Comparative Studies on the Reactions of Carbamyl and Thiocarbamyl Halides with NH3 in the Gas Phase and in Aqueous Solution: A Theoretical Study

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 solut...

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Published inBulletin of the Korean Chemical Society pp. 1955 - 1961
Main Authors 김창곤, In Suk Han, 손창국, Yu Hee Yu, Zhishan Su, 김찬경
Format Journal Article
LanguageEnglish
Published 대한화학회 20.06.2012
Subjects
화학
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ISSN0253-2964
1229-5949
DOI10.5012/bkcs.2012.33.6.1955

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Summary: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. KCI Citation Count: 4
Bibliography:http://journal.kcsnet.or.kr/main/j_search/j_abstract_view.htm?code=B120629&qpage=j_search&spage=b_bkcs&dpage=ar
G704-000067.2012.33.6.043
ISSN:0253-2964
1229-5949
DOI:10.5012/bkcs.2012.33.6.1955