Ab initio study of solvent effects on rate of 1,3-dipolar cycloadditions of benzonitrile oxide and various dipolarophiles

Rajaeian, E ; Sharif University of Technology | 2003

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  1. Type of Document: Article
  2. Publisher: 2003
  3. Abstract:
  4. Ab initio molecular orbital calculations have been used to investigate the structures and the transition states of 1,3-dipolar cycloadditions between benzonitrile oxide with ethylene, cyclopentene, acrylonitrile and tetracyanoethylene in heptane and water: calculations reveal enhanced hydrogen bonding of a water molecule to the transition states for the cycloaddition 1,3-dipolar of reaction of benzonitrile oxide with cyclopentene, the optimal interaction energies being 0.7 kcal/mol more favourable for hydrogen bonding to the oxygen atom in the transition states than for the reactants
  5. Keywords:
  6. 1,3-dipolar cycloaddition ; Ab initio ; Hydrogen bonding ; Hydrophobic interactions ; Reaction field
  7. Source: Journal of Chemical Research - Part S ; Issue 2 , 2003 , Pages 91-95 ; 03082342 (ISSN)
  8. URL: https://journals.sagepub.com/doi/abs/10.3184/030823403103173075