Carbon-13 and fluorine-19 nuclear magnetic resonance chemical shift studies of carbon-13 enriched p-fluorobenzoyl derivatives

Spratt, M. P.; Armistead, D.; Motell, Edwin L.; Dorn, Harry C.

doi:10.1021/ac00279a080

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Derivatizing Reagents (Drs)1

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1987

2009

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Cited by 3 publications

(1 citation statement)

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“…Nevertheless, with complex mixtures and large size substrates, spectral overlap can still be troublesome, in a model study of alcohols, phenols and amine derivatives, the problem was overcome by enriching the carbonyl carbon of the p-fluorobenzoyl chloride tagging reagent to a level of 90% with the isotope [85].…”

Section: Derivatizing Reagents (Drs)mentioning

confidence: 99%

Organic analytical reagents in nuclear magnetic resonance spectroscopy

Flockhart¹,

Burns²

1987

Pure and Applied Chemistry

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Section: Derivatizing Reagents (Drs)mentioning

confidence: 99%

Organic analytical reagents in nuclear magnetic resonance spectroscopy

Flockhart¹,

Burns²

1987

Pure and Applied Chemistry

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NMRSpectroscopy

Taylor

Everatt²

2009

Patai's Chemistry of Functional Groups

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The collision induced loss of carbon monoxide from deprotonated benzyl benzoate in the gas phase. An anionic 1,2-Wittig type rearrangement

Chia¹,

Taylor²,

Dua³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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The ion PhCO 2 ᎐ ؊ CHPh, upon collision activation, undergoes competitive losses of CO and CO 2 of which the former process produces the base peak of the spectrum. Product ion and substituent effect (Hammett) studies indicate that PhCO 2 ᎐ ؊ CHPh cyclises to a deprotonated hydroxydiphenyloxirane which ring opens to PhCOCH(O ؊ )Ph. This anion then undergoes an anionic 1,2-Wittig type rearrangement {through [PhCO ؊ (PhCHO)]} to form Ph 2 CHO ؊ and CO. The mechanism of the 1,2-rearrangement has been probed by an ab initio study [at MP4(SDTQ)/6-31؉؉G(d,p) level] of the model system HCOCH 2 O ؊ → MeO ؊ ؉ CO. The analogous system RCO 2 ᎐ ؊ CHPh (R ‫؍‬ alkyl) similarly loses CO, and the migratory aptitudes of the alkyl R groups in this reaction are Bu t > Me > Et ~Pr i ). This trend correlates with the order of anion basicities (i.e. the order of G o acid values of RH), supporting the operation of an anion migration process. The loss of CO 2 from PhCO 2 ᎐ ؊ CHPh yields Ph 2 CH ؊ as the anionic product: several mechanistic scenarios are possible, one of which involves an initial ipso nucleophilic substitution.

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Carbon-13 and fluorine-19 nuclear magnetic resonance chemical shift studies of carbon-13 enriched p-fluorobenzoyl derivatives

Cited by 3 publications

References 10 publications

Organic analytical reagents in nuclear magnetic resonance spectroscopy

Organic analytical reagents in nuclear magnetic resonance spectroscopy

NMRSpectroscopy

The collision induced loss of carbon monoxide from deprotonated benzyl benzoate in the gas phase. An anionic 1,2-Wittig type rearrangement

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