α-Pinene

• Formula: C₁₀H₁₆
• Molecular weight: 136.2340
• IUPAC Standard InChI: InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3 Copy

  
• IUPAC Standard InChIKey: GRWFGVWFFZKLTI-UHFFFAOYSA-N Copy
• CAS Registry Number: 80-56-8
• 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.
• Species with the same structure:
  • α-Pinene
• Stereoisomers:
  • (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  • (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Other names: Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-; 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; Pinene, α; 2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene; 2,6,6-Trimethylbicyclo[3.1.1]-2-heptene; Acintene A; 4,6,6-Trimethylbicyklo(3,1,1)hept-3-en; UN 2368; alpha-Pinene; PC 500; Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-; Sylvapine A; (.+/-.)-α-Pinene; NSC 7727; Pinene; (+)-α-pinene; 2,6,6-trimethylbicyclo[3,1,1]-heptene (α-pinene); α-Pinene [1R-(+), 1S-(-) ]; 2,6,6-trimethylbicyclo-[3,1,1]-2-heptene (α-pinene); pin-2(3)-ene
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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

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

References

Go To: Top, Condensed phase thermochemistry data, Phase change 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.

Hawkins and Eriksen, 1954
Hawkins, J.E.; Eriksen, W.T., Physical and thermodynamic properties of terpenes. II. The heats of combustion of some terpene hydrocarbons, J. Am. Chem. Soc., 1954, 76, 2669-26. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Hawkins and Eriksen. W.T., 1954
Hawkins, J.E.; Eriksen. W.T., J. Am. Chem. Soc., 1954, 76, 2669. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]

Clara, Marigliano, et al., 2009
Clara, Rene A.; Marigliano, Ana C. Gomez; Solimo, Horacio N., Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of α-Pinene, d -Limonene, (±)-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure, J. Chem. Eng. Data, 2009, 54, 3, 1087-1090, https://doi.org/10.1021/je8007414 . [all data]

An, Hu, et al., 1987
An, Xuwu; Hu, Riheng; Wang, Hu; Wu, Mali; Zou, Yongkuang, Enthalpies of Vaporization of α- and β-Pinene, Acta Phys. Chim. Sin., 1987, 3, 6, 668-671, https://doi.org/10.3866/PKU.WHXB19870621 . [all data]

Rodrigues and Bernardo-Gil, 1996
Rodrigues, M. Fátima; Bernardo-Gil, M. Gabriela, Vapor-Liquid Equilibrium Data of α-Pinene + β-Pinene + Limonene at 80 kPa and 101 kPa, J. Chem. Eng. Data, 1996, 41, 3, 581-585, https://doi.org/10.1021/je950324g . [all data]

Reich and Sanhueza, 1993
Reich, Ricardo; Sanhueza, Vilma, Vapor-liquid equilibria for .alpha.-pinene or .beta.-pinene with anisole, J. Chem. Eng. Data, 1993, 38, 3, 341-343, https://doi.org/10.1021/je00011a001 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Bukala, Majewski, et al., 1954
Bukala, M.; Majewski, J.; Rodzinski, W., Przem. Chem., 1954, 10, 6. [all data]

Hawkins and Armstrong, 1954
Hawkins, J.E.; Armstrong, G.T., Physical and thermodynamic properties of terpenes. III. The vapor pressures of α-pinene and β-pinene, J. Am. Chem. Soc., 1954, 76, 3756-37. [all data]

Hawkinds and Armstrong, 1954
Hawkinds, J.E.; Armstrong, G.T., Physical and Thermodynamic Properties of Terpenes. III. The Vapor Pressures of α-Pinene and β-Pinene, J. Am. Chem. Soc., 1954, 76, 14, 3756-3759, https://doi.org/10.1021/ja01643a051 . [all data]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [all data]

O'Connor and Goldblatt, 1954
O'Connor, R.T.; Goldblatt, L.A., Correlation of ultraviolet and infrared spectra of terpene hydrocarbons, Anal. Chem., 1954, 26, 11, 1726-1737. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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