1-Propanol, 2,2-dimethyl-
- Formula: C5H12O
- Molecular weight: 88.1482
- IUPAC Standard InChIKey: KPSSIOMAKSHJJG-UHFFFAOYSA-N
- 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
- 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.
Phase change data
Go To: Top, Reaction thermochemistry 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 385. ± 3. | K | AVG | N/A | Average of 26 out of 27 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 327. | K | N/A | Rai, Singh, et al., 1987 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 325.7 | K | N/A | Murrill and Breed, 1970 | Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 324.45 | K | N/A | McKenna, Tartar, et al., 1953 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 323.15 | K | N/A | Whitmore, 1938 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.4 ± 0.07 | kcal/mol | GS,B | Kulikov, Verevkin, et al., 2001 | Based on data from 274. to 312. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.4 | 345. | A | Stephenson and Malanowski, 1987 | Based on data from 330. to 387. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
0.69 | 328.2 | AC | Straka, van Genderen, et al., 2007 | Based on data from 10. to 370. K.; AC |
0.925 | 329.8 | N/A | Censký, Ruzicka, et al., 2003 | AC |
0.891 | 329.8 | N/A | Salud, López, et al., 1999 | AC |
0.84 | 328.1 | DSC | Granzow, 1996 | AC |
0.970 | 325. | N/A | Murrill and Breed, 1970, 2 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.210 | 146. | Parks, Huffman, et al., 1933 | CAL |
0.19 | 213. | ||
4.034 | 264. |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.067 | 242. | crystaline, II | crystaline, I | Murrill and Breed, 1970, 2 | DH |
0.9696 | 325. | crystaline, I | liquid | Murrill and Breed, 1970, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
4.40 | 242. | crystaline, II | crystaline, I | Murrill and Breed, 1970, 2 | DH |
2.99 | 325. | crystaline, I | liquid | Murrill and Breed, 1970, 2 | DH |
Reaction thermochemistry data
Go To: Top, Phase change 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C5H11O- + =
By formula: C5H11O- + H+ = C5H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372.6 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 373.1 ± 2.3 | kcal/mol | D-EA | Janousek, Zimmerman, et al., 1978 | gas phase; B |
ΔrH° | 372.7 ± 2.0 | kcal/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.0 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 366.5 ± 2.4 | kcal/mol | H-TS | Janousek, Zimmerman, et al., 1978 | gas phase; B |
ΔrG° | 366.1 ± 2.1 | kcal/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
By formula: C8H5- + C5H12O = (C8H5- • C5H12O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24.2 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 15.5 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28.5 | kcal/mol | ICR | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.3 | cal/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 19.8 | kcal/mol | ICR | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
By formula: C5H11O- + C5H12O = (C5H11O- • C5H12O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 29.0 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 19.9 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B |
By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28.4 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 19.7 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Phase change data, Reaction thermochemistry data, 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]
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]
Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E.,
Anion-alcohol hydrogen bond strengths in the gas phase,
J. Am. Chem. Soc., 1984, 106, 4660. [all data]
Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P.,
Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase,
J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076
. [all data]
Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W.,
Relative acidities of water and methanol, and the stabilities of the dimer adducts,
J. Phys. Chem., 1986, 90, 6687. [all data]
Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M.,
Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol,
J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014
. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point 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 ΔrS° Entropy 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
- 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.