[Reactions of 1-(X-benzoyl)-4-R-thiosemicarbazide with chloroacetone and omega-bromoacetophenone. III. 4-Phenyl- and 4-(p-tolyl)- thiosemicarbazide of 0-nitrobenzoic acid].
Reactions of 4-phenyl- and 4-(p-tolyl)-thiosemicarbazide of o-nitrobenzoic acid (Ie-f) with chloroacetone and omega-bromoacetophenone were investigated in: 1) methanolic medium (method D); 2) methanolic medium in the presence of anhydrous CH3COONa (method E); 3) methanolic medium in the presence of N(C2H5)3 (method F.). The properties of compounds IIi-1 and IIIi-1 were determined under the conditions of basic and acidic hydrolysis. The results of UV and IR spectroscopic measurements as well as those of in vitro investigations were reported. The formation of the mixture of isomeric compounds II and III (Parts I-III) takes place also in the reaction of 4-R-thiosemicarbazides of acids stronger than benzoic (Ia-f) in methanol (method D). This may be clarified basing on the pKa value for the reaction: R1-CO-NH-NH2 + H+<-->R1CO-NH-NH3+ for the proper hydrazides (R1 = C6H5; p-Cl-C6H4; p-O2N-C6H4; o-O2N-C6H4).
Bielak
E
E
Katedra i Zakład Chemii Ogólnej, Akademia Medyczna w Lublinie.
Biliński
S
S
D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry; D000098:Acetophenones / Q000737:chemistry*; D006868:Hydrolysis; D009579:Nitrobenzoates / Q000737:chemistry*; D012663:Semicarbazides / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000098:Acetophenones; D009579:Nitrobenzoates; D012663:Semicarbazides; D000096:Acetone; C005151:thiosemicarbazide; C006973:chloroacetone; C013190:phenacyl bromide; C008629:4-nitrobenzoic acid
Reakcje 1-(X-benzoilo)-4-R-tiosemikarbazydu z chloroacetonem i omega-bromoacetofenonem. III. 4-Fenylo- i 4-(p-tolilo)-tiosemikarbazyd kwasu o-nitrobenzoesowego.