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Gas-phase diels-alder cycloaddition reaction in the presence of methanol and water vapor

Gholami, M. R ; Sharif University of Technology | 2003

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  1. Type of Document: Article
  2. DOI: 10.1002/poc.577
  3. Publisher: 2003
  4. Abstract:
  5. Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methanol increases the reaction rate in the gas phase more than the water. This is attributed to the stronger hydrogen bonding effect of methanol in this phase. Ab initio and semi-empirical calculations show that methanol stabilizes the transition state of the reaction more than water. This arises from two different origins, distribution of charge and geometry of the hydrogen bond. Copyright © 2002 John Wiley & Sons, Ltd
  6. Keywords:
  7. Cycloaddition reaction ; Gas phase kinetics ; Hydrogen bonding ; Solvent effect ; Theoretical study
  8. Source: Journal of Physical Organic Chemistry ; Volume 16, Issue 1 , 2003 , Pages 79-83 ; 08943230 (ISSN)
  9. URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.577