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Volumn 4, Issue 12, 2009, Pages 1824-1829

Kinetics of hydride abstractions from 2-arylbenzimidazolines

Author keywords

Carbocations; Hydride transfer; Intrinsic barrier; Linear free energy relationships; Nucleophilicity

Indexed keywords

CARBOCATIONS; HYDRIDE TRANSFERS; INTRINSIC BARRIERS; LINEAR FREE ENERGY RELATIONSHIPS; NUCLEOPHILICITIES;

EID: 73649117812     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900322     Document Type: Article
Times cited : (28)

References (78)
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    • During our attempts to elucidate the origin of this curvature, we have studied the kinetics of the reactions of 1d with 3b-d in the presence of 1,2,4,5-tetramethylbenzene (1.0 equiv with respect to 1d). Under these conditions, the plots of kobs vs. [1d] became linear, and the slopes corresponded to the initial slopes of the correlations without an additive (Figure S4 on page S11 in the Supporting Information)
    • During our attempts to elucidate the origin of this curvature, we have studied the kinetics of the reactions of 1d with 3b-d in the presence of 1,2,4,5-tetramethylbenzene (1.0 equiv with respect to 1d). Under these conditions, the plots of kobs vs. [1d] became linear, and the slopes corresponded to the initial slopes of the correlations without an additive (Figure S4 on page S11 in the Supporting Information)
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    • this deviation would become even more severe when σ+ instead of σ values would be used on the abscissa
    • this deviation would become even more severe when σ+ instead of σ values would be used on the abscissa.
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    • Because of the greater value of s for the Hantzsch ester 2a, the relative reactivities will invert for reactions with highly electrophilic carbenium ions
    • Because of the greater value of s for the Hantzsch ester 2a, the relative reactivities will invert for reactions with highly electrophilic carbenium ions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.