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Differences among the mechanisms of reaction of phenylhydroxylamine with various carbonyl compounds

✍ Scribed by I. M. C. Brighente; R. Menegatti; R. A. Yunes

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 118 KB
Volume: 32
Category: Article
ISSN: 0538-8066
DOI: 10.1002/1097-4601(2000)32:8<453::aid-kin1>3.0.co;2-k

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✦ Synopsis

In order to obtain a better knowledge of the special behavior of phenylhydroxylamine as a nucleophile, the mechanism of its reaction with 2,6-dichlorobenzaldehyde, norcamphor, and cyclohexanone, and also the hydrophobic effect on its reaction with 2,6-dichlorobenzaldehyde and benzaldehyde, was studied. The results led us to assume that the planar molecule of phenylhydroxylamine should be placed parallel to the planar molecule of benzaldehyde in order to permit the attack of the lone electron pair of the nitrogen on the carbonyl group, forming, together with a hydrogen bond between the hydroxyl group and the carbonylic oxygen atom, a packed preassociation complex. This mechanism is not observed in the case of norcamphor or 2,6-dichlorobenzaldehyde due to the steric hindrances produced by the lack of planarity of these molecules.

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