Journal of Organic Chemistry p. 1806 - 1810 (1984)
Update date:2022-08-15
Topics: nucleophiles H NMR data Lanthanide shift studies Kinetic and thermodynamic study 2,4,6-triphenylthiopyrylium ion Butylamine and cyclohexylamine Dimethyl sulfoxide Equilibration Proton transfer Pyrylium salts Organic cations Data Analysis Reaction Mechanism Conclusion Discussion Data Collection Kinetic Analysis Enthalpy (?H) Entropy (?S) Gibbs Free Energy (?G) Report
Doddi, Giancarlo
Ercolani, Gianfranco
A kinetic and thermodynamic study of the reaction of the 2,4,6-triphenylthiopyrylium ion (1) with butylamine and cyclohexylamine has been performed in (CH3)2SO at 25 deg C.The reaction involves the initial formation of both the corresponding 2H- and 4H-thiopyrans, which equilibrate to form only the more stable 2H adduct.The kinetic date are consistent with a two-step process wherein the formation of the protonated 2H- and 4H-thiopyran intermediates is the rate-controlling step.A comparison with the addition reaction of 1 with CH3O- shows that the relative stabilities of the 2H and 4H isomers are strongly affected by the charge of the thiopyran derivative.Equilibrium date indicate that the acidity of the ammonium ion is strongly enhanced by the presence of the thiopyranyl moiety.
View Morewebsite:http://www.hybio.com.cn
Contact:+86 755 26588093
Address:No.9 Linkong West Street, Hengdian Street, Huangpi District, Wuhan City, China.
Linyi Shengxin Pharmaceutical R&D Co., Ltd
Contact:+86-18653953873
Address:West First of Yufeng Road, Yishui County
Lishui Nanming Chemical Co., Ltd
Contact:+86-0578-2134101,2697830
Address:No.19 Tongji Road Shuige Industrial zone
Weifang Yukai Chemical Co.,Ltd.
website:http://www.yukaichem.com/en.html
Contact:+86-536-8865336
Address:binhai economic development zone,262737 shangdong,china
Shanghai Biobond Pharmaceutical Co.,Ltd
website:http://www.sh-biobond.com/EnglishIndex.aspx
Contact:021-68719686 /18939786273/ 18917373795
Address:Shanghai Zhangjiang
Doi:10.1248/cpb.54.476
(2006)Doi:10.1081/SCC-100104820
(2001)Doi:10.1021/jm00391a023
(1987)Doi:10.1002/jsfa.2740121105
(1961)Doi:10.1139/v59-119
(1959)Doi:10.1002/anie.201805258
()