Niacin
- Formula: C6H5NO2
- Molecular weight: 123.1094
- 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, 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 | -52.94 ± 0.36 | kcal/mol | Ccb | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values |
Condensed phase thermochemistry data
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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 | -82.4 ± 0.2 | kcal/mol | Ccb | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values |
ΔfH°solid | -82.41 ± 0.22 | kcal/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values |
ΔfH°solid | -82.45 ± 0.16 | kcal/mol | Ccr | Johnson, 1975 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -652.68 ± 0.11 | kcal/mol | Ccr | Sato-Toshima, Kamagughi, et al., 1983 | Author was aware that data differs from previously reported values |
ΔcH°solid | -652.65 ± 0.14 | kcal/mol | Ccr | Johnson, 1975 |
Phase change data
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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° | 29.61 ± 0.88 | kcal/mol | ME | Ribeiro da Silva, Gonçalves, et al., 2000 | Based on data from 352. to 360. K.; AC |
ΔsubH° | 25.1 ± 0.1 | kcal/mol | N/A | Sabbah and Ider, 1999 | AC |
ΔsubH° | 29.49 ± 0.29 | kcal/mol | C | Bickerton, Pilcher, et al., 1984 | Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 29.49 ± 0.29 | kcal/mol | C | Bickerton, Pilcher, et al., 1984 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.3 | 473. to 498. | TG,DTA | Menon, Dollimore, et al., 2002 | AC |
24.2 ± 0.1 | 362. | C | Sabbah and Ider, 1999 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.1702 | 510. | Allan, Geddes, et al., 1989 | DH |
6.589 | 509.1 | Wang, Tan, et al., 2004 | AC |
23.2 | 509.3 | Wang and Wang, 2004 | This value is considerably larger than values below—likely in error.; AC |
6.38 | 510. | El Moussaoui, Chauvet, et al., 1993 | AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.186 | 451.95 | crystaline, II | crystaline, I | El Moussaoui, Chauvet, et al., 1993, 2 | DH |
6.3815 | 509.75 | crystaline, I | liquid | El Moussaoui, Chauvet, et al., 1993, 2 | DH |
Reaction thermochemistry data
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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° | 334.4 ± 2.0 | kcal/mol | CIDC | Schafman and Wenthold, 2007 | gas phase |
ΔrH° | 333.4 ± 2.9 | kcal/mol | G+TS | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 327.4 ± 2.2 | kcal/mol | H-TS | Schafman and Wenthold, 2007 | gas phase |
ΔrG° | 326.4 ± 2.7 | kcal/mol | IMRB | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid |
Gas phase ion energetics data
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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° | 334.4 ± 2.0 | kcal/mol | CIDC | Schafman and Wenthold, 2007 | gas phase; B |
ΔrH° | 333.4 ± 2.9 | kcal/mol | G+TS | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 327.4 ± 2.2 | kcal/mol | H-TS | Schafman and Wenthold, 2007 | gas phase; B |
ΔrG° | 326.4 ± 2.7 | kcal/mol | IMRB | Breuker, Knochenmuss, et al., 1999 | gas phase; Acid: nicotinic acid; B |
IR Spectrum
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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)
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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
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Additional Data
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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
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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
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Additional Data
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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
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