TY  - JOUR
  - Jennings, WB,Farrell, BA,Malone, JF
  - 2006
  - March
  - The Journal of Organic Chemistry
  - Stereodynamics and edge-to-face CH-pi aromatic interactions in O-phenethyl-substituted biaryls
  - Validated
  - ()
  - CRYSTAL-STRUCTURE SUPRAMOLECULAR STRUCTURES METAL-COMPLEXES CONFORMATION DERIVATIVES LIGANDS BINDING IMINES
  - 71
  - 2277
  - 2282
  - [GRAPHICS]As part of a search for systems that exhibit intramolecular aromatic edge-to-face interactions, a series of four biaryl compounds containing a phenethyl side chain were prepared. These compounds exist as a slowly interconverting mixture of two atropisomers due to steric hindrance to rotation about the biaryl bond. The more thermodynamically stable isomer exhibits an abnormal shielding of an ortho-proton in solution indicative of an edge-to-face CH-pi interaction with the terminal phenyl ring on the side chain. This tilted-T type of geometry was observed in the X-ray crystal structure of one of the compounds. The edge-to-face conformation in solution is estimated by variable temperature NMR studies to be energetically favored by ca. 1.6 kcal mol(-1) but entropically disfavored by ca. 5.0 cal K-1 mol(-1).
  - DOI 10.1021/jo0520902
DA  - 2006/03
ER  - 

@article{V43336664,
   = {Jennings,  WB and Farrell,  BA and Malone,  JF },
   = {2006},
   = {March},
   = {The Journal of Organic Chemistry},
   = {Stereodynamics and edge-to-face CH-pi aromatic interactions in O-phenethyl-substituted biaryls},
   = {Validated},
   = {()},
   = {CRYSTAL-STRUCTURE SUPRAMOLECULAR STRUCTURES METAL-COMPLEXES CONFORMATION DERIVATIVES LIGANDS BINDING IMINES},
   = {71},
  pages = {2277--2282},
   = {{[GRAPHICS]As part of a search for systems that exhibit intramolecular aromatic edge-to-face interactions, a series of four biaryl compounds containing a phenethyl side chain were prepared. These compounds exist as a slowly interconverting mixture of two atropisomers due to steric hindrance to rotation about the biaryl bond. The more thermodynamically stable isomer exhibits an abnormal shielding of an ortho-proton in solution indicative of an edge-to-face CH-pi interaction with the terminal phenyl ring on the side chain. This tilted-T type of geometry was observed in the X-ray crystal structure of one of the compounds. The edge-to-face conformation in solution is estimated by variable temperature NMR studies to be energetically favored by ca. 1.6 kcal mol(-1) but entropically disfavored by ca. 5.0 cal K-1 mol(-1).}},
   = {DOI 10.1021/jo0520902},
  source = {IRIS}
}