Electronic Supplementary Material

Gated Decoupling 13C NMR Application to Determine Conformation and Non Questionable Chemical Shift of Arylidene Barbiturates

José Daniel Figueroa-Villar

Medicinal Chemistry Group, Department of Chemistry, Military Institute of Engineering, Rio de Janeiro, RJ, Brazil

Fig. 1a 1H NMR Spectrum of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

Fig. 2a 13C NMR Spectrum of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

Fig. 3a gHSQC Spectrum of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

Fig. 4a gHMBC Spectrum of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

Table 1a NMR data of 1H, gHSQC, gHMBC and NOESY-1D of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

dH (Int; m; J(Hz)) / gHSQC / gHMBC* / NOESY-1D
11.48 (1H,s) / - / 162.43, 122.32 / -
11.28 (1H,s) / - / 160.89, 122.32 / -
8.21 (1H,s) / 148.31 / 162.43, 160.89, 134.09, 133.10, 122.32 / 7.76 (w)
7.76 (1H,d,8.5) / 133.10 / 148.31, 135.52, 134.09, 128.42, 126.62 / 8.21(w), 7.47(s)
7.73 (1H,d,1.6) / 128.42 / 135.52, 134.09, 131.39, 126.62 / 7.47(w)
7.47 (1H,dd,1.6,8.5) / 126.62 / 135.52, 134.09, 131.39, 128.42 / 7.76(s), 7.73(w)

Table 2a 13C NMR of 5-(2,4-dichlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione (3a)

dC / APT / GATED 13C
Mult. / J (Hz)
162.43 / C / d / 7.2
160.89 / C / d / 11.0
150,14 / C / s / -
148.31 / CH / dd / 4.0 and 161.1
135.52 / C / dt / 3.5 and 12.8
134.09 / C / dtd / 1.7, 4.1 and 11.3
133.10 / CH / dd / 4.6 and 169.4
131.39 / C / dd / 5.5 and 8.3
128.42 / CH / dd / 5.3 and 172.8
126.62 / CH / dd / 5.3 and 170.0
122.32 / C / q / 4.1

Fig. 5a 1H NMR Spectrum of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

Fig. 6a 13C NMR Spectrum of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

Fig. 7a gHSQC NMR Spectrum of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

Fig. 8a gHMBC NMR Spectrum of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

Fig. 9a Chemical shift assignment of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

Table 3a NMR data of 1H, gHSQC, gHMBC and NOESY-1D of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

dH / gHSQC / gHMBC / NOESY-1D
13.20 (1H,s) / - / - / 8.08 (s)
11.39 (1H,s) / - / - / -
11.31 (1H,s) / - / - / -
8.12 (1H,s) / 136.34 / 164.64, 163.69, 156.60, 123.55, 107.59 / 2.44(s)
8.08 (1H,s) / 142.21 / 156.60, 123.55 / 13.20 (s)
2.44 (3H,s) / 13.37 / 156.60, 123.55 / 8.12 (s)

w: weak and s: strong

Table 4a 13C NMR data of 5-[(4-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3b)

dC / APT / GATED 13C
Mult. / J (Hz)
164.64 / C / d / 10.4
163.60 / C / d / 6.8
156.60 / C / m / -
149.96 / C / s / -
142.21 / CH / dd / 4.7 and 210.8
136.35 / CH / d / 152.8
123.55 / C / m / -
107.59 / C / m / -
13.37 / CH3 / q / 127.8

Fig. 10a 1H NMR Spectrum of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

Fig. 11a 13C NMR spectrum of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

Fig. 12a gHSQC spectrum of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

Fig. 13a gHMBC spectrum of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

Fig. 14a Chemical shift assignment of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

Table 5a NMR data of 1H, gHSQC, gHMBC and NOESY-1D of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

dH / gHSQC / gHMBC / NOESY-1D
11.05 (1H,s) / - / - / -
10.95 (1H,s) / - / - / -
8.91 (1H,s) / 144.31 / 145.27 / 8.12 (w)
8.13 (1H,bs) / 145.26 / 144.31, 127.57 / 3.82
8.12 (1H,s) / 135.23 / 163.35, 161.87, 144.36, 127.57, 111.56 / 8.81 (w), 3.82 (s)
3.82 (3H,s) / 31.37 / 145.26, 127.57 / 8.13, 8.12 (s)

w: weak and s: strong

Table 6a 13C NMR data of 5-[(1-methyl-1H-imidazol-5-yl)methylene]pyrimidine-2,4,6-(1H,3H,5H)-trione (3c)

dC / APT / GATED 13C
Mult. / J (Hz)
163.35 / C / d / 6.9
161.87 / C / d / 10.4
149.68 / C / s / -
145.26 / CH / ddq / 206.8, 12.7 e 3.8
144.31 / CH / ddd / 198.6, 10.0, 6.9
135.23 / CH / d / 150.3
127.56 / C / m / -
111.56 / C / m / -
31.37 / CH3 / q / 141.9

Fig. 15a Expanded gHMBC of 3a indicating the difference between the interaction of H7 with carbons 162.43 and 160.89 ppm.