1993
DOI: 10.1021/j100143a024
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Molecular structure and conformation of gas-phase methyl dichloroacetate

Abstract: Gas-phase electron diffraction data obtained a t 22-23 OC, together with a b initio calculations, have been used to determine the structure and conformational composition of methyl dichloroacetate (HC12C-C-(=O)-o-CH3).Two conformers have been identified, 53 (13)% of a syn form with a H-C-C=O torsion angle of $1 = 0' and 47 (1 3)% of a gauche form with $1 = 152 (5)O. For both conformers the O=C-O-CH3 torsional angle was found to be $2 = Oo. Results obtained for the bond distances (rg) and valence angles (La)for… Show more

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Cited by 7 publications
(4 citation statements)
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“…r(C@O) is calculated shorter than the experimental value, but this has been observed in many of these molecules. The OACH 3 bond distance is found to be surprisingly long, both compared with calculated values and with experimental values observed in related molecules [12,13]. We have no good explanation for this.…”
Section: Discussioncontrasting
confidence: 53%
“…r(C@O) is calculated shorter than the experimental value, but this has been observed in many of these molecules. The OACH 3 bond distance is found to be surprisingly long, both compared with calculated values and with experimental values observed in related molecules [12,13]. We have no good explanation for this.…”
Section: Discussioncontrasting
confidence: 53%
“…As shown in Figures 1 and S1, the methyldichloroacetate (MDCA) is having two conformers, cis and trans, that are formed due to the internal rotation around the C1−C2 bond, i.e., dihedral angle, (H1−C1−C2−O1) of MDCA. The energy calculated for optimized geometry of cis and trans conformers show that the cis conformer is the most stable conformer by 3 kcal/mol, which is in agreement with the earlier studies of Olega et al 30 Hence, the reaction of MDCA with OH radical is studied with cis conformer.…”
Section: Resultsmentioning
confidence: 99%
“…Rotational isomerism in several α-halo-substituted acetic acids and their derivatives has been intensively studied by ab initio, spectroscopic, and diffraction methods. With regard to 2,2-dichloroacetic acid, its methyl ester, and acyl chloride, several studies indicate clearly the presence of two low-energy conformers derived from rotational isomerism of the dichloromethyl group. They are syn conformers in which the HCCO torsion angle is ∼0°, and gauche conformers in which this torsion angle is ∼140° (with eclipsing of Cl and O atoms).…”
Section: Introductionmentioning
confidence: 99%
“…Rotational isomerism in several R-halo-substituted acetic acids and their derivatives has been intensively studied by ab initio, spectroscopic, and diffraction methods. [1][2][3][4][5][6] With regard to 2,2dichloroacetic acid, 7 its methyl ester, 8 and acyl chloride, 9 several studies indicate clearly the presence of two low-energy conformers derived from rotational isomerism of the dichloromethyl group. They are syn conformers in which the HCCO torsion angle is ∼0°, and gauche conformers in which this torsion angle is ∼140°(with eclipsing of Cl and O atoms).…”
Section: Introductionmentioning
confidence: 99%