Acridine
- Formula: C13H9N
- Molecular weight: 179.2173
- IUPAC Standard InChIKey: DZBUGLKDJFMEHC-UHFFFAOYSA-N
- CAS Registry Number: 260-94-6
- 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: Acrydine; Benzo[b]quinoline; Dibenzo[b,e]pyridine; 10-Azaanthracene; 2,3-Benzoquinoline; 9-Azaanthracene; Akridin; UN 2713; NSC 3408; Acridine (Carbamazepine M)
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Gas phase thermochemistry data
Go To: Top, 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 273.9 ± 2.3 | kJ/mol | Ccr | Steele, Chirico, et al., 1989 |
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°solid | 179.4 ± 1.0 | kJ/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6581.3 ± 0.9 | kJ/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
ΔcH°solid | -6602.8 ± 6.7 | kJ/mol | Ccb | Willis, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -6601.5 ± 6.7 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 208.03 | J/mol*K | N/A | Steele, Chirico, et al., 1989 | DH |
S°solid,1 bar | 208.03 | J/mol*K | N/A | Steele, Chirico, et al., 1988 | DH |
S°solid,1 bar | 208.00 | J/mol*K | N/A | Steele, Chirico, et al., 1986 | DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
205.07 | 298.15 | Steele, Chirico, et al., 1989 | T = 5 to 500 K.; DH |
205.07 | 298.15 | Steele, Chirico, et al., 1988 | T = 5 to 500 K.; DH |
204.98 | 298.15 | Steele, Chirico, et al., 1986 | T = 6 to 450 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
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 | 618.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 383. ± 2. | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 383.24 | K | N/A | Steele, Chirico, et al., 1989, 2 | Uncertainty assigned by TRC = 0.01 K; extrapolation of T-1/f, IPTS-68; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 93. ± 3. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
71.5 ± 0.2 | 400. | IPM,EB | Steele, Chirico, et al., 1989 | Based on data from 383. to 637. K.; AC |
68.9 ± 0.1 | 440. | IPM,EB | Steele, Chirico, et al., 1989 | Based on data from 383. to 637. K.; AC |
66.4 ± 0.1 | 480. | IPM,EB | Steele, Chirico, et al., 1989 | Based on data from 383. to 637. K.; AC |
63.8 ± 0.1 | 520. | IPM,EB | Steele, Chirico, et al., 1989 | Based on data from 383. to 637. K.; AC |
61.3 ± 0.2 | 560. | IPM,EB | Steele, Chirico, et al., 1989 | Based on data from 383. to 637. K.; AC |
66.2 | 417. | A | Stephenson and Malanowski, 1987 | Based on data from 402. to 619. K. See also Stull, 1947.; AC |
62.9 | 465. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 621. K.; AC |
62.1 | 515. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 621. K.; AC |
61.5 | 595. | N/A | Sivaraman and Kobayashi, 1983 | Based on data from 423. to 621. K.; AC |
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 |
---|---|---|---|---|---|
402.6 to 619. | 4.84513 | 2805.33 | -39.349 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
86.0 | 430. | TGA | Lebedev, Chironov, et al., 1998 | AC |
89.5 ± 0.2 | 333. | C | Sabbah, Tabet, et al., 1994 | AC |
92.6 | 295. | N/A | Stephenson and Malanowski, 1987 | Based on data from 280. to 328. K.; AC |
92. ± 3. | 281.2 | V | McEachern, Sandoval, et al., 1975 | Hfusion=4.44±0.09 kcal/mol; ALS |
91.6 ± 2.5 | 290. | LE | McEachern, Sandoval, et al., 1975 | Based on data from 281. to 298. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.682 | 383.242 | N/A | Steele, Chirico, et al., 1989 | DH |
20.682 | 383.242 | N/A | Steele, Chirico, et al., 1988 | DH |
18.58 | 383.2 | DSC | McEachern, Sandoval, et al., 1975 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
53.97 | 383.242 | Steele, Chirico, et al., 1989 | DH |
53.97 | 383.242 | Steele, Chirico, et al., 1988 | DH |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-101 | 1800. | Maurer, 1990 | N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1819. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-52 | 1808. | Beernaert, 1979 | He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; Tend: 320. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 5 % Phenyl methyl siloxane | 1784. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1806. | Geldon, 1989 | Program: not specified |
Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1819. | Geldon, 1989 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 303.3 | Durlak, Biswas, et al., 1998 | 30. m/0.25 mm/0.25 μm, 15. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | SE-52 | 304.15 | Hasegawa, Usami, et al., 1990 | 2. K/min; Column length: 12. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 270. C |
Capillary | OV-101 | 303.18 | Blanco, Blanco, et al., 1989 | H2, 4. K/min; Column length: 25. m; Column diameter: 0.22 mm; Tstart: 50. C; Tend: 300. C |
Capillary | DB-5 | 303.99 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | SE-52 | 304.04 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Capillary | SE-52 | 301.94 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Capillary | SE-52 | 304.50 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-54 | 302.98 | Guillen, Iglesias, et al., 1992 | Program: not specified |
Capillary | SE-52 | 304.04 | Hasegawa, Usami, et al., 1990 | Column length: 12. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | OV-101 | 308.1 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of the five benzoquinolines,
J. Chem. Thermodyn., 1989, 21, 81-107. [all data]
Willis, 1947
Willis, J.B.,
The heats of combustion of some organic bases and their salts. The resonance energies of acridine and phenazine,
Trans. Faraday Soc., 1947, 43, 97-102. [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]
Steele, Chirico, et al., 1988
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.,
The thermodynamic properties of the five benzoquinolines,
NIPER Report, 1988, 337, 59p. [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]
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]
Steele, Chirico, et al., 1989, 2
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of the five benzoquinolines,
J. Chem. Thermodyn., 1989, 21, 81. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Sivaraman and Kobayashi, 1983
Sivaraman, Alwarappa; Kobayashi, Riki,
Vapor pressures and enthalpies of vaporization of thianthrene, acridine, and 9-methylanthracene at elevated temperatures,
The Journal of Chemical Thermodynamics, 1983, 15, 12, 1127-1135, https://doi.org/10.1016/0021-9614(83)90003-4
. [all data]
Lebedev, Chironov, et al., 1998
Lebedev, V.P.; Chironov, V.V.; Vorob'eva, V.P.; Matyushin, Yu.N.,
Energy of the dissociation of the bond N-NO in methylnitrosohydrazine,
Khim. Fiz., 1998, 17, 9, 54. [all data]
Sabbah, Tabet, et al., 1994
Sabbah, R.; Tabet, D.; Belaadi, S.,
Etude thermodynamique de l'acridine,
Thermochim. Acta, 1994, 247, 201-207. [all data]
McEachern, Sandoval, et al., 1975
McEachern, D.M.; Sandoval, O.; Iniguez, J.C.,
Vapor pressures, derived enthalpies of sublimation, enthalpies of fusion, and resonance energies of acridine and phenazine,
J. Chem. Thermodyn., 1975, 7, 299-306. [all data]
Maurer, 1990
Maurer, H.H.,
Detection of anticonvulsants and their metabolites in urine within a general unknown analysis procedure using computerized gas chromatography-mass spectrometry,
Arch. Toxicol., 1990, 64, 7, 554-561, https://doi.org/10.1007/BF01971834
. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Beernaert, 1979
Beernaert, H.,
Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons,
J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7
. [all data]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2
. [all data]
Geldon, 1989
Geldon, A.L.,
Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]
Durlak, Biswas, et al., 1998
Durlak, S.K.; Biswas, P.; Shi, J.; Bernhard, M.J.,
Characterization of polycyclic aromatic hydrocarbon particulate and gaseous emissions from polystyrene combustion,
Environ. Sci. Technol., 1998, 32, 15, 2301-2307, https://doi.org/10.1021/es9709031
. [all data]
Hasegawa, Usami, et al., 1990
Hasegawa, K.; Usami, S.; Higashide, A.,
Analysis of amino polycyclic aromatic hydrocarbons and polycyclic aromatic nitrogen heterocycles,
Nippon Kagaku Kaishi, 1990, 7, 777-788, https://doi.org/10.1246/nikkashi.1990.777
. [all data]
Blanco, Blanco, et al., 1989
Blanco, C.G.; Blanco, J.; Bermejo, J.; Guillen, M.D.,
Capillary gas chromatography of some polycyclic aromatic compounds on several stationary phases,
J. Chromatogr., 1989, 465, 3, 378-385, https://doi.org/10.1016/S0021-9673(01)92675-5
. [all data]
Vassilaros, Kong, et al., 1982
Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L.,
Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices,
J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1
. [all data]
Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M.,
Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons,
Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043
. [all data]
Guillen, Iglesias, et al., 1992
Guillen, M.D.; Iglesias, M.J.; Dominguez, A.; Blanco, C.G.,
Polynuclear aromatic hydrocarbon retention indices on SE-54 stationary phase of the volatile components of a coal tar pitch. Relationships between chromatographic retention and thermal reactivity,
J. Chromatogr., 1992, 591, 1-2, 287-295, https://doi.org/10.1016/0021-9673(92)80246-Q
. [all data]
Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H.,
Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 469-471, https://doi.org/10.1002/jhrc.1240090813
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) 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 ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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