-trimethylpyridine from 0.1 kPa to atmospheric pressure using a modified Swietoslawski ebulliometer,
The Journal of Chemical Thermodynamics, 1990, 22, 5, 473-480, https://doi.org/10.1016/0021-9614(90)90139-H
. [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]
Herington and Martin, 1953
Herington, E.F.G.; Martin, J.F.,
Vapour pressures of pyridine and its homologues,
Trans. Faraday Soc., 1953, 49, 154, https://doi.org/10.1039/tf9534900154
. [all data]
Wisniewska, Lencka, et al., 1986
Wisniewska, Barbara; Lencka, Malgorzata; Rogalski, Marek,
Vapour pressures of 2,4-, 2,6-, and 3,5-dimethylpyridine at temperatures from 267 to 360 K,
The Journal of Chemical Thermodynamics, 1986, 18, 8, 703-708, https://doi.org/10.1016/0021-9614(86)90102-3
. [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
. [all data]
Herington and Martin, 1953, 2
Herington, E.F.G.; Martin, J.F.,
Vapour Pressures of Pyridine and its Homologues,
Trans. Faraday Soc., 1953, 49, 154-162, https://doi.org/10.1039/tf9534900154
. [all data]
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,
The Journal of Chemical Thermodynamics, 1994, 26, 11, 1187-1218, https://doi.org/10.1006/jcht.1994.1138
. [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]
Utsunomiya, Kobayashi, et al., 1978
Utsunomiya, C.; Kobayashi, T.; Nagakura, S.,
Photoelectron angular distribution measurements for some pyridines,
Bull. Chem. Soc. Jpn., 1978, 451, 3482. [all data]
Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom,
Adv. Mass Spectrom., 1971, 5, 696. [all data]
Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives,
Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F.,
31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines,
Helv. Chim. Acta, 1972, 55, 289. [all data]
Meot-Ner M. and Sieck, 1983
Meot-Ner M.; Sieck, L.W.,
The Ionic Hydrogen Bond. 1. Sterically Hindered Bonds. Solvation and Clustering of Sterically Hindered Amines and Pyridines,
J. Am. Chem. Soc., 1983, 105, 10, 2956, https://doi.org/10.1021/ja00348a005
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions 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 ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions 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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