2-Butyne

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.


Gas phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas145.1 ± 1.0kJ/molCmProsen, Maron, et al., 1951ALS
Δfgas148.0 ± 1.5kJ/molCcbWagman, Kilpatrick, et al., 1945Unpublished work of E. J. Prosen; ALS
Quantity Value Units Method Reference Comment
Δcgas-2576.7 ± 0.96kJ/molCmProsen, Maron, et al., 1951Corresponding Δfgas = 145.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
39.1850.Thermodynamics Research Center, 1997p=1 bar. Selected values are in close agreement with other statistically calculated values [ Wagman D.D., 1945].; GT
48.43100.
56.69150.
63.57200.
74.10273.15
78.02298.15
78.32300.
94.73400.
110.38500.
124.30600.
136.49700.
147.14800.
156.45900.
164.551000.
171.591100.
177.711200.
183.01300.
187.61400.
191.71500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
84.56336.07Kistiakowsky G.B., 1940GT
89.66369.46

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C4H5- + Hydrogen cation = 2-Butyne

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr1628. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe; B
Δr1628. ± 14.kJ/molG+TSN/Agas phase; Measured vs pyridine; B
Quantity Value Units Method Reference Comment
Δr1597. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe; B
Δr1596. ± 13.kJ/molIMREN/Agas phase; Measured vs pyridine; B

2Hydrogen + 2-Butyne = Butane

By formula: 2H2 + C4H6 = C4H10

Quantity Value Units Method Reference Comment
Δr-272.4 ± 1.3kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -274.4 ± 0.54 kJ/mol; At 355 K; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, References, Notes

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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C4H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.58 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)775.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity745.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.59 ± 0.02PEBieri, Burger, et al., 1977LLK
9.562 ± 0.005PECarlier, Dubois, et al., 1975LLK
9.61PEEnsslin, Bock, et al., 1974LLK
9.59PEBrogli, Heilbronner, et al., 1973LLK
9.56EILossing, 1972LLK
9.79PEBieri and Asbrink, 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+17.6 ± 0.5?EICoats and Anderson, 1957RDSH
C2H3+14.7 ± 0.2?EICoats and Anderson, 1957RDSH
C3H3+11.04CH3EILossing, 1972LLK
C4H2+16.7 ± 0.3?EICoats and Anderson, 1957RDSH
C4H3+15.1 ± 0.2H2+HEICoats and Anderson, 1957RDSH
C4H4+14.0 ± 0.1H2EICoats and Anderson, 1957RDSH
C4H5+12.1 ± 0.1HEICoats and Anderson, 1957RDSH

De-protonation reactions

C4H5- + Hydrogen cation = 2-Butyne

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr1628. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe; B
Δr1628. ± 14.kJ/molG+TSN/Agas phase; Measured vs pyridine; B
Quantity Value Units Method Reference Comment
Δr1597. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe; B
Δr1596. ± 13.kJ/molIMREN/Agas phase; Measured vs pyridine; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, 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

Gas Phase Spectrum

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

IR spectrum
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

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, 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.

Mass spectrum
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

View image of digitized spectrum (can be printed in landscape orientation).

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-IW- 744
NIST MS number 227606

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Vibrational and/or electronic energy levels

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Takehiko Shimanouchi

Symmetry:   D'3h     Symmetry Number σ = 6


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

a'1 1 CH3 s-str 2916  C  ia 2916 S p liq. Free rotation
a'1 2 C≡C str 2240  E  ia 2310 S p liq. Free rotation, FR(2ν8)
a'1 2 C≡C str 2240  E  ia 2233 S p liq. Free rotation, FR(2ν8)
a'1 3 CH3 s-deform 1380  C  ia 1380 S liq. Free rotation
a'1 4 C-C str 725  E  ia 774 M p liq. Free rotation, FR(2ν16)
a'1 4 C-C str 725  E  ia 693 M p liq. Free rotation, FR(2ν16)
a"1 5 CH3 torsion  ia  ia Free rotation
a"2 6 CH3 s-str 2938  B 2938 S gas  ia Free rotation
a"2 7 CH3 s-deform 1382  B 1382 M gas  ia Free rotation
a"2 8 C-C str 1152  B 1152 W gas  ia Free rotation
e' 9 CH3 d-str 2973  B 2973 S gas Free rotation
e' 10 CH3 d-deform 1456  B 1456 S gas Free rotation
e' 11 CH3 rock 1054  B 1054 M gas Free rotation
e' 12 CCC deform 213  C 213 VW liq. Free rotation
e 13 CH3 d-str 2966  D  ia 2966 W liq. Free rotation
e 14 CH3 d-deform 1448  C  ia 1448 M dp liq. Free rotation
e 15 CH3 rock 1029  C  ia 1029 M dp liq. Free rotation
e 16 CCC deform 371  C  ia 371 S dp liq. Free rotation

Source: Shimanouchi, 1972

Notes

SStrong
MMedium
WWeak
VWVery weak
iaInactive
pPolarized
dpDepolarized
FRFermi resonance with an overtone or a combination tone indicated in the parentheses.
B1~3 cm-1 uncertainty
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty
E15~30 cm-1 uncertainty

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, 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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedSqualane27.463.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.463.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.463.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.462.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane26.473.Zulaïca and Guiochon, 1966Column length: 10. m

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH-100488.Haagen-Smit Laboratory, 1997He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH478.White, Hackett, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB485.Bramston-Cook, 201360. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryOV-101466.Zenkevich, 200525. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryCP-Sil5 CB MS482.Tirillini, Verdelli, et al., 200050. m/0.32 mm/0.4 μm; Program: 0C (3min) => 3C/min => 50C => 5C/min => 220C (30min)

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D., Heats of combustion, formation, and insomerization of ten C4 hydrocarbons, J. Res. NBS, 1951, 46, 106-112. [all data]

Wagman, Kilpatrick, et al., 1945
Wagman, D.D.; Kilpatrick, J.E.; Pitzer, K.S.; Rossini, F.D., Heats, equilibrium constants, and free energies of formation of the acetylene hydrocarbons through the pentynes, to 1,500° K, J. Res. NBS, 1945, 35, 467-496. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Wagman D.D., 1945
Wagman D.D., Heats, equilibrium constants, and free energies of formation of the acetylene hydrocarbons through the pentynes to 1500 K, J. Res. Nat. Bur. Stand., 1945, 35, 467-496. [all data]

Kistiakowsky G.B., 1940
Kistiakowsky G.B., Gaseous heat capacities. III, J. Chem. Phys., 1940, 8, 618-622. [all data]

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

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]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Carlier, Dubois, et al., 1975
Carlier, P.; Dubois, J.E.; Masclet, P.; Mouvier, G., Spectres de photoelectrons des alcynes, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 55. [all data]

Ensslin, Bock, et al., 1974
Ensslin, W.; Bock, H.; Becker, G., Photoelectron spectra and molecular properties. XXX. π interactions in H3Si- H3C-substituted acetylenes, J. Am. Chem. Soc., 1974, 96, 2757. [all data]

Brogli, Heilbronner, et al., 1973
Brogli, F.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E., 230. Die photoelektronen-spektren methyl-substituierter Acetylene, Helv. Chim. Acta, 1973, 56, 2171. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions, Can. J. Chem., 1972, 50, 3973. [all data]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [all data]

Coats and Anderson, 1957
Coats, F.H.; Anderson, R.C., Thermodynamic data from electron-impact measurements on acetylene and substituted acetylenes, J. Am. Chem. Soc., 1957, 79, 1340. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Zulaïca and Guiochon, 1966
Zulaïca, J.; Guiochon, G., Analyse des hauts polymères par chromatographie en phase gazeuse de leurs produits de pyrolyse. II. Application à quelques hydrocarbures macromoléculaires purs, Bull. Soc. Chim. Fr., 1966, 4, 1351-1363. [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Tirillini, Verdelli, et al., 2000
Tirillini, B.; Verdelli, G.; Paolocci, F.; Ciccioli, P.; Frattoni, M., The volatile organic compounds from the mycelium of Tuber borchii Vitt., Phytochemistry, 2000, 55, 8, 983-985, https://doi.org/10.1016/S0031-9422(00)00308-3 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, References