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A DFT and AIM analysis of the spin–spin couplings across the hydrogen bond in the 2‐fluorobenzamide and related compounds
Author(s) -
Alkorta Ibon,
Elguero José,
Limbach HansHeinrich,
Shenderovich Ilja G.,
Winkler Tammo
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2433
Subject(s) - intramolecular force , chemistry , hydrogen bond , density functional theory , computational chemistry , spin (aerodynamics) , solvent , molecule , coupling constant , atoms in molecules , hydrogen , crystallography , stereochemistry , thermodynamics , organic chemistry , quantum mechanics , physics
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 NH···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. Copyright © 2009 John Wiley & Sons, Ltd.