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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 10
BKCSDE 28(10)
October 20, 2007

Title	Kinetics and Mechanism of the Addition of Anilines to β-Nitrostilbenes in Acetonitrile
Author	Dae Dong Sung*, Sang Soo Kang, Jong Pal Lee, Dae Il Jung, Zoon Ha Ryu, Ikchoon Lee
Keywords	β-Nitrostilbene, Addition reaction, Cross-interaction constant, Hydrogen-bonded TS, TS imbalance
Abstract	Addition reactions of anilines (XC₆H₄NH₂) to β-nitrostilbene (YC₆H₄CH=C(NO₂)C₆H₄Y') have been investigated in acetonitrile at 30.0 oC. The magnitude of βX values (=0.11-0.34) indicates relatively earlier transition state for additions with anilines than with benzylamines. The signs of ρY and ρY' are positive with Δρ = ρ_Y?ρ_Y' = 0.04, demonstrating a TS imbalance with a negative charge development on the C_β in the TS. The signs of cross-interaction constants ρ_XY (<0), ρ_XY' (<0) and ρ_YY' (>0) are consistent with bond forming and breaking processes. The relatively weak normal kinetic isotope effects involving deutarated nucleophiles, k_H/k_D>1, suggest an early, hydrogen-bonded, 4-member cyclic TS.
Page	1670 - 1674
Full Text	PDF

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