1977
DOI: 10.1021/ja00456a009
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Gas-phase basicities of substituted anilines. Inferences about the role of solvent in dictating site of protonation

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Cited by 57 publications
(18 citation statements)
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“…These include aniline, the toluidines, m-arusidine ( Figure 4), and m-ammophenol. It should be noted that these compounds are all examples where the r~g proton affinity and the N-proton affinity are very sirrular [37,47,48]. It is not clear whether this extra exchange indicates that HID exchange occurs by~O…”
Section: Resultsmentioning
confidence: 97%
“…These include aniline, the toluidines, m-arusidine ( Figure 4), and m-ammophenol. It should be noted that these compounds are all examples where the r~g proton affinity and the N-proton affinity are very sirrular [37,47,48]. It is not clear whether this extra exchange indicates that HID exchange occurs by~O…”
Section: Resultsmentioning
confidence: 97%
“…16 We have observed the substitution reaction in the NH3 CI spectra of some alcohols, halides, TMS ethers, acetates and acetals. The results obtained for acetals are particularly interesting; a typical spectrum is given in Fig.…”
Section: Substituent Effects On the Substitution Reactionmentioning
confidence: 91%
“…A detailed comparison 53 of the gas-phase and aqueous-phase basicities of substituted pyridines has concluded that polarizability effects of substituents are absent in solution and that the gas-phase data when corrected for polarizability contributions correlate with the solution data, although there is an attenuation of the effect of substituents in the aqueous phase. 54 have presented evidence that m-methoxyaniline and mmethylaniline are preferentially protonated on the ring rather than the nitrogen, while Lau et al 55 have presented evidence that the m-amino-, m-methoxy-and m-thiomethoxyanilines are protonated on the ring rather than the nitrogen. The results in Fig.…”
Section: Methodsmentioning
confidence: 99%