Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

N,N-dialkyl perfluoroalkanesulfonamides: Synthesis, characterization and properties

“…The structures and chemical compositions of these compounds were confirmed by NMR ( 1 H and 19 F) and elemental analysis (see Section 4.3). The characterization data in this work for the known compounds (1a, 1c, 3a, 3c and 5a-c) are in agreement well with those reported in literature [4,[7][8][9]13,[17][18][19].…”

“…Perfluoroalkanesulfonamides, such as N-alkyl perfluorooctanesulfonamides and N,N-dialkyl perfluorooctanesulfonamides, have been widely used in pesticides, surfactants, surface treatments for clothes and home furnishings, paper protections and other biological applications [1][2][3][4][5][6][7]. This kind of compounds is suitable for these industrial and biological purposes mainly because of their unique properties, which result from the high electronegativity of fluorine, its large van der Waals radius compared to hydrogen and the strong fluorine-carbon bond [4].…”

The Effect of Various Zinc Binding Groups on Inhibition of Histone Deacetylases 1–11

“…4-Phenylbutanohydroxamic acid (7) and valprohydroxamic acid (13) were synthesized from the corresponding carboxylic acids via esterification with methanol and subsequent reaction with hydroxylamine, as previously described. [30] N-(2-phenethyl)trifluoromethanesulfonamide (11), [31] N-(2phenethyl)methanesulfonamide (12), [32] N,N-dipropyltrifluoromethanesulfonamide (14), [33] and N,N-dipropylmethanesulfonamide (15) [34] were synthesized by sulfonylation of the corresponding amines. Similarly, sulfonylation of 6-amino-N-phenylhexanamide hydrochloride (24) [35] afforded N-phenyl-6-(trifluoromethylsulfonylamino)hexanamide (21) and 6-methylsulfonamino-N-phenylhexanamide (22), [36] whereas DIC/HOBt mediated coupling with crotonic acid afforded 6-trans-crotonylamino-N-phenylhexanamide (23) (Scheme 1).…”

“…N-(2-Phenethyl)methanesulfonamide (12): [32] N,N-Dipropyltrifluoromethanesulfonamide (14): [33] General sulfonamide formation procedure from N,N-dipropylamine. Yield 94 %; R f = 0.5 (EtOAc/heptane 10:90 (v/v)).…”

“…Analytical data are in agreement with those previously reported.N,N-Dipropyltrifluoromethanesulfonamide (14):[33] General sulfonamide formation procedure from N,N-dipropylamine. Analytical data are in agreement with those previously reported.N,N-Dipropyltrifluoromethanesulfonamide (14):[33] General sulfonamide formation procedure from N,N-dipropylamine.…”