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
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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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 65.46 ± 0.55 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 |
Reaction 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 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° | 18.0 | kcal/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) | 232.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 224.8 | kcal/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 |
IR Spectrum
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 113372 |
UV/Visible spectrum
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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: 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 | Zanker and Schmid, 1957 |
---|---|
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. 1228 |
Instrument | Zeiss PMQ II |
Melting point | 106 (form a); 110 (form b) |
Boiling point | 345.5 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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.
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]
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]
Zanker and Schmid, 1957
Zanker, V.; Schmid, W.,
Die tieftemperaturspektren der basen und kationen des pyridins, chinolins, acridins, 2.3-benzacridins und vorhersage der bandenlagen fur das 2.3;6.7-dibenzacridin,
Chem. Ber., 1957, 90, 2253-2265. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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