Substituent chemical shift correlations. Proton magnetic resonance chemical shifts for N,N,N-trimethylphenylammonium iodides

Wiley, Gary R.; Miller, Sidney I.

doi:10.1021/jo00970a023

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1999

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Cited by 22 publications

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“…The product was recrystallized to a constant melting point, 157 -158 a (Lit., m.p. 156 -157 [8]). 4-dimethylaminobenzaldehyde was obtained commercially and was purified by recrystallization.…”

Section: Experimental Materialsmentioning

confidence: 99%

Kinetics and mechanism for oxime formation from 4-dimethylaminobenzaldehyde and 4-trimethylammoniobenzaldehyde iodide

Malpica

Calzadilla

Córdova

et al. 1999

Int. J. Chem. Kinet.

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The following lines of evidence establish that oxime formation from 4-dimethylaminobenzaldehyde and 4-trimethylammoniobenzaldehyde iodide occurs with a simple twostep mechanism. The pH-rate profile for the reaction of 4-trimethylammoniobenzaldehyde iodide exhibits, in order of decreasing pH, a negative deviation at pH near 2.0, corresponding to a transition from rate-determining step carbinolamine dehydration with acid catalysis to the uncatalyzed carbinolamine formation. In the case of the reaction of 4-dimethylaminobenzaldehyde, the pH-profile exhibits, in order of decreasing pH, a positive deviation at pH near 3.5 and then a negative deviation at pH near 2.0. These deviations have been interpreted in terms of i) transition of the rate-determining step, and ii) protolytic equilibrium of the substrate.

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Section: Experimental Materialsmentioning

confidence: 99%