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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 11
BKCSDE 32(11)
November 20, 2011 

Correlation of the Rates of Solvolysis of 1-Piperidincarbonyl Chloride Using the Extended Grunwald-Winstein Equation
Hojune Choi, Dildar Ali, Jong Pal Lee,*, Kiyull Yang, Jong Keun Park, In Sun Koo*
1-Piperidincarbonyl chloride (PCC), Grunwald-Winstein equation, Addition-elimination (A-E), Ionization (I), KSIE
The specific rates of sovolysis of 1-piperidincarbonyl chloride (1) have been determined in 26 pure and binary solvents at 25.0 oC. Comparison of the specific rates of solvolyses of 1 with those for p-methoxybenzoyl chloride and those for 4-morpholinecarbonyl chloride in terms of linear free energy relationships (LFER) are helpful in mechanistic considerations, as is also treatment in terms of the extended Grunwald-Winstein equation. It is proposed that the solvolyses of 1 in binary aqueous solvent mixtures proceed through an ionization [I] pathway rather than through an SN1/SN2 and/or ionization/(ionization-elimination) = [I/(I−E)] pathway.
3941 - 3946
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