An electron diffraction investigation of the molecular structure of formic acetic anhydride

Vledder, H.J.; Mijlhoff, F.C.; Well, F.P. Van; Dofferhoff, G.M.T.; Leyte, J. C.

doi:10.1016/0022-2860(71)85004-4

Cited by 11 publications

(2 citation statements)

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“…In fact, ∆ did not change when in FAA the CH 3 group was replaced by CD 3 . 6 Next, comparison of FAA force constants with those of FA 1 reveals that C(2)-O(1) and C(8)-O( 1) have more single-bond character (5,4,6)+θ (5,4,7)+θ (6,4,7) a r(i,j) bond distance between atoms i and j; θ(i,j,k), valence angle between atoms i, j, and k; χ(i,j,k,l), out-of-plane deformation of atom i out of j,k,l plane; ι(i,j,k,l), torsion angle between atoms i,j,k,l along bond j,k. See Figure 1 for atomic numbering scheme.…”

Section: Vibrational Spectroscopymentioning

confidence: 99%

“…So far a review, 4 mostly on the chemical properties of FAA, has been published, but few structural studies of mixed anhydrides of formic and other open chain carboxylic acids have appeared. Earlier electron diffraction data of FAA have been interpreted 5 to show the existence of one nonplanar conformer with torsion angles φ1 ) 46(3)°and φ2 ) 159(3)°, i.e. an (sc,ap) conformation.…”

Section: Introductionmentioning

confidence: 99%

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Formic Acetic Anhydride in the Gas Phase, Studied by Electron Diffraction and Infrared Spectroscopy, Supplemented with ab-Initio Calculations of Geometries and Force Fields

Wu¹,

Shlykov²,

Alsenoy³

et al. 1996

J. Phys. Chem.

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The structure of formic acetic anhydride was studied by the joint analysis of gas-phase electron diffraction and infrared data, supported with extensive ab-initio calculations on the 4-21G and 6-31G** levels. All data agree with the gas phase at room temperature existing in the planar (sp,ap) conformer. Best electron diffraction geometry was obtained using geometrical constraints derived from 4-21G calculations after correction to r α° level. Also, the scaled 4-21G force field performed better than its 6-31G** counterpart. The new model of formic acetic anhydride is self-consistent, reproduces the IR frequencies with a root-mean-square deviation of 8.8 cm-1, and results in an improved frequency assignment as well as in a good qualitative agreement between observed and calculated IR band intensities. Formic acetic anhydride is conformationally and spectroscopically very different from acetic anhydride, but strongly resembles formic anhydride, although differences remain. The similarities with formic anhydride are ascribed to an attractive nonbonded H (formyl)···O= interaction, while the dissimilarities are ascribed to a larger electronic interaction between two formyl moieties rather than between a formyl and an acetyl moiety.

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