Pyridine
- Formula: C5H5N
- Molecular weight: 79.0999
- IUPAC Standard InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N
- CAS Registry Number: 110-86-1
- 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. - Isotopologues:
- Other names: Azabenzene; Azine; NCI-C55301; Piridina; Pirydyna; Pyridin; Rcra waste number U196; UN 1282; Pyr; CP 32; NSC 406123
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | 33.50 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔfH°gas | 33.61 ± 0.36 | kcal/mol | Cm | Andon, Cox, et al., 1957 | ALS |
ΔfH°gas | 33.63 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°gas | 26.31 | kcal/mol | N/A | Constam and White, 1903 | Value computed using ΔfHliquid° value of 69.9 kj/mol from Constam and White, 1903 and ΔvapH° value of 40.2 kj/mol from Hubbard, Frow, et al., 1961.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 23.89 ± 0.12 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔfH°liquid | 23.95 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔfH°liquid | 16.7 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -651.3 | kcal/mol | Ccb | Strepikheev, Baranov, et al., 1962 | ALS |
ΔcH°liquid | -664.95 ± 0.10 | kcal/mol | Ccb | Hubbard, Frow, et al., 1961 | ALS |
ΔcH°liquid | -665.00 ± 0.36 | kcal/mol | Ccb | Cox, Challoner, et al., 1954 | ALS |
ΔcH°liquid | -659.2 | kcal/mol | Ccb | Constam and White, 1903 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 42.519 | cal/mol*K | N/A | McCullough, Douslin, et al., 1957 | DH |
S°liquid | 42.81 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 50.04 J/mol*K.; DH |
S°liquid | 50.289 | cal/mol*K | N/A | Pearce and Bakke, 1936 | Extrapolation below 90 K, 89.33 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.22 | 293. | Rastorguev and Ganiev, 1967 | T = 293 to 353 K.; DH |
31.8 | 298.15 | Hubbard, Frow, et al., 1961 | DH |
35.11 | 332. | Swietoslawski and Zielenkiewicz, 1958 | Mean value 22 to 96°C.; DH |
31.721 | 298.15 | McCullough, Douslin, et al., 1957 | T = 10 to 350 K.; DH |
32.249 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
31.859 | 298.1 | Pearce and Bakke, 1936 | T = 90 to 298 K. Value is unsmoothed experimental datum.; DH |
30.90 | 289. | Radulescu and Jula, 1934 | DH |
32.349 | 273.4 | Swietoslawski, Tybicka, et al., 1931 | DH |
32.41 | 290. | Swietoslawski, Tybicka, et al., 1931, 2 | DH |
30.911 | 294. | Mathews, Krause, et al., 1917 | DH |
31.19 | 283. | Bramley, 1916 | Mean value, 0 to 20°C.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 388.5 ± 0.6 | K | AVG | N/A | Average of 80 out of 84 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 232. ± 2. | K | AVG | N/A | Average of 26 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 231.48 | K | N/A | Helm, Lanum, et al., 1958 | Uncertainty assigned by TRC = 0.03 K; measured in calorimeter at USBM, Bartlesville, OK; TRC |
Ttriple | 231.480 | K | N/A | McCullough, Douslin, et al., 1957, 2 | Uncertainty assigned by TRC = 0.05 K; by extrapolation of 1/f to zero; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 619. ± 2. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 55.86 | atm | N/A | Brunner, 1987 | Uncertainty assigned by TRC = 0.0558 atm; Visual, optical cell 30cm high. P transducer cal. vs PB.; TRC |
Pc | 55.66 | atm | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1.020 atm; TRC |
Pc | 60.000 | atm | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.253 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.005 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.63 ± 0.06 | kcal/mol | AVG | N/A | Average of 10 out of 11 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.387 | 388.4 | N/A | Majer and Svoboda, 1985 | |
9.39 | 324. | N/A | Ukraintseva, Soldatov, et al., 1997 | Based on data from 289. to 358. K.; AC |
8.99 | 354. | N/A | Blanco, Beltran, et al., 1994 | Based on data from 346. to 362. K.; AC |
9.54 | 310. | EB | Lencka, 1990 | Based on data from 295. to 388. K.; AC |
9.49 | 311. | A | Stephenson and Malanowski, 1987 | Based on data from 296. to 353. K.; AC |
8.91 | 363. | A | Stephenson and Malanowski, 1987 | Based on data from 348. to 434. K.; AC |
8.37 | 446. | A | Stephenson and Malanowski, 1987 | Based on data from 431. to 558. K.; AC |
8.13 | 567. | A | Stephenson and Malanowski, 1987 | Based on data from 552. to 620. K.; AC |
8.99 | 355. | EB | Stephenson and Malanowski, 1987 | Based on data from 340. to 426. K. See also McCullough, Douslin, et al., 1957.; AC |
9.46 | 313. | C | Michou-Saucet, Jose, et al., 1986 | Based on data from 298. to 333. K.; AC |
9.42 | 313. | C | Majer, Svoboda, et al., 1984 | AC |
9.20 | 328. | C | Majer, Svoboda, et al., 1984 | AC |
9.01 | 343. | C | Majer, Svoboda, et al., 1984 | AC |
8.68 | 368. | N/A | Majer, Svoboda, et al., 1984 | AC |
8.96 ± 0.02 | 346. | C | McCullough, Douslin, et al., 1957 | AC |
8.70 ± 0.02 | 366. | C | McCullough, Douslin, et al., 1957 | AC |
8.39 ± 0.02 | 388. | C | McCullough, Douslin, et al., 1957 | AC |
9.18 | 335. | MG | Herington and Martin, 1953 | Based on data from 320. to 388. K.; AC |
10.6 | 273. | N/A | Meulen and Mann, 1931 | Based on data from 258. to 389. K.; 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)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 388. | 13.25 | 0.2536 | 620. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
340.5 to 426.04 | 4.15701 | 1371.358 | -58.496 | McCullough, Douslin, et al., 1957 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.9786 | 231.49 | McCullough, Douslin, et al., 1957 | Includes energy of anomaly at about 210 K.; DH |
1.98 | 231.5 | Domalski and Hearing, 1996 | AC |
1.977 | 231.1 | Parks, Todd, et al., 1936 | DH |
0.7409 | 230.38 | Pearce and Bakke, 1936 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.547 | 231.49 | McCullough, Douslin, et al., 1957 | Includes; DH |
8.554 | 231.1 | Parks, Todd, et al., 1936 | DH |
3.217 | 230.38 | Pearce and Bakke, 1936 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C5H4N- + =
By formula: C5H4N- + H+ = C5H5N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 389.9 ± 2.0 | kcal/mol | IMRE | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 391.0 ± 2.5 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.7 ± 2.0 | kcal/mol | TDEq | Meot-ner and Kafafi, 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
ΔrG° | 384.0 ± 3.0 | kcal/mol | IMRB | DePuy, Kass, et al., 1988 | gas phase; Comparable to water in acidity; B |
ΔrG° | <376.3 ± 2.0 | kcal/mol | IMRB | Bruins, Ferrer-Correia, et al., 1978 | gas phase; O- deprotonates; B |
By formula: C5H6N+ + C5H5N = (C5H6N+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.2 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 24.6 | kcal/mol | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrH° | 26.3 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrH° | 23.7 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 28.2 | cal/mol*K | PHPMS | Meot-Ner M. and Sieck, 1983 | gas phase; M |
ΔrS° | 32.1 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
ΔrS° | 28. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1979 | gas phase; M |
By formula: C5H5N + 3H2 = C5H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -46.31 ± 0.18 | kcal/mol | Eqk | Hales and Herington, 1957 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -48.32 ± 0.18 kcal/mol; At 400-550 K; ALS |
ΔrH° | -46.12 ± 0.50 | kcal/mol | Eqk | Burrows and King, 1935 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -45.00 kcal/mol; At 423-443 K; ALS |
By formula: Cl- + C5H5N = (Cl- • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.7 ± 2.0 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.7 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 6.8 ± 2.6 | kcal/mol | TDAs | Hiraoka, Mizuse, et al., 1988 | gas phase; B |
By formula: (C5H6N+ • 2C5H5N) + C5H5N = (C5H6N+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 37.9 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
By formula: Li+ + C5H5N = (Li+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.2 ± 3.5 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 44. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: K+ + C5H5N = (K+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.6 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
ΔrH° | 20.7 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 18.6 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; M |
By formula: (Ag+ • 2C5H5N) + C5H5N = (Ag+ • 3C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16.7 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28.0 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Ag+ • 3C5H5N) + C5H5N = (Ag+ • 4C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.9 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 40.3 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: (Cl- • C5H5N) + C5H5N = (Cl- • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.7 | kcal/mol | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.6 | cal/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1988 | gas phase; M |
By formula: (C5H6N+ • C5H5N) + C5H5N = (C5H6N+ • 2C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.6 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.7 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; M |
By formula: H2O3- + C5H5N + H2O = C5H7NO3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+ = C5H5NO2-
By formula: O2- + C5H5N = C5H5NO2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.7 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+ = C5H5N2O-
By formula: NO- + C5H5N = C5H5N2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.6 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
3 + = 3 + KClO3
By formula: 3C5H5NO + ClK = 3C5H5N + KClO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.2 ± 2.4 | kcal/mol | Cm | Shaofeng and Pilcher, 1988 | solid phase; ALS |
3 + = 3 + KBrO3
By formula: 3C5H5NO + BrK = 3C5H5N + KBrO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.0 ± 2.3 | kcal/mol | Cm | Shaofeng and Pilcher, 1988 | solid phase; ALS |
By formula: Fe+ + C5H5N = (Fe+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.4 ± 2.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cr+ + C5H5N = (Cr+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.1 ± 2.8 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ti+ + C5H5N = (Ti+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.9 ± 2.3 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mn+ + C5H5N = (Mn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.4 ± 2.1 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Sc+ + C5H5N = (Sc+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.3 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Mg+ + C5H5N = (Mg+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.8 ± 1.6 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: V+ + C5H5N = (V+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.2 ± 3.2 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Ni+ + C5H5N = (Ni+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.9 ± 3.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Al+ + C5H5N = (Al+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.5 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Zn+ + C5H5N = (Zn+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 1.7 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Co+ + C5H5N = (Co+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 3.0 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Cu+ + C5H5N = (Cu+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.7 ± 2.5 | kcal/mol | CIDT | Rodgers, Stanley, et al., 2000 | RCD |
By formula: Na+ + C5H5N = (Na+ • C5H5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.3 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2000 | RCD |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
- GAS (15 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-250 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- VAPOR (0.5 MICROLITER AT 150 C); NICOLET FTIR; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 CM-1 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, UV/Visible spectrum, 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
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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- 79 |
NIST MS number | 227742 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | missing citation |
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Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 1112 |
Instrument | Zeiss PMQII |
Melting point | -41.6 |
Boiling point | 115.2 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hubbard, Frow, et al., 1961
Hubbard, W.N.; Frow, F.R.; Waddington, G.,
The heats of combustion and formation of pyridine and hippuric acid,
J. Phys. Chem., 1961, 65, 1326-1328. [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]
Constam and White, 1903
Constam, E.J.; White, J.,
Physico-chemical investigations in the pyridine series,
Am. Chem. J., 1903, 29, 1-49. [all data]
Strepikheev, Baranov, et al., 1962
Strepikheev, Yu.A.; Baranov, Yu.I.; Burmistrova, O.A.,
Determination of the heats of combustion and the heat capacities of several mono- and di-isocyanates,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1962, 5, 387-390. [all data]
McCullough, Douslin, et al., 1957
McCullough, J.P.; Douslin, D.R.; Messerly, J.F.; Hossenlopp, I.A.; Kincheloe, T.C.; Waddington, G.,
Pyridine: experimental and calculated chemical thermodynamic properties between 0 and 1500 K., a revised vibrational assignment,
J. Am. Chem. Soc., 1957, 79, 4289-4295. [all data]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds,
J. Am. Chem. Soc., 1936, 58, 398-401. [all data]
Pearce and Bakke, 1936
Pearce, J.N.; Bakke, H.M.,
The heat capacity and the free energy of formation of pyridine,
Proc. Iowa Acad. Sci., 1936, 43, 171-174. [all data]
Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A.,
Study of the heat capacity of selected solvents,
Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]
Swietoslawski and Zielenkiewicz, 1958
Swietoslawski, W.; Zielenkiewicz, A.,
Mean specific heat of some ternary azeotropes,
Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1958, 6, 365-366. [all data]
Radulescu and Jula, 1934
Radulescu, D.; Jula, O.,
Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen,
Z. Phys. Chem., 1934, B26, 390-393. [all data]
Swietoslawski, Tybicka, et al., 1931
Swietoslawski, W.; Tybicka, S.; Solodkowska, W.,
Sur un microcalorimetre adiabatique, adapte aux mesures de la chaleur specifique de substances solides et liquides,
Bull. Int. Acad. Pol. Sci. Lett. Cl. Sci. Math Nat. Ser A, 1931, 1931, 322-335. [all data]
Swietoslawski, Tybicka, et al., 1931, 2
Swietoslawski, W.; Tybicka, S.; Solodkowska, W.,
Sur un microcalorimetre adiabatique, adapte aux mesures de la chaleur specifique de substances solides et liquides,
Rocz. Chem., 1931, 11, 65-77. [all data]
Mathews, Krause, et al., 1917
Mathews, J.H.; Krause, E.L.; Bohnson, B.L.,
a contribution to the thermal chemistry of pyridine,
J. Am. Chem. Soc., 1917, 39, 398-413. [all data]
Bramley, 1916
Bramley, A.,
The study of binary mixtures. Part IV. Heats of reaction and specific heats,
J. Chem. Soc. (London), 1916, 109, 496-515. [all data]
Helm, Lanum, et al., 1958
Helm, R.V.; Lanum, W.J.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Pyrrole, Pyrrolidine, Pyridine and 2-Methylpyridine,
J. Phys. Chem., 1958, 62, 858. [all data]
McCullough, Douslin, et al., 1957, 2
McCullough, J.P.; Douslin, D.R.; Messerly, J.F.; Hossenlopp, I.A.; Kincheloe, T.C.; Waddington, G.,
Pyridine: Experimental and Calculated Chemical Thermodynamic Prop- erties Between 0 and 1500 K; A Revised Vibrational Assignment,
J. Am. Chem. Soc., 1957, 79, 4289. [all data]
Brunner, 1987
Brunner, E.,
Fluid mixtures at high pressures VI. Phase separation and critical phenomina in 18 binary mixtures containing either pyridine or ethanoic acid,
J. Chem. Thermodyn., 1987, 19, 823. [all data]
Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P.,
Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds,
J. Chem. Eng. Data, 1956, 1, 50. [all data]
Herz and Neukirch, 1923
Herz, W.; Neukirch, E.,
On Knowldge of the Critical State,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [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]
Ukraintseva, Soldatov, et al., 1997
Ukraintseva, E.A.; Soldatov, D.V.; Dyadin, Yu.A.,
Pyridine vapor pressure and thermodynamic parameters of clathrate and complex formation in the pyridine-zinc nitrate system,
Zh. Neorg. Khim., 1997, 42, 2, 283. [all data]
Blanco, Beltran, et al., 1994
Blanco, Beatriz; Beltran, Sagrario; Cabezas, Jose Luis; Coca, Jose,
Vapor-liquid equilibria of coal-derived liquids. 3. Binary systems with tetralin at 200 mm mercury,
J. Chem. Eng. Data, 1994, 39, 1, 23-26, https://doi.org/10.1021/je00013a007
. [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]
Michou-Saucet, Jose, et al., 1986
Michou-Saucet, Marie-Annie; Jose, Jacques; Michou-Saucet, Christian,
Equilibre liquide-vapeur isotherme des systemes pyridine-n-hexane et pyridine-n-heptane,
Thermochimica Acta, 1986, 102, 271-279, https://doi.org/10.1016/0040-6031(86)85335-7
. [all data]
Majer, Svoboda, et al., 1984
Majer, V.; Svoboda, V.; Lencka, M.,
Enthalpies of vaporization and cohesive energies of pyridine and isomeric methylpyridines,
J. Chem. Thermodyn., 1984, 16, 1019-1024. [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]
Meulen and Mann, 1931
Meulen, P.A. van der.; Mann, Russell F.,
THE VAPOR PRESSURE OF PYRIDINE,
J. Am. Chem. Soc., 1931, 53, 2, 451-453, https://doi.org/10.1021/ja01353a006
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G.,
Regioselectivity of pyridine deprotonation in the gas phase,
J. Org. Chem., 2007, 72, 5, 1645-1651, https://doi.org/10.1021/jo062117x
. [all data]
Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A.,
Carbon Acidities of Aromatic Compounds,
J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [all data]
DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P.,
Formation and Reactions of Heteroaromatic Anions in the Gas Phase,
J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001
. [all data]
Bruins, Ferrer-Correia, et al., 1978
Bruins, A.P.; Ferrer-Correia, A.J.; Harrison, A.G.; Jennings, K.R.; Mithcum, R.K.,
Negative ion chemical ionization mass spectrometry of some aromatic compounds using O-. as the reagent ion,
Adv. Mass Spectrom., 1978, 7, 355. [all data]
Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M.,
Intermolecular Forces in Organic Clusters,
J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024
. [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]
Holland and Castleman, 1982
Holland, P.M.; Castleman, A.W.,
The Thermochemical Properties of Gas - Phase Transition Metal Ion Complexes,
J. Chem. Phys., 1982, 76, 8, 4195, https://doi.org/10.1063/1.443497
. [all data]
Meot-Ner (Mautner), 1979
Meot-Ner (Mautner), M.,
Ion Thermochemistry of Low Volatility Compounds in the Gas Phase. II. Intrinsic Basicities and Hydrogen Bonded Dimers of Nitrogen Heterocyclics and Nucleic Bases,
J. Am. Chem. Soc., 1979, 101, 9, 2396, https://doi.org/10.1021/ja00503a027
. [all data]
Hales and Herington, 1957
Hales, J.L.; Herington, E.F.G.,
Equilibrium between pyridine and piperidine,
Trans. Faraday Soc., 1957, 53, 616-622. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Burrows and King, 1935
Burrows, G.H.; King, L.A., Jr.,
The free energy change that accompanies hydrogenation of pyridine to piperidine,
J. Am. Chem. Soc., 1935, 57, 1789-1791. [all data]
Hiraoka, Mizuse, et al., 1988
Hiraoka, K.; Mizuse, S.; Yamabe, S.,
Determination of the Stabilities and Structures of X-(C6H6) Clusters (X = Cl, Br, and I),
Chem. Phys. Lett., 1988, 147, 2-3, 174, https://doi.org/10.1016/0009-2614(88)85078-4
. [all data]
Amunugama and Rodgers, 2000
Amunugama, R.; Rodgers, M.T.,
Absolute Alkali Metal Ion Binding Affinities of Several Azines Determined by Threshold Collision-Induced Dissociation and Ab Initio Theory,
Int. J. Mass Spectrom., 2000, 195/196, 439, https://doi.org/10.1016/S1387-3806(99)00145-1
. [all data]
Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050
. [all data]
Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013
. [all data]
Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P.,
Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M,
J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011
. [all data]
Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H.,
Microsolvation of small anions by aromatic molecules: An exploratory study,
J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750
. [all data]
Shaofeng and Pilcher, 1988
Shaofeng, L.; Pilcher, G.,
Enthalpy of formation of pyridine-N-oxide: the dissociation enthalpy of the (N-O) bond,
J. Chem. Thermodyn., 1988, 20, 463-465. [all data]
Rodgers, Stanley, et al., 2000
Rodgers, M.T.; Stanley, J.R.; Amunugama, R.,
Periodic Trends in the Binding of Metal Ions to Pyridine Studied by Threshold Collision-Induced Dissociation and Density Functional Theory,
J. Am. Chem. Soc., 2000, 122, 44, 10969, https://doi.org/10.1021/ja0027923
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume 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 ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions 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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