Cross interaction constants as a measure of the transition state structure (part III). Mechanism of reactions between 1‐phenylethyl benzenesulfonates with N,N‐dimethylanilines | Zendy

Lee Ikchoon | Zendy; Kim Hyung Yoon | Zendy; Lee Hai Whang | Zendy; Kim In Chul | Zendy

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Cross interaction constants as a measure of the transition state structure (part III). Mechanism of reactions between 1‐phenylethyl benzenesulfonates with N,N‐dimethylanilines

Author(s) -

Lee Ikchoon,

Kim Hyung Yoon,

Lee Hai Whang,

Kim In Chul

Publication year - 1989

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.610020105

Subject(s) - chemistry , nucleophile , leaving group , reactivity (psychology) , hydrogen bond , methanol , medicinal chemistry , selectivity , nucleophilic substitution , photochemistry , computational chemistry , stereochemistry , catalysis , organic chemistry , molecule , medicine , alternative medicine , pathology

The kinetics and mechanisms of the reactions between 1‐phenylethyl benzenesulfonates (1‐PEB) with N,N‐dimethylanilines are investigated in methanol at 35·0°C. Reactivity and selectivity trends were found to be similar to those for the reactions of 1‐PEB with anilines, but the magnitudes of cross interaction constants, ρXZ, between substituents X in the nucleophile and Z in the leaving group were substantially smaller indicating no hydrogen‐bond bypass bridge formation in the transition state. However, the magnitude of ρXZ suggested a direct electrostatic interaction between the reaction centers in the nucleophile and leaving group in the frontside nucleophilic attack with a loose transition state structure.

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