Microwave spectrum and the structure of benzoyl chloride

Onda, Masao; Asai, Motoo; Kohno, Toshiya; Kikuchi, Yasuhiro; Yamaguchi, Iwao

doi:10.1016/0022-2860(87)87051-5

Cited by 16 publications

(2 citation statements)

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“…A study of 2-chloro-1-phenylethanone, ClH 2 CC(O)Ph (phenacyl chloride), was therefore undertaken. Other molecules where a carbonyl group is attached to a phenyl ring have also been investigated earlier (PhC(O)X, with X = H, Cl, C(O)H, C(O)CH 3 , or C(O)Ph), and our results for 2-chloro-1-phenylethanone are compared with some of these earlier results.…”

Section: Introductionsupporting

confidence: 52%

“…In addition to the different possible positions of CO relative to CCl, the molecule may also have different positions for the CO bond relative to the phenyl group. In earlier studies of similar molecules, − it was found that CO normally is coplanar or nearly coplanar with the phenyl group, possibly because of the effect of conjugation between the phenyl ring and the carbonyl group in a planar conformation. Both MP2 and HF calculations also indicated that the CO bond is nearly coplanar with the phenyl group.…”

Section: Discussionmentioning

confidence: 98%

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Molecular Structure and Conformational Composition of 2-Chloro-1-phenylethanone, ClH₂CC(O)Ph, Obtained Using Gas-Phase Electron-Diffraction Data and Results from Theoretical Calculations

Aarset

Hagen

2005

J. Phys. Chem. A

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The structure and conformation of 2-chloro-1-phenylethanone, ClH(2)C-C(=O)Ph (phenacyl chloride), have been determined by gas-phase electron diffraction (GED), augmented by results from ab initio molecular orbital calculations, employing the second-order Møller-Plesset (MP2) level of theory and the 6-311+G(d) basis set. The molecules may exist as a mixture of different conformers with the C-Cl bond either syn (torsion angle phi = 0 degrees ) or gauche to the carbonyl bond. At 179 degrees C, the majority of the molecules (90 +/- 11%) have the gauche conformation (phi = 112(3) degrees). Torsion is also possible about the C-Ph single bond. Both experimental and theoretical data indicated, however, that the phenyl ring is coplanar or nearly coplanar with the carbonyl group. The results for the principal distances (r(g)) and angles (angle(alpha)) for the gauche conformer from a combined GED/ab initio study (with estimated 2sigma uncertainties) are the following: r(C-C)(phenyl) = 1.394(2) (average value) A, r(C(phenyl)-C(carbonyl)) = 1.484(5) A, r(C(carbonyl)-C(alkyl)) = 1.513(5) A, r(C-Cl) = 1.790(5) A, r(C=O) = 1.218(6) A, r(C-H)(phenyl) = 1.087(9) (average value) A, r(C-H)(alkyl) = 1.090(9) A (average value), angle C(phenyl)-C=O = 119.5(9) degrees, angle C(phenyl)-C(carbonyl)-C(alkyl) = 119.2(10) degrees, angle C-C-Cl = 109.8(12) degrees, angle C(2)-C(1)-C(carbonyl) = 122.8(15) degrees, angle C-C(alkyl)-H = 111.2 degrees (ab initio value).

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