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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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 510.48 | K | N/A | Malaviolle, De Maury, et al., 1987 | Uncertainty assigned by TRC = 0.5 K; determined for various conditions and heating rates; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 123.9 ± 3.7 | kJ/mol | ME | Ribeiro da Silva, Gonçalves, et al., 2000 | Based on data from 352. to 360. K.; AC |
| ΔsubH° | 105.2 ± 0.6 | kJ/mol | N/A | Sabbah and Ider, 1999 | AC |
| ΔsubH° | 123.4 ± 1.2 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values; ALS |
| ΔsubH° | 123.4 ± 1.2 | kJ/mol | C | Bickerton, Pilcher, et al., 1984 | AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 89.3 | 473. to 498. | TG,DTA | Menon, Dollimore, et al., 2002 | AC |
| 101.1 ± 0.6 | 362. | C | Sabbah and Ider, 1999 | AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 30.000 | 510. | Allan, Geddes, et al., 1989 | DH |
| 27.57 | 509.1 | Wang, Tan, et al., 2004 | AC |
| 97.1 | 509.3 | Wang and Wang, 2004 | This value is considerably larger than values below—likely in error.; AC |
| 26.7 | 510. | El Moussaoui, Chauvet, et al., 1993 | AC |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 0.780 | 451.95 | crystaline, II | crystaline, I | El Moussaoui, Chauvet, et al., 1993, 2 | DH |
| 26.700 | 509.75 | crystaline, I | liquid | El Moussaoui, Chauvet, et al., 1993, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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 |
Gas Chromatography
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-1 | 130. | 1340. | Japp, Gill, et al., 1987 | 30. m/0.53 mm/1.5 μm, N2 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1335. | Perrigo and Peel, 1981 | N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Other | Methyl Silicone | 1335. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Malaviolle, De Maury, et al., 1987
Malaviolle, R.; De Maury, G.; Chauvet, A.; Terol, A.; Masse, J.,
Study of the Binaries Khelline I - Nicotinic Acid and Khelline I - Nicotinamide,
Thermochim. Acta, 1987, 121, 283. [all data]
Ribeiro da Silva, Gonçalves, et al., 2000
Ribeiro da Silva, Maria D.M.C.; Gonçalves, Jorge M.; Acree, W.E., Jr.,
Standard molar enthalpy of sublimation of crystalline 3-pyridinecarboxylic acid,
The Journal of Chemical Thermodynamics, 2000, 32, 8, 1071-1073, https://doi.org/10.1006/jcht.2000.0675
. [all data]
Sabbah and Ider, 1999
Sabbah, Raphaël; Ider, Safi,
Energétique des liaisons inter- et intramoléculaires dans les trois acides carboxypyridiniques (acides picolinique, nicotinique et isonicotinique),
Revue canadienne de chimie, 1999, 77, 2, 249-257, https://doi.org/10.1139/cjc-77-2-249
. [all data]
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]
Menon, Dollimore, et al., 2002
Menon, Divya; Dollimore, David; Alexander, Kenneth S.,
A TG--DTA study of the sublimation of nicotinic acid,
Thermochimica Acta, 2002, 392-393, 237-241, https://doi.org/10.1016/S0040-6031(02)00106-5
. [all data]
Allan, Geddes, et al., 1989
Allan, J.R.; Geddes, W.C.; Hindle, C.S.; Orr, A.E.,
Thermal analysis studies on pyridine carboxylic acid complexes of zinc(II),
Thermochim. Acta, 1989, 153, 249-256. [all data]
Wang, Tan, et al., 2004
Wang, S.X.; Tan, Z.C.; Di, Y.Y.; Xu, F.; Wang, M.H.; Sun, L.X.; Zhang, T.,
Calorimetric study and thermal analysis of crystalline nicotinic acid,
Journal of Thermal Analysis and Calorimetry, 2004, 76, 1, 335-342, https://doi.org/10.1023/B:JTAN.0000027833.24442.a0
. [all data]
Wang and Wang, 2004
Wang, Liu-Cheng; Wang, Fu-An,
Solubilities of niacin in sulfuric acid + water and 3-picoline + sulfuric acid + water from (292.65--361.35) K,
Fluid Phase Equilibria, 2004, 226, 289-293, https://doi.org/10.1016/j.fluid.2004.06.050
. [all data]
El Moussaoui, Chauvet, et al., 1993
El Moussaoui, A.; Chauvet, A.; Masse, J.,
Solid-state interaction of nordazepam-III and nicotinic-acid,
J. Therm. Anal., 1993, 39, 5, 619. [all data]
El Moussaoui, Chauvet, et al., 1993, 2
El Moussaoui, A.; Chauvet, A.; Masse, J.,
Study of the solid-state interactions of Nordazepam III-nicotinic acid binary,
J. Therm. Anal., 1993, 39(5), 619-632. [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]
Japp, Gill, et al., 1987
Japp, M.; Gill, R.; Osselton, M.D.,
Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns,
J. Forensic Sci., 1987, 32, 6, 1574-1586. [all data]
Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W.,
The use of retention indices and temperature-programmed gas chromatography in analytical toxicology,
J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219
. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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