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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 6
BKCSDE 33(6)
June 20, 2012 

 
Title
Comparative Studies on the Reactions of Carbamyl and Thiocarbamyl Halides with NH3 in the Gas Phase and in Aqueous Solution: A Theoretical Study
Author
Chang Kon Kim, In Suk Han, Chang Kook Sohn, Yu Hee Yu, Zhishan Su, Chan Kyung Kim*
Keywords
Aminolyses of carbamyl and thiocarbamyl halides, Stability of tetrahedral structures, Deformation energy, Double bond strength
Abstract
In this work, the reactions of carbamyl and thiocarbamyl halides with NH3 were studied in the gas phase at the MP2(FC)/6-31+G(d) level of theory. Single point calculations were performed at the QCISD/6-311+G(3df,2p) to refine the energetics. The reaction mechanisms were also studied in aqueous solution. The structures were fully optimized at the CPCM-MP2(FC)/6-31+G(d) and refined by a single point CPCM-QCISD/6- 311+G(3df,2p) calculations. The reaction mechanisms for the title compounds were compared with those for the acetyl and thioacetyl halides. The lower reactivity of carbamyl (and thiocarbamyl) groups was explained by comparing the C=O and C=S π-bond strengths as well as resonance contributions in the ground state.
Page
1955 - 1961
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