Niacin
- Formula: C6H5NO2
- Molecular weight: 123.1094
- IUPAC Standard InChI: InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
- IUPAC Standard InChIKey: PVNIIMVLHYAWGP-UHFFFAOYSA-N
- CAS Registry Number: 59-67-6
- 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: 3-Pyridinecarboxylic acid; Nicotinic acid; Akotin; Apelagrin; Daskil; Efacin; Linic; Nicacid; Nicangin; Nico-Span; Nicodelmine; Nicolar; Niconacid; Nicosan 3; Nicotinipca; Nicyl; Nyclin; Pellagrin; Pelonin; Pyridine-β-carboxylic acid; 3-Carboxylpyridine; 3-Carboxypyridine; anti-Pellagra vitamin; Acidum nicotinicum; Bionic; Davitamon PP; Diacin; Direktan; Naotin; Niac; Nicamin; Nico-400; Nicobid; Nicocap; Nicocidin; Nicocrisina; Nicodan; Nicodon; Niconat; Niconazid; Nicorol; Nicoside; Nicosyl; Nicotamin; Nicotene; Nicotil; Nicotine acid; Nicotinsaure; Nicovasan; Nicovasen; Nicovel; Nipellen; NICO; P.P. factor-pellagra preventive factor; Pellagra preventive factor; Pellagramin; Peviton; Pyridine-3-carboxylic acid; PP Factor; SK-Niacin; S115; Tega-Span; Vitaplex N; Wampocap; Acide nicotinique; Kyselina nikotinova; NAH; Pyridine-carboxylique-3; Tinic; m-Pyridinecarboxylic acid; β-Pyridinecarboxylic acid; 3-Pyridylcarboxylic acid; Niacor; P.P. factor; Vitamin B3; Niaspan; Vitamin B5
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Gas phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -221.5 ± 1.5 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values |
Condensed phase thermochemistry data
Go To: Top, Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -344.9 ± 0.9 | kJ/mol | Ccb | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values |
| ΔfH°solid | -344.81 ± 0.92 | kJ/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values |
| ΔfH°solid | -344.97 ± 0.67 | kJ/mol | Ccr | Johnson, 1975 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2730.83 ± 0.48 | kJ/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values |
| ΔcH°solid | -2730.67 ± 0.57 | kJ/mol | Ccr | Johnson, 1975 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.38 | PE | Dougherty, Younathan, et al., 1978 | LLK |
De-protonation reactions
C6H4NO2- + =
By formula: C6H4NO2- + H+ = C6H5NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1399. ± 8.4 | kJ/mol | CIDC | Schafman and Wenthold, 2007 | gas phase; B |
| ΔrH° | 1395. ± 12. | kJ/mol | G+TS | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1370. ± 9.2 | kJ/mol | H-TS | Schafman and Wenthold, 2007 | gas phase; B |
| ΔrG° | 1366. ± 11. | kJ/mol | IMRB | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Bickerton, Pilcher, et al., 1984
Bickerton, J.; Pilcher, G.; Al-Takhin, G.,
Enthalpies of combustion of the three aminopyridines and the three cyanopyridines,
J. Chem. Thermodyn., 1984, 16, 373-378. [all data]
Sato-Toshima, Kamagughi, et al., 1983
Sato-Toshima, T.; Kamagughi, A.; Nishiyama, K.; Sakiyama, M.; Seki, S.,
Enthalpies of combustion of organic compounds. IV. Acetaneilide and nicotinic acid,
Bull. Chem. Soc. Jpn., 1983, 56, 51-54. [all data]
Johnson, 1975
Johnson, W.H.,
The enthalpies of combustion and formation of nicotinic acid and creatinine,
J. Res. NBS, 1975, 79, 425-429. [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]
Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G.,
Regioselectivity of pyridine deprotonation in the gas phase,
J. Org. Chem., 2007, 72, 5, 1645-1651, https://doi.org/10.1021/jo062117x
. [all data]
Breuker, Knochenmuss, et al., 1999
Breuker, K.; Knochenmuss, R.; Zenobi, R.,
Gas-phase basicities of deprotonated matrix-assisted laser desorption/ionization matrix molecules,
Int. J. Mass Spectrom., 1999, 184, 1, 25-38, https://doi.org/10.1016/S1387-3806(98)14200-8
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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