Menadione
- Formula: C11H8O2
- Molecular weight: 172.1800
- IUPAC Standard InChI: InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
- IUPAC Standard InChIKey: MJVAVZPDRWSRRC-UHFFFAOYSA-N
- CAS Registry Number: 58-27-5
- 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: 1,4-Naphthalenedione, 2-methyl-; 1,4-Naphthoquinone, 2-methyl-; Aquakay; Aquinone; Hemodal; K-Thrombyl; K-Vitan; Kaergona; Kanone; Kappaxan; Kappaxin; Karcon; Kareon; Kativ-G; Kayklot; Kaykot; Kayquinone; Kipca; Kipca-Oil Soluble; Klottone; Koaxin; Kolklot; Menadion; Menaphthon; Menaphthone; Menaquinone; Mitenon; Mitenone; MNQ; Panosine; Prokayvit; Synkay; Thyloquinone; Vitamin K2(0); Vitamin K3; 2-Methyl-1,4-Naphthalenedione; 2-Methyl-1,4-naphthoquinone; 2-Methylnaphthoquinone; 3-Methyl-1,4-naphthoquinone; Juva-K; Menaphtone; Menaquinone O; USAF EK-5185; 2-Methyl-1,4-naphthochinon; 2-Methyl-1,4-naftochinon; 2-Methyl-1,4-naphthalendione; NSC 4170; Menaphthene; Kaynone; Vitamin K0
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Condensed phase thermochemistry data
Go To: Top, 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°solid | -1252. ± 1. | kcal/mol | Ccb | Berliner, 1946 | Corresponding ΔfHºsolid = -56. kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase 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: Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 376. | K | N/A | Grady, Hays, et al., 1973 | Uncertainty assigned by TRC = 1. K |
Gas phase ion energetics data
Go To: Top, 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 as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.765 ± 0.061 | IMRE | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -38.5 kcal/mol; ΔSea(estimated) = -4.0 eu; B |
| 1.752 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -39.0 kcal/mol; ΔSea =-4.0, est. from data in Heinis, Chowdhury, et al., 1988; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.3 | PE | Redchenko, Freimanis, et al., 1980 | LLK |
| 9.46 | PE | Redchenko, Freimanis, et al., 1980 | Vertical value; LLK |
| 9.51 | PE | Dougherty, Younathan, et al., 1978 | Vertical value; LLK |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Berliner, 1946
Berliner, E.,
A relation between the oxidation-reduction potentials of quinones and the resonance energies of quinones and of hydroquinoes,
J. Am. Chem. Soc., 1946, 68, 49-51. [all data]
Grady, Hays, et al., 1973
Grady, L.T.; Hays, S.E.; King, R.H.; Klein, H.R.; Mader, W.J.; Wyatt, D.K.; Zimmere, R.O.,
Drug purity profiles,
J. Pharm. Sci., 1973, 62, 459. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Redchenko, Freimanis, et al., 1980
Redchenko, V.V.; Freimanis, Y.F.; Dregeris, Y.Y.,
Photoelectron Spectroscopy of 2,3-Disubtituted naphthoquinones,
J. Gen. Chem. USSR, 1980, 50, 1507, In original 1847. [all data]
Dougherty, Younathan, et al., 1978
Dougherty, D.; Younathan, E.S.; Voll, R.; Abdulnur, S.; McGlynn, S.P.,
Photoelectron spectroscopy of some biological molecules,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 379. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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