Rotational Spectrum and Internal Dynamics of Methylpyruvate

Velino, Biagio; Favero, Laura B.; Ottaviani, Paolo; Maris, Assimo; Camináti, Walther

doi:10.1021/jp310074z

Cited by 9 publications

(5 citation statements)

References 26 publications

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“…This indicates that there is not much difference in the electronic and steric environment around the ester methyl group in both conformers. These barriers are also quite similar in magnitude to the related ester methyl group barriers of other methyl carboxylates, such as methyl lactate (4.76 kJ/mol), methyl pyruvate (4.883 kJ/mol) . and methyl acetate (5.0500 kJ/mol) …”

Section: Results and Disscussionssupporting

confidence: 61%

“…Esters in general are also of spectroscopic interest because of the internal rotation motion of the methyl tops. Rotational or ro-vibrational spectra of a few small to midsize esters containing one or two methyl tops have been reported previously. ,− For example, internal rotation splittings due to one or two methyl rotors were detected and analyzed in methyl salycylate, methyl lactate, methyl acetate, methyl difluoroacetate, and methyl pyruvate . In this paper we report a detailed high resolution rotational spectroscopic study of methyl glycidate and all its singly substituted 13 C isotopologues of the most stable conformer using a broad-band chirped-pulse Fourier transform microwave (FTMW) and a narrow-band cavity FTMW spectrometer.…”

Section: Introductionmentioning

confidence: 73%

“…These barriers are also quite similar in magnitude to the related ester methyl group barriers of other methyl carboxylates, such as methyl lactate (4.76 kJ/mol), 9 methyl pyruvate (4.883 kJ/mol). 17 and methyl acetate (5.0500 kJ/mol). 14…”

Section: ■ Results and Disscussionsmentioning

confidence: 99%

“…9,11−17 For example, internal rotation splittings due to one or two methyl rotors were detected and analyzed in methyl salycylate, 13 methyl lactate, 9 methyl acetate, 14 methyl difluoroacetate, 15 and methyl pyruvate. 17 In this paper we report a detailed high resolution rotational spectroscopic study of methyl glycidate and all its singly substituted 13 C isotopologues of the most stable conformer using a broad-band chirped-pulse Fourier transform microwave (FTMW) and a narrow-band cavity FTMW spectrometer. Methyl glycidate is a versatile chiral building block used in syntheses of many important organic molecules.…”

Section: ■ Introductionmentioning

confidence: 99%

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Chirped-Pulse and Cavity-Based Fourier Transform Microwave Spectroscopy of a Chiral Epoxy Ester: Methyl Glycidate

et al. 2013

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Rotational spectra of a chiral epoxy ester, methyl glycidate, were measured using a chirped-pulse and a cavity-based Fourier transform microwave spectrometer. The two lowest energy conformers where the epoxy oxygen and the ester oxygen atoms are in the syn and anti relative orientation with respect to each other were identified experimentally. Spectra of four (13)C isotopologues of the lowest energy conformer of methyl glycidate were also measured and assigned. All of the observed rotational transitions are split into doublets due to the presence of the ester methyl internal rotor. The rotational constants and the internal rotation barrier height for the ester methyl group were determined for both conformers of methyl glycidate and for the four (13)C isotopologues of the most stable conformer. A value for the interconversion barrier between the two most stable conformers was estimated. Furthermore, comparison to strawberry aldehyde, a larger derivative of methyl glycidate, shows how the syn-anti conformational equilibrium shifts as a result of the additional bulky substituents at the epoxy ring and at the ester oxygen atom.

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Section: Results and Disscussionssupporting

confidence: 61%