Approaching the double-faceted nature of the CX bond in halobenzenes with a bifunctional probe

作者：El Hage Krystel; Piquemal Jean Philip; Hobaika Zeina; Maroun Richard G; Gresh Nohad^*

来源：Chemical Physics Letters, 2015, 637: 51-57.

DOI：10.1016/j.cplett.2015.07.047

In halobenzenes, the CX bond (X = Cl, Br) is doubly faceted, electron-deficient along the CX direction, and electron-rich on its flanks. We have recently shown that both features could be enhanced by appropriate electron-withdrawing and electron-donating groups, respectively. In this letter we further highlight this dual character by approaching a bifunctional probe, N-methylformamide, to both regions in representative substituted halobenzenes. We report the results of interaction energy computations, ELF, and NCI analyses. These methods used in conjunction show the responsiveness of the CX bond to both kinds of substitutions, enabling significant interaction energy gains with respect to the parent compound.

• 出版日期2015-9-16