KCS Publications

HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 5
BKCSDE 27(5)
May 20, 2006

Title	Kinetic and Mechanism of the Addition of Benzylamines to α-Phenyl-β-thiophenylacrylonitriles in Acetonitrile
Author	Jaeyoung Hwang, Kiyull Yang, In Sun Koo*, Dae Dong Sung, Ikchoon Lee
Keywords	Nucleophilic addition reaction, Cross-interaction constant, Kinetic isotope effects, Four-center cyclic transition state
Abstract	Nucleophilic addition reactions of p-substitutedbenzylamines (XC₆H₄CH₂NH₂) to α-phenyl-β-thiophenylacrylonitriles (YC₄SH₂CH=C(CN)C₆H₄Y') have been studied in acetonitrile at 25.0, 30.0, and 35.0 ^oC. The reactions take place in single step in which the Cβ -N bond formation and proton transfer to Cα of α-phenyl-β-thiophenylacrylonitriles occur concurrently with four-membered cyclic transition structure. These mechanistic conclusions are drawn based on (i) the large negative ρ_X and large positive ρ_Y' values and also large magnitude of ρ_X, (ii) the negative sign and large magnitude of the cross-interaction constants (ρ_XY), (iii) the normal kinetic isotope effects (k_H/k_D > 1.0), and (iv) relatively low ΔH^≠ and large negative ΔS^≠ values.
Page	733 - 738
Full Text	PDF

How to access to the WOL for The Bulletin of the Korean Chemical Society ?

The Bulletin of the Korean Chemical Society will be co-published with Wiley-VCH from 2015 towards. The online version of the Journal will thus be available on Wiley Online Library, Wiley(-VCH)'s global online platform.

KCS members can get a free online access to the Bulletin of the Korean Chemical Society in WOL.

Free Access to WOL