Kinetic acidity of aliphatic hydrocarbons. Hydrogen isotope exchange with cesium cyclohexylamide in cyclohexylamine.
Kinetic acidities are reported for methane, ethane, propane, cyclopropane, isobutane, neopentane, tetramethylbutane, norbornane, nortricyclene, and adamantane by tritiodeprotonation or deuteriodeprotonation in cyclohexylamine catalyzed by cesium cyclohexylamide.
Streitwieser
Andrew
A
Department of Chemistry, University of California, Berkeley, California 94720-1460, USA. astreit@berkeley.edu
Keevil
Thomas A
TA
Taylor
David R
DR
Dart
Edward C
EC
D000577:Amides / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry*; D003514:Cyclohexylamines / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D041961:Deuterium Exchange Measurement / Q000379:methods; D006838:Hydrocarbons / Q000737:chemistry*; D007700:Kinetics; D009942:Organometallic Compounds / Q000737:chemistry*; D013997:Time Factors
D000577:Amides; D003514:Cyclohexylamines; D006838:Hydrocarbons; D009942:Organometallic Compounds; D002586:Cesium; D003903:Deuterium