1-Propanol, 2,2-dimethyl-

• Formula: C₅H₁₂O
• Molecular weight: 88.1482
• IUPAC Standard InChI: InChI=1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3 Copy

  
• IUPAC Standard InChIKey: KPSSIOMAKSHJJG-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-84-3
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: tert-Butylcarbinol; Neoamyl alcohol; Neopentanol; Neopentyl alcohol; 2,2-Dimethyl-1-propanol; (CH3)3CCH2OH; 2,2-Dimethylpropyl alcohol; tert-Amyl alcohol; 2,2-Dimethylpropanol; 2-Methyl-isobutanol; 2,2,2-Trimethylethanol
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• Information on this page:
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₅H₁₂O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₅H₁₁O^- +  =

By formula: C₅H₁₁O^- + H⁺ = C₅H₁₂O

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

References

Go To: Top, Phase change data, Henry's Law 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.

Rai, Singh, et al., 1987
Rai, U.S.; Singh, O.P.; Singh, N.B., Solidification behavior of organic eutectic, succinonitrile-neopenty alcohol system, J. Chim. Phys. Phys.-Chim. Biol., 1987, 84, 483. [all data]

Murrill and Breed, 1970
Murrill, E.; Breed, L.W., Solid-solid phase transitions determined by differential scanning calorime- try. Part I. Tetrahedral Substances., Thermochim. Acta, 1970, 1, 239. [all data]

McKenna, Tartar, et al., 1953
McKenna, F.E.; Tartar, H.V.; Lingafelter, E.C., Studies of hemiacetal formation in alcohol - aldehyde systems: II refraction studies, J. Am. Chem. Soc., 1953, 75, 604-7. [all data]

Whitmore, 1938
Whitmore, F.C., The Reducing Action of Grignard Reagents on Acyl Chlorides, Recl. Trav. Chim. Pays-Bas, 1938, 57, 562. [all data]

Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas, Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C ₅ and C ₆ Alcohols, J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p . [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]

Straka, van Genderen, et al., 2007
Straka, Martin; van Genderen, Aad; Ruzicka, Kvetoslav; Ruzicka, Vlastimil, Heat Capacities in the Solid and in the Liquid Phase of Isomeric Pentanols, J. Chem. Eng. Data, 2007, 52, 3, 794-802, https://doi.org/10.1021/je060411g . [all data]

Censký, Ruzicka, et al., 2003
Censký, Miroslav; Ruzicka, Kvetoslav; Ruzicka, Vlastimil; Zábranský, Milan, Heat capacities of alkanols, Thermochimica Acta, 2003, 408, 1-2, 45-53, https://doi.org/10.1016/S0040-6031(03)00317-4 . [all data]

Salud, López, et al., 1999
Salud, Josep; López, David O.; Barrio, Maria; Tamarit, Josep Ll., Two-component systems of isomorphous orientationally disordered crystals. Part 1 Packing of the mixed crystals, J. Mater. Chem., 1999, 9, 4, 909-916, https://doi.org/10.1039/a808258h . [all data]

Granzow, 1996
Granzow, Bettina, Hydrogen bonding and phase transitions of a group of alcohols derived from 2,2-dimethylpropane, Journal of Molecular Structure, 1996, 381, 1-3, 127-131, https://doi.org/10.1016/0022-2860(96)09232-0 . [all data]

Murrill and Breed, 1970, 2
Murrill, E.; Breed, L., Solid-solid phase transitions determined by differential scanning calorimetry, Thermochim. Acta, 1970, 1, 239-246. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen, J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Bissonnette, George, et al., 1990
Bissonnette, M.; George, M.; Holmes, J.L., The experimental investigation of [C₅H₁₂O] ion structures related to neopentyl alcohol and its methyl ether, Int. J. Mass Spectrom. Ion Processes, 1990, 101, 309. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Janousek, Zimmerman, et al., 1978
Janousek, B.K.; Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Electron detachment from aliphatic molecular anions. Gas phase electron affinites of methoxyl, tert-butoxyl, and neopentoxyl radicals, J. Am. Chem. Soc., 1978, 100, 6142. [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Anker, Jurs, et al., 1990
Anker, L.S.; Jurs, P.C.; Edwards, P.A., Quantitative structure-retention relationship studies of odor-active aliphatic compounds with oxygen-containing functional groups, Anal. Chem., 1990, 62, 24, 2676-2684, https://doi.org/10.1021/ac00223a006 . [all data]

Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F., Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies, Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction 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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