The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation and properties of some bipyrazolyls》. Authors are Finar, I. L..The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).Product Details of 13599-22-9. Through the article, more information about this compound (cas:13599-22-9) is conveyed.
The synthesis of 5,5′-dimethyl-1,1′-diphenyl-(I) and 1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (II) was repeated, and the 3,5′-isomer (III) of the latter was isolated. Evidence was given for the orientations of these two isomers, and some 4,4′-disubstituted derivatives of I, II, and III were prepared (CO2Et)2 (IV) (36.5 g.) and 29 g. dry Me2CO were added during 25 min. to NaOMe (from 12.5 g. Na) under Et2O at 0°, the mixture was stirred for 2 days to give 21-38% octane-2,4,5,7-tetraone (V), yellow needles, m. 120-1° (from MeOH). IV (36.5 g.) and 1/2 of 16 g. PhCOMe were similarly treated, the other 1/2 added 4 hrs. later, and the mixture stirred 3 days to give 62-74% 1,6-diphenylhexane-1,3,4,6-tetraone (VI), yellow needles, m. 177-9°. V (3.4 g.) was heated with 4.3 g. PhNHNH2 in HOAc for 1 hr. to give 3.4 g. I, buff needles, m. 141-2°. VI (47.2 g.) was similarly treated 3-4 hrs. with 34.6 g. PhNHNH2 to give 35.2 g. II, m. 233°. The filtrate was diluted with H2O and then crystallized to yield 12.2 g. III, white needles, m. 135-6°. VI (58.8 g.) in HOAc was treated during 2.75 hrs. with 21.6 g. PhNHNH2 in HOAc, heated for a further 1.25 hrs., and set aside for 2 days to give after fractional crystallization unchanged starting material, II, and 3-(α-benzoylacetyl)-1,5-diphenylpyrazole (VII), yellow needles, m. 164-6.5°. VII on oxidation with alk. KMnO4 yielded 1,5-diphenylpyrazole-3-carboxylic acid (VIII), m. 185-6°. VII (2.9 g.) and 0.97 g. PhNHNH2 in HOAc heated 1 hr., and kept at room temperature overnight gave 2.4 g. II and 1 g. III. The infrared spectra of II and III were complex and similar. In general, the lowering of the symmetry as in III increases the number of bands. III in the 1600-650 cm.-1 region had 25 strong bands. Bischler’s method [Ber. 25, 3143(1892)] of preparing VIII was modified as follows: MeCOCH2CO2Et (30 g.) was refluxed 6 hrs. with 5.4 g. Na wire under Et2O, then 46 g. BzCH2Br in Et2O was added to maintain gentle reflux, then refluxed 2 hrs., and set aside overnight to give 56 g. AcCH(CH2Bz)CO2Et (IX) as a red oil. IX (12.4 g.) in EtOH was treated in the cold with 4.65 g. PhN2Cl, and then 16.4 g. NaOAc in H2O, the mixture set aside 24 hrs. in ice, and the oil which separated heated 15 min. with 6 g. NaOH in a little H2O to give 6.7 g. VIII. I in CHCl3 was treated with Br at room temperature to yield 4,4′-dibromo-5,5′-dimethyl-1,1′-diphenyl-3,3′-bipyrazolyl, rods, m. 159-60°. 4,4′-Dibromo-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl, plates, m. 272-3°. 4,4′-Dibromo-1,1′,3′,5-tetraphenyl-3,5′-bipyrazolyl, white rosettes, m. 200-1°. II (13.2 g.) in HOAc and 26 cc. concentrated HCl was heated 2 hrs. with 2.4 g. paraformaldehyde to give the 4,4′-bis(chloromethyl) derivative, white needles, (6.2 g.), m. 274-6°. I (3.14 g.) in HOAc was heated 0.5 hrs. with 6.37 g. HgAc2 to yield 4.8 g. 4,4′-bis(acetoxymercuri) compound (X), white needles, m. 204-4.5° (aqueous HOAc). II (4.38 g.) similarly treated yielded after 5 hrs. refluxing 7.6 g. 4,4′-bis(acetoxymercuri)-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (XI), white powder, m. 271.5°. The mercuri compounds when treated with HOAc and Br at room temperature gave the corresponding 4,4′-di-Br compounds X refluxed with dilute HCl gave I; however, XI had to be refluxed for some time with HOAc containing concentrated HCl before II could be obtained.
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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem