32. The kinetics of the alkaline hydrolysis of esters and amides of 1- and 2-naphthoic acid

Fitzgerald, Peter; Packer, John E.; Vaughan, James R.; Wilson, A. F.

doi:10.1039/jr9560000170

Cited by 4 publications

(2 citation statements)

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“…Reactions 1-9 are reactions of anilines, phenols, or their derivatives; reactions 10-13 cover carbinyl chloride solvolyses; reactions not entering either of the first two categories are those numbered 14-26. It is clear that reactions [14][15][16][17][18][19][20][21][22][23][24][25][26] are those which should require normal values; reactions 10-13 presumably demand + values, and to reactions 1-9 ~values should apply. The calculated values do indeed group themselves accordingly, although the substituent constants for phenol and amine reactions (1-9) are less internally consistent (see later, however).…”

Section: Discussionmentioning

confidence: 99%

The Substituent Constant of the 3,4-Benzo Group

Fischer¹,

Packer²,

Vaughan³

et al. 1959

J. Org. Chem.

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SUBSTITUENT CONSTANT OF THE 3,4-BENZO GROUP 155Stirring was continued at reflux for 5 hr. and the bromide was then recovered in the usual way. The recovered bromide showed a slight increase in the amount of trans isomer, as evidenced by the diagnostic infrared bands of the latter, but was still very predominantly cis.(c) The above experiment was repeated, expect that pure as-bromide was used and the bromide was added to the silver acetate suspension one minute before bromine addition commenced. In this way, the cis-bromide was exposed to both bromine and silver bromide under the reaction conditions, rather than to silver bromide only. After 1 hr. boiling at reflux with stirring, the mixture was worked up as previously described. The product showed a marked ester band in the infrared at 5.77µ and very weak bands ascrib-able to the irons isomer, the one at 11.4µ being the most prominent (about six scale divisions). However, the recovered material was still very largely as-bromide.

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Section: Discussionmentioning

confidence: 99%

The Substituent Constant of the 3,4-Benzo Group

Fischer¹,

Packer²,

Vaughan³

et al. 1959

J. Org. Chem.

Self Cite

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show abstract

“…Otherwise the effect of the 8-nitro group should, of course, be relayed (by resonance) to the /3-carbon atom on the ring more effectively than that of a -nitro group (which acts by an inductive effect only) (482). Additional papers (211,212,214,469) have been published on the kinetics of hydrolysis of substituted 1as well as 2-naphthoates. Both ethyl and methyl esters of 1-naphthoic acid are found to undergo hydrolysis slower than their 2 isomers.…”

Section: CLXIVmentioning

confidence: 99%