The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ultraviolet spectra of 2-substituted furans and 5-substituted methyl furoates》. Authors are Manly, Donald G.; Amstutz, E. D..The article about the compound:Methyl 5-chlorofuran-2-carboxylatecas:58235-81-7,SMILESS:O=C(C1=CC=C(Cl)O1)OC).Reference of Methyl 5-chlorofuran-2-carboxylate. Through the article, more information about this compound (cas:58235-81-7) is conveyed.
Ultraviolet spectral data for simple furan compounds are reported. 2-Substituted furans were prepared by the methods of Manly and Amstutz (C.A. 51, 3549f). Passing Cl through rapidly stirred Me 2-furoate 3 hrs. at 150° gave 42% 5-Cl derivative, m. 40-1°, and 5-methoxy-2-furoates were prepared as previously reported (loc. cit.). 5-Phenylthio-2-furoic acid (loc. cit.) with CH2N2 gave 98% Me ester (I), b0.5 146-8° m. 39-40°. I with excess 30% H2O2 in AcOH gave a quant. yield of Ph 5-carbomethoxy-2-furyl sulfone, needles, m. 102-3°. Me 5-nitro-2-furoate, m. 79-80°, was prepared by the method of Freure and Johnson (C.A. 25, 1825). Carbonation of 4-PhOC6H4MgBr gave the acid, m. 158-9°; Me ester, m. 56-7° (95% EtOH), λmaximum 258.0 mμ (log ε 4.26). Addition of 4-HO2CC6H4N2Cl to PhSH in cold dilute NaOH gave a poor yield of 4-PhSC6H4CO2H, m. 170-4° (95% EtOH); Me ester (II), m. 69-70°, λmaximum 293.2 mμ (log ε 4.23). II with H2O2 yielded 4-PhSO2C6H4CO2Me, m. 145-6° (95% EtOH), λ 242.5 mμ (log ε 4.29). Other compounds reported (m.p. or b.p., λmaximum (mμ), and log ε given): BzOMe, b15 85°, 220.8, 4.08; 4-BrC6H4CO2Me, m. 77-8°, 245.0, 4.26; 4-MeOC6H4CO2Me, m. 47-8°, 256.5, 4.43; 4-O2NC6H4CO2Me, m. 95-6°, 259.0, 4.12; 1,4-C6H4(CO2Me)2, m. 139-40°, 242.5 4.47; Ph2SO2, m. 128-30°, 236.3 4.17; Ph2S, b15 151-3°, 231.8, 3.80; Ph2O, b12 129.5°, 226.7, 4.01. The following ultraviolet spectral data are reported for the 2-substituted furans [2-substituent, λmaximum (mμ), log ε, Δ λ(λmaximum – λ where λ = 208), ΔλPh (λmaximum – λ where λ = 203.5 given]: H, 208 (by extrapolation), 3.9, 0, 0; Br, 215.5, 3.99, 7.5, 6.5; MeO, 221.0, 3.82, 13.0, 13.5; PhO, 222.0, 4.06, 14.0, 23.2; PhS, 241.5, 4.21, 33.5, 28.3; PhSO2, 249.5, 4.13, 41.5, 32.8; MeO2C, 252.1, 4.13, 44.1, 26.3. The following ultraviolet spectral data are reported for the Me 5-substituted-2-furoates (5-substituent given): H, 252.1, 4.13, 44.1, 26.3; Cl, 260.5, 4.23, 52.5, 37.5; PhSO2, 261.7, 4.33, 53.7, 39.0; Br, 264.1, 4.23, 56.1, 41.5; MeO2C, 264.6, 4.19, 56.6, 38.5; PhO, 275.0, 4.25, 67.0, 54.5; MeO, 279.0, 4.10, 71.5, 53.0; PhS, 291.8, 4.33, 83.8, 89.7; O2N, 295.4, 4.08, 87.4, 55.0.
In some applications, this compound(58235-81-7)Reference of Methyl 5-chlorofuran-2-carboxylate is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem