Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions

作者：Domingo, Luis R.^*; Perez, Patricia; Saez, Jose A.

来源：RSC Advances, 2013, 3(5): 1486-1494.

DOI：10.1039/c2ra22886f

• DIELS-ALDER REACTION
• BOND-FORMATION
• ELF ANALYSIS
• LOCALIZATION FUNCTION
• REGIOSELECTIVITY
• 1,3-DIPOLAR
• ORIGIN
• DFT

Building upon our recent studies devoted to the bonding changes in polar reactions [RSC Advances, 2012, 2, 1334 and Org. Biomol. Chem., 2012, 10, 3841], we propose herein two new electrophilic, P-k(+), and nucleophilic, P-k(-), Parr functions based on the spin density distribution at the radical anion and at the radical cation of a neutral molecule. These local functions allow for the characterisation of the most electrophilic and nucleophilic centres of molecules, and for the establishment of the regio- and chemoselectivity in polar reactions. The proposed Parr functions are compared with both, the Parr-Yang Fukui functions [J. Am. Chem. Soc. 1984, 106, 4049] based on frontier molecular orbitals, and Yang-Mortier condensed Fukui functions [J. Am. Chem. Soc. 1986, 108, 5708] based on Mulliken charges.

• 出版日期2013