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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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: John E. Bartmess
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
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 |
| ΔrH° | 1395. ± 12. | kJ/mol | G+TS | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1370. ± 9.2 | kJ/mol | H-TS | Schafman and Wenthold, 2007 | gas phase |
| ΔrG° | 1366. ± 11. | kJ/mol | IMRB | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (1 mg / 200 mg KBr DISC) VS KBr; PERKIN-ELMER 21 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLID (NUJOL MULL); PERKIN-ELMER 21 (GRATING) $$SPECTRAL CONTAMINATION DUE TO OIL AROUND 2880 CM-1; 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | Japan AIST/NIMC Database- Spectrum MS-NW-5913 |
| NIST MS number | 233225 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
| Source | Bartecki, Szoke, et al., 1966 |
|---|---|
| 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. 8651 |
| Instrument | Beckman DU |
| Melting point | 236.6 |
| Boiling point | sub |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
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]
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]
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]
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]
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]
Bartecki, Szoke, et al., 1966
Bartecki, A.; Szoke, J.; Varsanyi, G.; Vizesy, M.,
Absorption spectra in the ultraviolet and visible region. Volume 3, Academic Press Inc., New York, 1966, 278. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition 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 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.