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2-Butynedinitrile

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Gas 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas533.46kJ/molReviewChase, 1998Data last reviewed in March, 1961
Deltafgas529.3kJ/molCcbArmstrong and Marantz, 1963Correction of Armstrong and Marantz, 1960; ALS
Quantity Value Units Method Reference Comment
gas,1 bar290.11J/mol*KReviewChase, 1998Data last reviewed in March, 1961

Gas Phase Heat Capacity (Shomate Equation)

Cp° = A + B*t + C*t2 + D*t3 + E/t2
H° − H°298.15= A*t + B*t2/2 + C*t3/3 + D*t4/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t2/2 + D*t3/3 − E/(2*t2) + G
    Cp = heat capacity (J/mol*K)
    H° = standard enthalpy (kJ/mol)
    S° = standard entropy (J/mol*K)
    t = temperature (K) / 1000.

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Temperature (K) 298. - 1200.1200. - 6000.
A 75.60488129.7793
B 70.610863.927480
C -29.19311-0.764036
D 3.4523360.051342
E -0.734589-14.12284
F 505.5695462.7922
G 357.6889404.6660
H 533.4600533.4600
ReferenceChase, 1998Chase, 1998
Comment Data last reviewed in March, 1961 Data last reviewed in March, 1961

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

Quantity Value Units Method Reference Comment
Deltafliquid500.4kJ/molCcbArmstrong and Marantz, 1963Correction of Armstrong and Marantz, 1960
Quantity Value Units Method Reference Comment
Deltacliquid-2074.4 ± 1.3kJ/molCcbArmstrong and Marantz, 1963Reanalyzed by Cox and Pilcher, 1970, Original value = -2073. ± 0.8 kJ/mol; Correction of Armstrong and Marantz, 1960
Quantity Value Units Method Reference Comment
Deltacsolid-2156.kJ/molCcbMoureu and Bongrand, 1920 

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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil349.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Deltavap28.9kJ/molN/AArmstrong and Marantz, 1963DRB
Quantity Value Units Method Reference Comment
Deltasub44.246kJ/molVSaggiomo, 1957Hfusion=3.700 kcal/mol; ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
27.3310.AStephenson and Malanowski, 1987Based on data from 295. - 350. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
44.3268.ISAGGIOMO, 1957Based on data from 263. - 273. K. See also Govers, 1975 and Stephenson and Malanowski, 1987.; AC

Reaction 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

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

2-Butynedinitrile + 1,3 Diphenylisobenzofuran = C24H16N2O

By formula: C4N2 + C20H14O = C24H16N2O

Quantity Value Units Method Reference Comment
Deltar-129.kJ/molKinSamuilov, Nurullina, et al., 1983liquid phase; solvent: Nonaquous

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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference Comment
11.81 ± 0.02PIPECOMaier, Misev, et al., 1982LBLHLM
11.81 ± 0.01PIBaker and Turner, 1968RDSH
11.4 ± 0.2EIDibeler, Reese, et al., 1961RDSH
11.84PEAsbrink, Von Niessen, et al., 1980Vertical value; LLK
11.84PEBieri, Heilbronner, et al., 1979Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C+24. ± 1.0?EIDibeler, Reese, et al., 1961RDSH
CN+19.2 ± 0.3?EIDibeler, Reese, et al., 1961RDSH
C2+18.5 ± 0.3?EIDibeler, Reese, et al., 1961RDSH
C2N+18.1 ± 0.4?EIDibeler, Reese, et al., 1961RDSH
C3+24.6?EIDibeler, Reese, et al., 1961RDSH
C3N+18.4 ± 0.2CNEIDibeler, Reese, et al., 1961RDSH
C4+17.2 ± 0.2N2EIDibeler, Reese, et al., 1961RDSH
C4N+18.8 ± 0.5NEIDibeler, Reese, et al., 1961RDSH
N+26.0 ± 1.0?EIDibeler, Reese, et al., 1961RDSH

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

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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.
NIST MS number 367

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, Notes

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

Chase, 1998
Chase, M.W., Jr., NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951. [all data]

Armstrong and Marantz, 1963
Armstrong, G.T.; Marantz, S., The heat of combustion of dicyanoacetylene [Correction Ref. 60ARM/MAR], J. Phys. Chem., 1963, 67, 2888. [all data]

Armstrong and Marantz, 1960
Armstrong, G.T.; Marantz, S., The heat of combustion of dicyanoacetylene, J. Phys. Chem., 1960, 64, 1776-1778. [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]

Moureu and Bongrand, 1920
Moureu, M.C.; Bongrand, J.Ch., Thermochimie. - Nouvelles recherches sur le sous-azolure de carbone. Action des halogenes, des acides halohydriques et des alcools, Compt. Rend., 1920, 170, 1025-1028. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Saggiomo, 1957
Saggiomo, A.J., The dinitriles of acetylenedicarboxylic and polyacetylenedicarboxylic acids. I. Dicyanoacetylene and dicycanodiacetylene, J. Org. Chem., 1957, 22, 1171. [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]

SAGGIOMO, 1957
SAGGIOMO, ANDREW J., The Dinitriles of Acetylenedicarboxylic and Polyacetylenedicarboxylic Acids. 1 I. 2 Dicyanoacetylene and Dicyanodiacetylene, J. Org. Chem., 1957, 22, 10, 1171-1175, https://doi.org/10.1021/jo01361a009 . [all data]

Govers, 1975
Govers, H.A.J., Derivation of carbon--nitrogen, hydrogen--nitrogen and nitrogen--nitrogen non-bonded potential parameters in molecular crystals, Acta Crystallogr Sect A Cryst Phys Diffr Theor Gen Crystallogr', 1975, 31, 3, 380-385, https://doi.org/10.1107/S0567739475000800 . [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Maier, Misev, et al., 1982
Maier, J.P.; Misev, L.; Thommen, F., Dicyanoacetylene cation. Laser-induced fluorescence and photoelectron-photon coincidence studies, J. Phys. Chem., 1982, 86, 514. [all data]

Baker and Turner, 1968
Baker, C.; Turner, D.W., High resolution molecular photoelectron spectroscopy. III.Acetylenes and azaacetylenes, Proc. Roy. Soc. (London), 1968, A308, 19. [all data]

Dibeler, Reese, et al., 1961
Dibeler, V.H.; Reese, R.M.; Franklin, J.L., Mass spectrometric study of cyanogen and cyanoacetylenes, J. Am. Chem. Soc., 1961, 83, 1813. [all data]

Asbrink, Von Niessen, et al., 1980
Asbrink, L.; Von Niessen, W.; Bieri, G., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 21, 93. [all data]

Bieri, Heilbronner, et al., 1979
Bieri, G.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E.; Maier, J.P.; Thommen, F.; von Niessen, W., Electronic states of substituted haloacetylene and cyanoacetylene radical cations, Chem. Phys., 1979, 36, 1. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, References