01407nas a2200169   4500008004100000245008500041210006900126260000800195300001000203490000800213520082300221100001801044700002101062700002301083700001701106856011401123       2017                        eng d00aMechanistic study of nucleophilic fluorination promoted by tri-tert-butanolamine0 aMechanistic study of nucleophilic fluorination promoted by trite  cMAY  a80-860 v1973 aQuantum chemical study is carried out to elucidate the mechanism of S(N)2 fluorination using. CsF promoted by tri-tert-butanolamines. Focus is on the role of the hydroxyl (OH) and the amine functional groups for accelerating the reaction. Our systematic analysis indicates that the OH groups form strong interactions with the nucleophile F-. Thus, it seems that hydrogen bonding with the nucleophile may accelerate the S(N)2 processes rather than retard them, as conventional wisdom suggests. The origin of the experimentally observed improvement of the promotor efficiency in t-butanol solvent over that in CH3CN is examined. We show that the coordination of the solvent t-butanol molecule as Lewis base on the counter-cation Cs+ lowers the Gibbs free energy of activation. (C) 2017 Elsevier B.V. All rights reserved.1 aLee, Sung-Sik1 aJung, Hyun-Kyung1 aShinde, Sandip, S.1 aLee, Sungyul  uhttps://library.ncl.res.in/content/mechanistic-study-nucleophilic-fluorination-promoted-tri-tert-butanolamine