Persistent Intramolecular C-H···X (X = O or S) Hydrogen-Bonding in Benzyl Meldrum's Acid Derivatives.
C-H···X (where X = O or S) intramolecular hydrogen bonding is investigated in three benzyl Meldrum's acid derivatives using a combination of solution phase NMR spectroscopy, gas phase infrared multiple photon dissociation spectroscopy, and density functional theory calculations. In one compound, an abnormally large C-H···S hydrogen bond energy of 30.4 kJ mol-1is calculated with a natural bond orbital analysis. Intramolecular C-H···O hydrogen bonding is found to persist in the gas phase. Gibbs energy decomposition pathways are calculated.
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
W Scott
WS
Hopkins
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
Moaraj
M
Hasan
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
Michael
M
Burt
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
Rick A
RA
Marta
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
Eric
E
Fillion
Department of Chemistry, University of Waterloo , Waterloo, ON, Canada , N2L 3G1.
Terry B
TB
McMahon