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, Reaction thermochemistry 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: 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
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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
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 |
Reaction thermochemistry data
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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
By formula: H2 + C13H9N = C13H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 75.3 | kJ/mol | Cm | Jackman and Packham, 1957 | liquid phase; solvent: bis-2-Ethoxyethyl ether |
Gas phase ion energetics 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 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
B - John E. Bartmess
View reactions leading to C13H9N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.8 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 972.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 940.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.896 ± 0.010 | LPES | Kokubo, Ando, et al., 2004 | B |
0.91 ± 0.10 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -20.3 kcal/mol; ΔSea =-1.5, taken as that of anthracene, from Kebarle and Chowdhury, 1987.9-aza-anthrancene; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.39 | CTS | Slifkin and Allison, 1967 | RDSH |
8.0 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
8.04 | CTS | Kinoshita, 1962 | RDSH |
7.8 | PI | Terenin, 1961 | RDSH |
8.13 ± 0.02 | PE | Maier, Muller, et al., 1975 | Vertical value; LLK |
7.85 | PE | Jongsma, Vermeer, et al., 1975 | Vertical value; LLK |
7.88 ± 0.02 | PE | Hush, Cheung, et al., 1975 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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]
Jackman and Packham, 1957
Jackman, L.M.; Packham, D.I.,
The experimental resonance energy of acridine,
Proc. Chem. Soc., London, 1957, 349-350. [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]
Kokubo, Ando, et al., 2004
Kokubo, S.; Ando, N.; Koyasu, K.; Mitsui, M.; Nakajima, A.,
Negative ion photoelectron spectroscopy of acridine molecular anion and its monohydrate,
J. Chem. Phys., 2004, 121, 22, 11112-11117, https://doi.org/10.1063/1.1818132
. [all data]
Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P.,
Electron Affinities of aza-substituted polycyclic aromatic hydrocarbons,
Can. J. Chem., 1989, 67, 10, 1628, https://doi.org/10.1139/v89-249
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C.,
Measurement of ionization potentials from contact charge transfer spectra,
Nature, 1967, 215, 949. [all data]
Farrell and Newton, 1966
Farrell, P.G.; Newton, J.,
Ionization potentials of primary aromatic amines and aza-hydrocarbons,
Tetrahedron Lett., 1966, 5517. [all data]
Kinoshita, 1962
Kinoshita, M.,
The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil,
Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Maier, Muller, et al., 1975
Maier, J.P.; Muller, J.-F.; Kubota, T.; Yamakawa, M.,
183. Ionisation energies and the electronic structures of the N-oxides of azanaphthalenes and azaanthracenes,
Helv. Chim. Acta, 1975, 58, 1641. [all data]
Jongsma, Vermeer, et al., 1975
Jongsma, C.; Vermeer, H.; Bickelhaupt, F.; Schafer, W.; Schweig, A.,
10-methyl-9-phosphaanthracene,
Tetrahedron, 1975, 31, 2931. [all data]
Hush, Cheung, et al., 1975
Hush, N.S.; Cheung, A.S.; Hilton, P.R.,
Binding energies of π- and "lone pair"-levels in mono- and diaza-phenanthrenes and anthracenes: an He(I) photoelectron spectroscopic study,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 385. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid EA Electron affinity IE (evaluated) Recommended ionization energy 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 ΔrH° Enthalpy of reaction at standard conditions 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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