Abstract
WE are sorry to have again to contradict Dr. Evans, but he continues to misrepresent us1. He does so now by quoting a limited passage from a paper by one of us2, and then adding, as though it were a paraphrase, a statement of his own that does not, in fact, reproduce the meaning. The passage is dealing with the relative rates of nucleophilic halogen substitution in R-Hal, where R = Me, Et, n-Pr, i-Bu, neoPentyl, and, as quoted, reads : “The rate relationships for the first four members are fairly normal for the bimolecular mechanism, the rate of which is decreased by electron-accession to the reaction centre, but the introduction of the last B-methyl substituent has obviously introduced an effect which is far larger than that to be expected on the basis of its capacity for the release of electrons. . . This effect is believed to be of steric origin.” Dr. Evans continues : “This indicates that steric hindrance was considered to be unimportant in the bimolecular SN2 reactions of RX when R is methyl or ethyl”. On the contrary, it “indicates” what it states, namely, that the total structural effect on rate when R = neopentyl is in fact far greater than in the other cases, that Hughes could not see why the polar effect of methyl should take such a sudden jump as the last methyl is introduced, and that he could see a reason why its steric effect might do so.
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Evans, A. G., Nature, 158, 586 (1946); cf. ibid., 157, 438 (1946); cf. also Hughes and Ingold, ibid., 158, 94 (1946).
Hughes, Trans. Farad. Soc., 37, 621 (1941).
Hughes and Ingold, ref. 1.
Trans. Farad. Soc., 37, 377 (1941).
Ref. 2. Cf. Dostrovsky, Hughes and Ingold, J. Chem. Soc., 173 (1946).
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HUGHES, E., INGOLD, C. Reactions of Organic Halides in Solution. Nature 159, 166 (1947). https://doi.org/10.1038/159166a0
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DOI: https://doi.org/10.1038/159166a0
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