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Are the anions MeO(CO) (n = 1 and 2) methoxide anion donors in the gas phase? A theoretical investigation
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Are the anions MeO(CO) (n = 1 and 2) methoxide anion donors in the gas phase? A theoretical investigation

Tianfang Wang, P C H Eichinger, S Dua and J H Bowie
Rapid Communications in Mass Spectrometry, Vol.24(13), pp.1895-1901
2010
url
https://doi.org/10.1002/rcm.4586View
Published Version

Abstract

The anions CH3O--CO and CH3OCO--CO are both methoxide anion donors. The processes CH3O--CO → CH3O- + CO and CH3OCO-CO → CH3O- + 2CO have ΔG values of +8 and -68 kJ mol-1, respectively, at the CCSD(T)/6-311++G(2d, 2p)//B3LYP/6-311++G(2d,2p) level of theory. The reactions CH3OCOCO → CH3OCO + CO (ΔG = -22 kJ mol-1) and CH3COCH(O-)CO2CH3 → CH3COCH(O-)OCH3 + CO (ΔG = +19 kJ mol-1) proceed directly from the precursor anions via the transition states (CH3OCO…CO2)- and (CH3COCHO…CH3OCO)-, respectively. Anion CH3COCH(O-)CO2CH3 undergoes methoxide anion transfer and loss of two molecules of CO in the reaction sequence CH3COCH(O-)CO2CH3 → CH3CH(O-)COCO2CH3 → [CH3CHO (CH3OCO--CO)] → CH3CH(O-)OCH3 + 2CO (ΔG = +9 kJ mol-1). The hydride ion transfer in the first step is a key feature of the reaction sequence.

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