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 ion energetics data
Go To: Top, 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
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 ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 ion energetics data, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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