Hydrogen Bonding in the Gas-Phase: The Molecular Structures of 2-Hydroxybenzamide (C7H7NO2) and 2-Methoxybenzamide (C8H9NO2), Obtained by Gas-Phase Electron Diffraction and Theoretical Calculations | Zendy

Kirsten Aarset | Zendy; E. M. Page | Zendy; David A. Rice | Zendy

Open Access

Hydrogen Bonding in the Gas-Phase: The Molecular Structures of 2-Hydroxybenzamide (C₇H₇NO₂) and 2-Methoxybenzamide (C₈H₉NO₂), Obtained by Gas-Phase Electron Diffraction and Theoretical Calculations

Author(s) -

Kirsten Aarset,

E. M. Page,

David A. Rice

Publication year - 2013

Publication title -

the journal of physical chemistry a

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.756

H-Index - 235

eISSN - 1520-5215

pISSN - 1089-5639

DOI - 10.1021/jp311003d

Subject(s) - hydrogen bond , chemistry , intramolecular force , crystallography , amide , hydrogen , gas phase , stereochemistry , molecule , organic chemistry

The structures of 2-hydroxybenzamide (C7H7NO2) and 2-methoxybenzamide (C8H9NO2) 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.

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