A DFT and AIM analysis of the spin-spin couplings across the hydrogen bond in the 2-fluorobenzamide and related compounds.
In 1975 a large number of coupling constants were measured in 2-fluorobenzamide labeled with (15)N. Some of them were assigned to couplings through intramolecular N-H...F hydrogen bonds (HBs). These couplings change dramatically when CDCl(3) is replaced by DMSO-d(6). In this theoretical paper we provide density functional theory (DFT) calculations that justify the existence of a weak HB in the absence of solvent, while solvents that act as HB acceptors break down the intramolecular hydrogen bond (IMHB) of 2-fluorobenzamide. Atoms in molecules (AIM) analyses and Steiner-Limbach plots were used to analyze the structure of the compounds.
Alkorta
Ibon
I
Instituto de Química Médica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain. ibon@iqm.csic.es
Elguero
José
J
Limbach
Hans-Heinrich
HH
Shenderovich
Ilja G
IG
Winkler
Tammo
T
D001549:Benzamides / Q000737:chemistry*; D006860:Hydrogen Bonding; D008432:Mathematical Computing; D012997:Solvents / Q000737:chemistry*
C542690:2-fluorobenzamide; D001549:Benzamides; D012997:Solvents