A DFT and AIM analysis of the spin–spin couplings across the hydrogen bond in the 2‐fluorobenzamide and related compounds |
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| Authors: | Ibon Alkorta José Elguero Hans‐Heinrich Limbach Ilja G. Shenderovich Tammo Winkler |
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| Affiliation: | 1. Instituto de Química Médica, CSIC, Juan de la Cierva 3, E‐28006 Madrid, Spain;2. Institut für Chemie and Biochemie, Takustrasse 3, Freie Universit?t Berlin, D‐14195 Berlin, Germany;3. Solvias AG, Klybeckstrasse 191, 4057 Basel, Switzerland |
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| Abstract: | In 1975 a large number of coupling constants were measured in 2‐fluorobenzamide labeled with 15N. Some of them were assigned to couplings through intramolecular N? H···F hydrogen bonds (HBs). These couplings change dramatically when CDCl3 is replaced by DMSO‐d6. 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. |
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| Keywords: | 2‐fluorobenzamide hydrogen bonds solvent effects spin‐spin coupling constants B3LYP/6‐311 + + G** AIM |
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