Chemistry of 4-alkylaryloxenium ion "precursors": Sound and fury signifying something?

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 9954-9962

  Novak, Michael ^a   Brinster, Aaron M ^a   Dickhoff, Jill N ^a   Jones, Matthew P ^a   Leopold, Samuel H ^a   Vollman, Andrew T ^a   Wang, Yue Ting ^a   Glover, Stephen A ^b  

^a MIAMI UNIVERSITY   (United States)

^b UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER HYDROLYSIS; OXENIUM IONS;

CATALYSIS; HYDROLYSIS; IONS; REACTION KINETICS; SOLUTIONS;

ESTERS;

2 AZIDO 4 ISOPROPYLPHENOL; 2 AZIDO 4 TERT BUTYLPHENOL; 2,3,5,6 TETRAAZIDO 1,4 BENZOQUINONE; 3 AZIDO 4 ISOPROPYLPHENOL; 4 TERT BUTYLCRESOL; CRESOL; ESTER; ION; PHENOL DERIVATIVE; QUINONE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; DECOMPOSITION; HYDROLYSIS; KINETICS; OXIDATION;

EID: 37549062659     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701853e     Document Type: Article

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41. A reviewer has suggested that solvation effects might significantly alter the extrapolations of these kinetic correlations. In a preliminary study we added the AM1 SM5.4 aqueous solvation energies to the B3LYP/6-31G*//HF/6- 31G* energies of 1 and 6 in Scheme 6. The correlation of the four original ions was not significantly altered, and the long extrapolation to 1a-c led to modest changes in the estimated lifetime of these ions: 1.7 ps for 1a, 12.8 ps for 1b, and 3.3 ps for 1c. These lifetime estimates do not change our original conclusions.
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