The Thermodynamic Conjugation Stabilization of 1,3-Butadiyne Is Zero

• Donald W. Rogers ^[1] ; Andreas A. Zavitsas ^[1] ; Nikita Matsunaga ^[1]
  1. [1] Long Island University

     Long Island University

     Town of Oyster Bay, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 12 (December), 2010, págs. 1357-1359
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • Many textbooks point out that the thermodynamic stabilization enthalpy of 1 mol of 1,3-butadiene relative to 2 mol of 1-butene or to 1 mol of 1,4-pentadiene is slightly less than 4 kcal mol−1, owing to conjugation between the double bonds in the 1,3 configuration. It is reasonable to suppose that the analogous thermochemical stabilization enthalpy of 1,3-butadiyne would be somewhat greater than 4 kcal mol−1, perhaps as high as 7 or 8 kcal mol−1. Thus it was with some surprise that we discovered, as subsequently verified by other groups, that the thermodynamic stabilization enthalpy of 1,3-butadiyne is zero.