HYDROGEN ISOTOPE EFFECTS IN THE EQUILIBRIA BETWEEN 2,4-DINITROPHENOL AND AMINES
Spectrophotometric measurements show that in toluene solution triethylamine forms only hydrogen-bonded complexes with m-nitrophenol, p- nitrophenol, pentachlorophenol, and 2-bromo-5-nitrophenol, while proton transfer to give ion pairs takes place with o-nitrophenol and with 2,4-, 2,5-, and 2,6- dinitrophenol. The deuterium isotope effect was studied in toluene or chlorobenzene solution for the equilibria of 2,4-dinitrophenol with triethylamine, piperi dine, pyridine, and N,N-dimethylaniline. There is no detectable effect with triethylamine and piperidine, but with pyridine K/sub H//K/ sub D/ = 1.40 plus or minus 0.05; N,N-dimethylaniline probably occupies an intermediate position. The results can be accounted for quantitatively in terms of observed spectral frequencies and the occurrence of hydrogen bonding in the ion-pairs formed from weak bases. (auth)
- Research Organization:
- Oxford Univ.
- NSA Number:
- NSA-16-032992
- OSTI ID:
- 4777887
- Journal Information:
- Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc., Journal Name: Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc.; ISSN JCSOA
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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