Theoretical investigation of the NO₃radical addition to double bonds of limonene

Int J Mol Sci. 2009 Aug 27;10(9):3743-3754. doi: 10.3390/ijms10093743.

Abstract

The addition reactions of NO(3) to limonene have been investigated using ab initio methods. Six different possibilities for NO(3) addition to the double bonds, which correspond to the two C-C double bonds (endocyclic or exocyclic) have been considered. The negative activation energies for the addition of NO(3) to limonene are calculated and the energies of NO(3)-limonene radical adducts are found to be 14.55 to 20.17 kcal mol-1 more stable than the separated NO(3) and limonene at the CCSD(T)/6-31G(d) + CF level. The results also indicate that the endocyclic addition reaction is more energetically favorable than the exocyclic one.

Keywords: ab initio; limonene; nitrate radical (NO3); volatile organic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Computer Simulation
  • Cyclohexenes / chemistry*
  • Free Radicals / chemistry*
  • Limonene
  • Models, Chemical
  • Nitric Acid / chemistry*
  • Quantum Theory
  • Terpenes / chemistry*
  • Thermodynamics
  • Volatile Organic Compounds / chemistry

Substances

  • Cyclohexenes
  • Free Radicals
  • Terpenes
  • Volatile Organic Compounds
  • Nitric Acid
  • Limonene