The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Luminescence phenomena in pyrazoline derivatives》. Authors are Straus, Fritz; Muffat, Carl; Heitz, W..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).SDS of cas: 13599-22-9. Through the article, more information about this compound (cas:13599-22-9) is conveyed.
cf. Auwers and Voss, C. A. 4, 586. The reaction whereby 1-phenylpyrazolines are obtained by the action of PhNHNH2 on certain aromatic ketones, owing to the extraordinary ease with which the hydrazones first formed rearrange, has been extended to a number of substituted ketones and hydrazines. PhCH:CHCOCH:CHPh reacts in this way, so that adopting Auwers’ scheme of classification, PhCH: CHCOR’, the grouping PhCH:CH falls in with aromatic and sec. or tert. aliphatic residues in favoring ring closure. The α- and β-naphthylhydrazones form the pyrazolines as easily as the Ph compounds NO2 groups in the p-position in the hydrazine residue and o- but not p-MeO groups in the ketone Ph residues make the ring closure more difficult. Halogens do not markedly hinder the pyrazoline formation as long as they are present only in the ketone or the hydrazine residue, but if present in both they render the hydrazones quite stable. These pyrazoline compounds show vivid fluorescence under the influence of Röntgen rays, almost as intense as that of BaPt(CN)4 in some cases, and not only in the solid state but in solution also, depending to a marked degree on the nature of the solvent; the alc. and AcOH solutions become only faintly luminescent while in CS2, C6H6 and CHCl3 the phenomenon is surprizingly intense. The compounds also show vivid fluorescence in diffuse daylight. The fluorescence produced in these 1,3,5-substituted pyrazolines by Röntgen rays differs from that produced by daylight, however, in that it is limited to those compounds in which an unsaturated residue (Ph or CO) is substituted in positions 3 and 5; where the limit for the daylight fluorescence lies has not been determined with certainty but as fluorescence of simple pyrazolines is nowhere mentioned, it is probably produced by a Ph group in position 1. The hydrazones first formed, which have been isolated in some cases, are intensely colored, even more so than their isomeric pyrazolines, but show no fluorescence. The pyrazoline ring, however, is not in itself the seat of the fluorescence phenomenon; the cyclic compounds resulting from the phenylhydrazones of cinnamylideneacetophenone and dicinnamylideneacetone, which do not contain a pyrazoline ring, also fluoresce under the influence of Röntgen rays. The intensity of the fluorescence depends on the nature of the substituents, increasing in the order below with the following substituents in positions 1, 3 and 5, resp.: Ph, Ph, Ph; Ph, p-Me2NC6H4CH:CH, p-Me2NC6H4; Ph, PhCH: CH, Ph; Ph, p-ClC6H4, p-ClC6H4; Ph, p-MeOC6H4CH:CH, p-MeOC6H4; Ph, p-ClC6H4CH:CH, p-ClC6H4; p-BrC6H4, p-ClC6H4CH:CH, p-ClC6H4. O2NC6H4 in position 1 destroys the fluorescence under the rays but not in daylight; 1-α- and β-C10H7 derivatives fluoresce. This fluorescence under Röntgen rays is not limited to these pyrazolines, however; it is found, partly in conjunction with ordinary fluorescence, in Ph-substituted ethylenes, butadienes and hexatrienes; the Ph-substituted acetylenes show it faintly; Ph3CH very brightly; CPh4 not at all; anthracene and retene very faintly; ms-dibromoanthracene intensely; hydrocollidinedicarboxylic ester quite strongly. The constitutions of the following hydrazones and pyrazolines were determined by the methods of A. and V. 1,5-Diphenyl-3-styrylpyrazoline, PhN.N:C(CH:CHPh).CH2.CHPh, m. 147-8° (Minunni, Gazz. chim. ital. 29, II, 398(1899)), evaporated to dryness with 2% KMnO4, gave BzOH and 1,5-diphenylpyrazole-3-carboxylic acid, needles from H2O, m. 183°; the pyrazoline is unchanged by Na-Hg and by boiling with AcOH; it dissolves in H2SO4 with golden yellow color and gives with FeCl3 a green color changing to blue. 1-α-Naphthyl-3-styryl-5-phenylpyrazoline, obtained by filtering a hot solution of 5 g. α-C10H7NHNH2.HCl and 2.7 g. KOAc in 200 g. absolute alc. from the precipitated KCl, boiling 1 hr. with 5 g. (PhCH:- CH)2CO in 100 cc. alc., then 0.5 hr. longer with charcoal, filtering, concentrating in vacuo to 0.5 its volume, pouring off the alc. after cooling and drying in vacuo over H2SO4, yellow needles with green fluorescence from absolute alc. containing some AcOEt, m. 164°. β-Isomer, yellow, felted needles with faint green fluorescence from AcOEt, m. 195°. 1-p-Bromophenyl-3-styryl-5-phenylpyrazoline, from 4 g. (PhCH:CH)2CO allowed to stand 2 days with 5 g. p-BrC6H4NHNH2 in 20 cc. AcOH, yellow needles with green fluorescence from AcOEt, m. 177°, soluble in H2SO4 with dirty green color changing to deep green on addition of FeCl3, unchanged by Na-Hg or boiling AcOH. From 4.5 g. (PhCH:CH)2CO boiled 3 hrs. with 3 g. p-O2NC6H4NHNH2 in alc. and a little AcOH and allowed to stand several days is obtained dibenzalacetone p-nitrophenylhydrazone, yellow-red leaflets from C6H6, m. 173°, soluble in H2SO4 with red-yellow color; 1.7 g. in 20 cc. AcOEt and 10 cc. AcOH reduced with 60 g. Na-Hg gave 0.5 g. crude solid p-C6H4(NH2)2, while boiling 1 hr. in 20 parts AcOH converts it into 1-p-nitrophenyl-3-styryl-5-phenylpyrazoline, yellow-red crystals with intense green fluorescence from AcOEt, m. 204-5°, soluble in H2SO4 with red-violet color hardly changed by FeCl3. o,o’-Dimethoxydibenzalacetone phenyl-hydrazone, brown-yellow warts from alc., m. 142°, reduced by Na-Hg in EtOH-AcOH to PhNH2 and rearranged by boiling AcOH into 1-phenyl-3-0-methoxystyryl-5-0-methoxyphenylpyrazoline, light yellow crystals from alc. (in which they form a solution with green-blue fluorescence), m. 153-4.5°, soluble in H2SO4 with red-yellow color changed to blue by FeCl3, gives no PhNH2 with Na-Hg. 1-Phenyl-3-p-methoxystyryl-5-p-methoxyphenylpyrazoline, from 5 g. dianisalacetone and 5 g. PhNHNH2 boiled 2 hrs. in 50 cc. C6H6, white-yellow leaflets (appearing almost green from their intense fluorescence) from AcOEt, m. 159°; it is more easily obtained by boiling the ketone and hydrazine 5 min. in 10 parts AcOH. 1-Phenyl-3-p-dimethylaminostyryl-5-p-dimethyl-aminophenylpyrazoline, yellow needles with extraordinarily intense green fluorescence from AcOEt, m. 192°. o,o’-Dichlorodibenzalacetone, obtained in rather poor yield by boiling 5 g. o-ClC6H4CHO and 1 g. Me2CO in 60 cc. alc. 15 min. with 3 cc. of 5% NaOMe, yellow needles from MeOH, m. 125°; p-bromophenylhydrazone, dark yellow, crystals from MeOH, m. 145°. 1-Phenyl-3-0-chlorostyryl-5-0-chlorophenylpyrazoline, yellow needles from alc. (the solution shows green fluorescence), m. 145°, soluble in H2SO4 with yellow-green color turned dark by FeCl3, unchanged by boiling AcOH. 1-Phenyl-3-p-chlorostyryl-5-p-chlorophenylpyrazoline, fine, yellow needles with strong green fluorescence from AcOEt, m. 212°, gives no PhNH2 with Na-Hg, gives so faint a reaction with FeCl3 in H2SO4 as not to reveal the presence of a pyrazoline. p,p-Dichlorodibenzalacetone p-bromophenylhydrazone, from 5 g. of the ketone and 3.5 g. of the hydrazine shaken 3 days, protected from the light, in 50 cc. AcOH yellow needles from C6H6, m. 183°, stable only in H, quickly turns brown in the air, soluble in H2SO4 with yellow color changed transiently green, then brown, by FeCl3, reduced by Na-Hg in EtOH-AcOH to p-BrC6H4NH2 and converted by boiling AcOH into 1-p-bromophenyl-3-p-chlorostyryl-5-p-chlorophenylpyrazoline, yellow needles with intense green fluorescence from alc., m. 173-4°, soluble in H2SO4 with yellow color changed to deep green by FeCl3, unchanged by Na-Hg. Methyl 1-phenyl-3-β-carbomethoxyvinylpyrazoline-5-carboxylate, PhN.N:C(CH:CHCO2Me).CH2.CHCO2Me, from CO(CH:CHCO2Me)2 and PhNHNH2 in boiling C6H6, yellow leaflets with green fluorescence from AcOEt, m. 153°, soluble in H2SO4 with red-yellow color changed to dark blue by FeCl3 (yield rather poor), unchanged by boiling AcOH. Ethyl ester, yellow leaflets with green fluorescence, m. 92.5°, hydrolyzed by aqueous alc. NaOH on the H2O bath to the free dicarboxylic acid, yellow needles, m. 204° (decomposition); Pb salt, yellow, finely granular precipitate Dimethyl ketopentadienedicarboxylate phenylmethylhydrazone, from the ester and the hydrazine in AcOH at 40°, dark red, refractive crystals from MeOH, m. 105°. Diethyl ester p-bromophenylhydrazone, deep red-yellow needles from MeOH, m. 134°. From 5 g. of A. and V.’s PhCH:CHCH: CHC(:NNHPh)Ph boiled 1 hr. with 20 cc. AcOH is obtained an isomer (a), probably PhN.N:CPh.CH:CH.CH2.CHPh or PhN.N:CPh.CH2.CH:CH.CHPh, warts with faint fluorescence from AcOH, m. 123-4°, soluble in H2SO4 with green-blue color changed to green by FeCl3, while the hydrazone dissolves with yellow color changed to brown by FeCl3; Na-Hg gives no PhNH2 but resinifies the substance. PhCH:CHCH: CHC(:NNHPh)Me dissolves in H2SO4 with red-yellow color changed to dirty green by FeCl3, yields PhNH2 with Na-Hg and is converted by boiling AcOH into an oil strongly fluorescing in C6H6 and whose red-yellow solution in H2SO4 is turned blue-red by FeCl3, while Na-Hg gives no PhNH2. (PhCH:CHCH:CH)2O and PhNHNH2 heated in AcOH and then in alc. give orange-yellow needles from alc. and AcOEt, m. 142° (Diel and Einhorn, Ber. 18, 2,325 (1885), describe a “”phenylhydrazone”” as m. 155°), dissolves in H2SO4 with orange-red color changing to blue on standing 10 sec. or adding FeCl3, gives no PhNH2 with Na-Hg but is resinified, is unchanged by AcOH. Evidently the substance is not a hydrazone but a cyclic compound analogous to (a) above. On oxidation with KMnO4 BzOH was the only product which could be isolated.
Here is a brief introduction to this compound(13599-22-9)SDS of cas: 13599-22-9, if you want to know about other compounds related to this compound(13599-22-9), you can read my other articles.
Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem