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) Copy

  
• IUPAC Standard InChIKey: PVNIIMVLHYAWGP-UHFFFAOYSA-N Copy
• 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:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Phase change data

Go To: Top, Gas phase ion energetics data, 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 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

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Gas phase ion energetics data

Go To: Top, Phase change data, 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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₆H₄NO₂^- +  =

By formula: C₆H₄NO₂^- + H⁺ = C₆H₅NO₂

Mass spectrum (electron ionization)

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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
• 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.