Hydrogen Bonding in the Gas-Phase: The Molecular Structures of 2‑Hydroxybenzamide (C<sub>7</sub>H<sub>7</sub>NO<sub>2</sub>) and 2‑Methoxybenzamide (C<sub>8</sub>H<sub>9</sub>NO<sub>2</sub>), Obtained
by Gas-Phase Electron Diffraction and Theoretical Calculations
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Abstract
The
structures of 2-hydroxybenzamide (C<sub>7</sub>H<sub>7</sub>NO<sub>2</sub>) and 2-methoxybenzamide (C<sub>8</sub>H<sub>9</sub>NO<sub>2</sub>) have been determined in the gas-phase by electron diffraction
using results from quantum chemical calculations to inform restraints
used on the structural parameters. Theoretical methods (HF and MP2/6-311+G(d,p))
predict four stable conformers for both 2-hydroxybenzamide and 2-methoxybenzamide.
For both compounds, evidence for intramolecular hydrogen bonding is
presented. In 2-hydroxybenzamide, the observed hydrogen bonded fragment
is between the hydroxyl and carbonyl groups, while in 2-methoxybenzamide,
the hydrogen bonded fragment is between one of the hydrogen atoms
of the amide group and the methoxy oxygen atom
