Molecular Orbital Studies of the Protonation of the Methylanisoles

Raymond S. Greenberg; Maurice M. Bursey; Lee G. Pedersen

doi:10.1021/ja00430a007

Molecular Orbital Studies of the Protonation of the Methylanisoles

Raymond S. Greenberg, Maurice M. Bursey, Lee G. Pedersen

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Application of the STO-3G method to the energetics of protonation of the ambident methylanisoles shows the predominance of ring protonation for all three isomers. The method further indicates that oxygen protonation is only competitive for the para isomer. Comparison of these results with those for the methylphenols allows prediction of differences between the hydroxy and methoxy substituents in a typical system, and the predictions are in close accord with experimentally well known trends.

Original language	English (US)
Pages (from-to)	4061-4064
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	98
Issue number	14
DOIs	https://doi.org/10.1021/ja00430a007
State	Published - Jul 1 1976
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "Application of the STO-3G method to the energetics of protonation of the ambident methylanisoles shows the predominance of ring protonation for all three isomers. The method further indicates that oxygen protonation is only competitive for the para isomer. Comparison of these results with those for the methylphenols allows prediction of differences between the hydroxy and methoxy substituents in a typical system, and the predictions are in close accord with experimentally well known trends.",

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AU - Pedersen, Lee G.

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N2 - Application of the STO-3G method to the energetics of protonation of the ambident methylanisoles shows the predominance of ring protonation for all three isomers. The method further indicates that oxygen protonation is only competitive for the para isomer. Comparison of these results with those for the methylphenols allows prediction of differences between the hydroxy and methoxy substituents in a typical system, and the predictions are in close accord with experimentally well known trends.

AB - Application of the STO-3G method to the energetics of protonation of the ambident methylanisoles shows the predominance of ring protonation for all three isomers. The method further indicates that oxygen protonation is only competitive for the para isomer. Comparison of these results with those for the methylphenols allows prediction of differences between the hydroxy and methoxy substituents in a typical system, and the predictions are in close accord with experimentally well known trends.

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Molecular Orbital Studies of the Protonation of the Methylanisoles

Abstract

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