The structures and stabilities of H4C2N2 isomers

D. E. Bernholdt; J. D. Irwin; J. P. Lacosse; S. K. Loushin; K. J. Mattson; J. B. Miers; K. D. Park; L. K. Tanaka; C. E. Dykstra

doi:10.1016/0166-1280(87)85015-7

The structures and stabilities of H₄C₂N₂ isomers

D. E. Bernholdt, J. D. Irwin, J. P. Lacosse, S. K. Loushin, K. J. Mattson, J. B. Miers, K. D. Park, L. K. Tanaka, C. E. Dykstra

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8 Scopus citations

Abstract

Ab initio SCF calculations have been carried out to compare the stabilities of aminoacetonitrile, and of eleven isodesmic H₄C₂N₂ species. It was found that aminoacetonitrile is the most stable. Each of the other eleven molecules contains two CN double bonds, and the largest stability differences arise from whether the central bond is a single CC, CN or NN bond. The most stable structures are with a CC single bond. Stability differences also arise from trans versus cis and transoid versus cisoid configuration differences. These appear to be related to conjugation along the nitrogen and carbon skeletons or to intramolecular hydrogen bonding. The species are potentially important prebiotic species and interstellar molecules, and rotational constants have been calculated to help facilitate spectroscopic identification.

Original language	English
Pages (from-to)	175-183
Number of pages	9
Journal	Journal of Molecular Structure: THEOCHEM
Volume	153
Issue number	1-2
DOIs	https://doi.org/10.1016/0166-1280(87)85015-7
State	Published - Sep 1987
Externally published	Yes

Funding

The donors of the Petroleum .Research Fund, administered by the American Chemical Society, are gratefully acknowledged for support of this work through a grant to C.E.D.

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10.1016/0166-1280(87)85015-7

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title = "The structures and stabilities of H4C2N2 isomers",

abstract = "Ab initio SCF calculations have been carried out to compare the stabilities of aminoacetonitrile, and of eleven isodesmic H4C2N2 species. It was found that aminoacetonitrile is the most stable. Each of the other eleven molecules contains two CN double bonds, and the largest stability differences arise from whether the central bond is a single CC, CN or NN bond. The most stable structures are with a CC single bond. Stability differences also arise from trans versus cis and transoid versus cisoid configuration differences. These appear to be related to conjugation along the nitrogen and carbon skeletons or to intramolecular hydrogen bonding. The species are potentially important prebiotic species and interstellar molecules, and rotational constants have been calculated to help facilitate spectroscopic identification.",

author = "Bernholdt, {D. E.} and Irwin, {J. D.} and Lacosse, {J. P.} and Loushin, {S. K.} and Mattson, {K. J.} and Miers, {J. B.} and Park, {K. D.} and Tanaka, {L. K.} and Dykstra, {C. E.}",

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T1 - The structures and stabilities of H4C2N2 isomers

AU - Bernholdt, D. E.

AU - Irwin, J. D.

AU - Lacosse, J. P.

AU - Loushin, S. K.

AU - Mattson, K. J.

AU - Miers, J. B.

AU - Park, K. D.

AU - Tanaka, L. K.

AU - Dykstra, C. E.

PY - 1987/9

Y1 - 1987/9

N2 - Ab initio SCF calculations have been carried out to compare the stabilities of aminoacetonitrile, and of eleven isodesmic H4C2N2 species. It was found that aminoacetonitrile is the most stable. Each of the other eleven molecules contains two CN double bonds, and the largest stability differences arise from whether the central bond is a single CC, CN or NN bond. The most stable structures are with a CC single bond. Stability differences also arise from trans versus cis and transoid versus cisoid configuration differences. These appear to be related to conjugation along the nitrogen and carbon skeletons or to intramolecular hydrogen bonding. The species are potentially important prebiotic species and interstellar molecules, and rotational constants have been calculated to help facilitate spectroscopic identification.

AB - Ab initio SCF calculations have been carried out to compare the stabilities of aminoacetonitrile, and of eleven isodesmic H4C2N2 species. It was found that aminoacetonitrile is the most stable. Each of the other eleven molecules contains two CN double bonds, and the largest stability differences arise from whether the central bond is a single CC, CN or NN bond. The most stable structures are with a CC single bond. Stability differences also arise from trans versus cis and transoid versus cisoid configuration differences. These appear to be related to conjugation along the nitrogen and carbon skeletons or to intramolecular hydrogen bonding. The species are potentially important prebiotic species and interstellar molecules, and rotational constants have been calculated to help facilitate spectroscopic identification.

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The structures and stabilities of H₄C₂N₂ isomers

Abstract

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