The Conjugation Stabilization of 1,3-Butadiyne Is Zero

The Conjugation Stabilization of 1,3-Butadiyne Is Zero

In contrast to 1,3-butadiene, the textbook example of “conjugation stabilization”, G3(MP2) calculations yielding the enthalpy of hydrogenation Δhyd H 298 of 1,3-butadiyne indicate that it is not stabilized by the conjugated configuration of its triple bonds. Differences between ethylenic and acetyle...

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Veröffentlicht in:Organic letters 2003-07, Vol.5 (14), p.2373-2375
Hauptverfasser: Rogers, Donald W, Matsunaga, Nikita, Zavitsas, Andreas A, McLafferty, Frank J, Liebman, Joel F
Format: Artikel
Sprache:eng
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Zusammenfassung:In contrast to 1,3-butadiene, the textbook example of “conjugation stabilization”, G3(MP2) calculations yielding the enthalpy of hydrogenation Δhyd H 298 of 1,3-butadiyne indicate that it is not stabilized by the conjugated configuration of its triple bonds. Differences between ethylenic and acetylenic π bonds are examined in the light of CAS-MCSCF calculations on 1,3-butadiene and 1,3-butadiyne.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030019h