aaronqiu/science_chemistry huggingface dataset:
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H22N4O5S
Degree of Unsaturation (DoU): 10.0
Spectral Data:
- 13C NMR: δ 14.0 (1C, s), 24.3 (1C, s), 25.5 (2C, s), 42.0 (1C, s), 45.8 (2C, s), 47.3 (1C, s), 52.1 (1C, s), 113.4 (1C, s), 116.6 (1C, s), 142.2 (1C, s), 147.1 (1C, s), 154.7 (1C, s), 156.5 (1C, s), 160.1 (1C, s), 169.7 (1C, s), 170.5 (1C, s)
- 1H NMR: δ 1.39-1.67 (6H, 1.47 (dtt,  J  = 12.2, 6.6, 2.7 Hz), 1.58 (ddddd,  J  = 12.6, 6.8, 6.6, 2.8, 2.7 Hz)), 2.41 (3H, s), 3.36 (4H, ddd,  J  = 15.4, 6.8, 2.8 Hz), 3.64-3.80 (5H, 3.69 (s), 3.75 (s)), 4.75 (2H, s), 8.56 (1H, s). Determine the complete molecular structure.
Answer: COC(=O)CNC(=O)c1sc2ncn(CC(=O)N3CCCCC3)c(=O)c2c1C
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C17H19FN2O4
Degree of Unsaturation (DoU): 9.0
Spectral Data:
- 13C NMR: δ 13.8 (1C, s), 47.2 (1C, s), 53.2 (1C, s), 56.0 (1C, s), 67.0 (1C, s), 75.1 (1C, s), 107.9 (1C, s), 108.7 (1C, s), 111.8-111.9 (2C, 111.8 (s), 111.8 (s)), 116.0 (1C, s), 119.3 (1C, s), 148.4 (1C, s), 152.3 (1C, s), 156.3 (1C, s), 157.3 (1C, s), 161.8 (1C, s)
- 1H NMR: δ 2.26 (3H, s), 3.36-3.86 (9H, 3.44 (ddd,  J  = 14.4, 3.3, 2.4 Hz), 3.58 (ddd,  J  = 14.3, 3.2, 2.4 Hz), 3.61 (dd,  J  = 13.9, 3.3 Hz), 3.66 (dd,  J  = 13.9, 10.2 Hz), 3.67 (ddd,  J  = 14.4, 10.2, 3.2 Hz), 3.73 (ddd,  J  = 14.3, 10.2, 3.3 Hz), 3.81 (s)), 4.54 (1H, dd,  J  = 10.2, 3.3 Hz), 6.02-6.20 (2H, 6.08 (d,  J  = 3.5 Hz), 6.15 (d,  J  = 3.5 Hz)), 6.71 (1H, dd,  J  = 8.6, 0.5 Hz), 7.07 (1H, dd,  J  = 8.6, 1.8 Hz), 7.67 (1H, dd,  J  = 1.8, 0.5 Hz). Determine the complete molecular structure.
Answer: COc1ccc(F)cc1NC(=O)N1CCO[C@H](c2ccc(C)o2)C1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H15BrN2O4S
Degree of Unsaturation (DoU): 12.0
Spectral Data:
- 13C NMR: δ 35.5 (1C, s), 55.9 (1C, s), 56.0 (1C, s), 111.8 (1C, s), 114.8 (1C, s), 127.7 (1C, s), 128.0 (1C, s), 128.7 (1C, s), 129.8 (2C, s), 130.0 (1C, s), 132.0 (2C, s), 148.5 (1C, s), 148.7 (1C, s), 163.0 (1C, s), 164.2 (1C, s), 193.5 (1C, s)
- 1H NMR: δ 3.74-3.97 (8H, 3.79 (s), 3.88 (s), 3.92 (s)), 7.05 (1H, dd,  J  = 8.6, 0.5 Hz), 7.39 (1H, dd,  J  = 1.6, 0.5 Hz), 7.51-7.72 (3H, 7.58 (dd,  J  = 8.6, 1.6 Hz), 7.66 (ddd,  J  = 8.7, 1.3, 0.5 Hz)), 7.93 (2H, ddd,  J  = 8.7, 1.8, 0.5 Hz). Determine the complete molecular structure.
Answer: COc1ccc(-c2nnc(SCC(=O)c3ccc(Br)cc3)o2)cc1OC
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H23BrClNO6
Degree of Unsaturation (DoU): 7.0
Spectral Data:
- 13C NMR: δ 22.0 (1C, s), 22.2 (1C, s), 29.1-29.3 (2C, 29.2 (s), 29.2 (s)), 63.3 (1C, s), 75.0 (1C, s), 76.0-76.0 (2C, 76.0 (s), 76.0 (s)), 77.4 (1C, s), 111.3 (1C, s), 112.8 (1C, s), 117.2 (1C, s), 121.6 (1C, s), 122.9 (1C, s), 130.9 (1C, s), 135.3 (1C, s), 139.3 (1C, s), 150.5 (1C, s)
- 1H NMR: δ 0.99-1.11 (9H, 1.04 (s), 1.04 (s), 1.06 (s)), 1.34 (3H, s), 3.48 (1H, t,  J  = 6.7 Hz), 3.87-3.99 (2H, 3.93 (d,  J  = 6.7 Hz), 3.93 (d,  J  = 6.7 Hz)), 7.09-7.29 (2H, 7.14 (d,  J  = 0.5 Hz), 7.23 (d,  J  = 8.0 Hz)), 7.44 (1H, dd,  J  = 8.0, 0.5 Hz). Determine the complete molecular structure.
Answer: C[C@]1(Oc2c[nH]c3ccc(Br)c(Cl)c23)O[C@H](CO)[C@@](C)(O)[C@](C)(O)[C@@]1(C)O
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C23H26N4O2
Degree of Unsaturation (DoU): 13.0
Spectral Data:
- 13C NMR: δ 23.5 (1C, s), 24.2 (1C, s), 27.7 (1C, s), 33.2 (1C, s), 34.6 (1C, s), 36.6 (1C, s), 42.8 (1C, s), 45.8 (1C, s), 53.2 (1C, s), 123.8 (1C, s), 126.7 (1C, s), 127.2 (1C, s), 128.7 (2C, s), 129.0 (2C, s), 130.0 (1C, s), 139.5 (1C, s), 148.7 (1C, s), 151.5 (1C, s), 167.0 (1C, s), 169.7 (1C, s), 179.2 (1C, s)
- 1H NMR: δ 1.42-1.68 (4H, 1.49 (ddt,  J  = 12.7, 2.9, 2.6 Hz), 1.53 (ddddd,  J  = 12.2, 3.3, 2.9, 2.7, 2.3 Hz), 1.56 (dtd,  J  = 12.7, 10.3, 2.7 Hz), 1.59 (dtdd,  J  = 12.2, 10.2, 3.4, 2.6 Hz)), 1.92-2.04 (2H, 1.98 (quint,  J  = 7.4 Hz), 1.98 (quint,  J  = 7.4 Hz)), 2.07-2.25 (3H, 2.15 (ttdd,  J  = 10.2, 4.7, 3.4, 2.6 Hz), 2.19 (t,  J  = 7.4 Hz), 2.19 (t,  J  = 7.4 Hz)), 2.34-2.46 (2H, 2.40 (d,  J  = 4.7 Hz), 2.40 (d,  J  = 4.7 Hz)), 2.89-3.01 (2H, 2.95 (t,  J  = 7.4 Hz), 2.95 (t,  J  = 7.4 Hz)), 3.20-3.53 (4H, 3.27 (ddd,  J  = 15.4, 3.4, 2.3 Hz), 3.34 (ddd,  J  = 15.4, 10.2, 3.3 Hz), 3.41 (dd,  J  = 14.9, 3.4 Hz), 3.45 (dd,  J  = 14.9, 10.2 Hz)), 7.11-7.33 (5H, 7.17 (dddd,  J  = 7.8, 1.3, 1.1, 0.5 Hz), 7.20 (tt,  J  = 7.7, 1.3 Hz), 7.27 (tdd,  J  = 7.8, 1.8, 0.5 Hz)), 7.46 (1H, ddd,  J  = 7.6, 4.7, 0.5 Hz), 8.05 (1H, ddd,  J  = 7.6, 1.9, 1.6 Hz), 8.60 (1H, dt,  J  = 4.7, 1.9 Hz), 9.12 (1H, ddd,  J  = 1.9, 1.6, 0.5 Hz). Determine the complete molecular structure.
Answer: O=C(CCCc1nc(-c2cccnc2)no1)N1CCC[C@@H](Cc2ccccc2)C1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C20H17FN4O2
Degree of Unsaturation (DoU): 14.0
Spectral Data:
- 13C NMR: δ 35.3 (1C, s), 40.5 (1C, s), 73.2 (1C, s), 113.2 (1C, s), 114.5 (1C, s), 119.1 (1C, s), 123.2 (1C, s), 126.9 (2C, s), 127.8 (1C, s), 128.5 (2C, s), 130.5 (1C, s), 136.9 (1C, s), 138.3 (1C, s), 148.9 (1C, s), 153.9 (1C, s), 162.9 (1C, s), 166.0 (1C, s), 169.9 (1C, s)
- 1H NMR: δ 2.46-2.75 (2H, 2.54 (dd,  J  = 15.4, 9.6 Hz), 2.68 (dd,  J  = 15.4, 4.5 Hz)), 3.56 (3H, s), 4.01 (1H, dd,  J  = 9.6, 4.5 Hz), 7.07-7.33 (6H, 7.13 (ddd,  J  = 8.2, 1.4, 1.2 Hz), 7.19 (tt,  J  = 7.7, 1.3 Hz), 7.26 (dddd,  J  = 7.8, 7.7, 1.9, 0.5 Hz), 7.26 (dtd,  J  = 7.8, 1.3, 0.5 Hz)), 7.44-7.58 (2H, 7.51 (ddd,  J  = 8.4, 8.2, 0.4 Hz), 7.50 (ddd,  J  = 1.9, 1.4, 0.4 Hz)), 7.94 (1H, ddd,  J  = 8.4, 1.9, 1.2 Hz). Determine the complete molecular structure.
Answer: Cn1nc(NC(=O)c2cccc(F)c2)c2c1NC(=O)C[C@@H]2c1ccccc1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C24H25N3O2S
Degree of Unsaturation (DoU): 14.0
Spectral Data:
- 13C NMR: δ 37.8 (1C, s), 42.0 (1C, s), 44.6 (1C, s), 53.4 (1C, s), 54.8 (1C, s), 85.9 (1C, s), 120.6 (2C, s), 121.1 (1C, s), 126.2 (2C, s), 127.5 (1C, s), 128.3 (1C, s), 128.6 (2C, s), 129.3 (1C, s), 129.6 (1C, s), 135.0 (1C, s), 135.6 (1C, s), 138.5 (1C, s), 148.7 (2C, s), 150.4 (1C, s), 169.1 (1C, s)
- 1H NMR: δ 2.69 (2H, t,  J  = 2.7 Hz), 2.77-2.94 (2H, 2.84 (dd,  J  = 11.8, 1.8 Hz), 2.86 (dd,  J  = 11.8, 10.0 Hz)), 3.49-3.80 (6H, 3.54 (t,  J  = 2.7 Hz), 3.54 (t,  J  = 2.7 Hz), 3.62 (d,  J  = 17.7 Hz), 3.70 (d,  J  = 17.7 Hz), 3.75 (s), 3.75 (s)), 5.04 (1H, dd,  J  = 10.0, 1.8 Hz), 6.82-7.00 (2H, 6.89 (ddd,  J  = 7.9, 7.5, 1.2 Hz), 6.94 (ddd,  J  = 8.3, 1.2, 0.5 Hz)), 7.08-7.52 (7H, 7.14 (ddd,  J  = 5.0, 1.7, 0.5 Hz), 7.23 (ddd,  J  = 8.3, 7.5, 1.3 Hz), 7.28 (ddd,  J  = 7.9, 1.3, 0.5 Hz), 7.34 (tt,  J  = 7.7, 1.3 Hz), 7.45 (dddd,  J  = 8.0, 7.7, 1.6, 0.6 Hz)), 7.76 (2H, dddd,  J  = 8.0, 1.3, 0.9, 0.6 Hz), 8.56 (2H, ddd,  J  = 5.0, 1.9, 0.5 Hz). Determine the complete molecular structure.
Answer: O=C(CSc1ccncc1)NCCN1Cc2ccccc2O[C@@H](c2ccccc2)C1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H26N2O3
Degree of Unsaturation (DoU): 7.0
Spectral Data:
- 13C NMR: δ 19.4 (1C, s), 22.1 (1C, s), 28.9 (1C, s), 31.4 (1C, s), 33.8 (1C, s), 43.7 (1C, s), 50.0 (1C, s), 55.1 (1C, s), 66.8 (1C, s), 69.7 (1C, s), 72.2 (1C, s), 114.6 (2C, s), 122.0 (2C, s), 137.5 (1C, s), 157.3 (1C, s), 157.5 (1C, s)
- 1H NMR: δ 0.92 (3H, d,  J  = 6.8 Hz), 1.13 (3H, d,  J  = 6.7 Hz), 1.39-1.63 (5H, 1.47 (dtd,  J  = 12.7, 10.2, 3.4 Hz), 1.48 (dddd,  J  = 12.7, 3.3, 2.7, 2.3 Hz), 1.53 (ddd,  J  = 12.8, 3.4, 2.7 Hz), 1.54 (tqt,  J  = 10.3, 6.8, 2.7 Hz), 1.55 (dt,  J  = 12.8, 10.2 Hz)), 1.90 (1H, dddd,  J  = 14.5, 8.1, 6.9, 1.7 Hz), 2.20 (1H, dddd,  J  = 14.5, 7.7, 6.9, 4.2 Hz), 3.22-3.49 (3H, 3.30 (ddd,  J  = 14.1, 3.4, 2.3 Hz), 3.38 (ddd,  J  = 14.1, 10.2, 3.3 Hz), 3.42 (dqd,  J  = 10.2, 6.7, 3.4 Hz)), 3.81-4.05 (4H, 3.88 (ddd,  J  = 7.2, 6.9, 1.7 Hz), 3.90 (ddd,  J  = 7.7, 7.2, 6.9 Hz), 3.98 (dd,  J  = 6.8, 1.7 Hz), 3.99 (t,  J  = 6.8 Hz)), 4.72 (1H, dddd,  J  = 8.1, 6.9, 4.2, 1.7 Hz), 6.71 (2H, ddd,  J  = 8.8, 2.7, 0.5 Hz), 7.51 (2H, ddd,  J  = 8.8, 1.4, 0.5 Hz). Determine the complete molecular structure.
Answer: C[C@@H]1CCN(C(=O)Nc2ccc(O[C@@H]3CCOC3)cc2)[C@H](C)C1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C13H15NO3
Degree of Unsaturation (DoU): 7.0
Spectral Data:
- 13C NMR: δ -2.1 (1C, s)
- 1H NMR: δ 0.06 (4H, s). Determine the complete molecular structure.
Answer: C#CC(C)(C)NC(=O)c1ccc(OC)c(O)c1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H24N2O
Degree of Unsaturation (DoU): 8.0
Spectral Data:
- 13C NMR: δ 14.8 (1C, s), 21.1 (1C, s), 21.9 (1C, s), 31.1 (1C, s), 32.4 (1C, s), 32.9 (1C, s), 36.7 (1C, s), 39.3 (1C, s), 56.2 (1C, s), 108.8 (1C, s), 111.3 (1C, s), 118.6 (1C, s), 119.1 (1C, s), 122.0 (1C, s), 123.6 (1C, s), 127.1 (1C, s), 136.1 (1C, s), 169.1 (1C, s)
- 1H NMR: δ 0.84-1.04 (6H, 0.90 (d,  J  = 6.9 Hz), 0.98 (d,  J  = 7.0 Hz)), 1.22-1.68 (8H, 1.29 (dq,  J  = 11.3, 2.8 Hz), 1.32 (dtd,  J  = 11.3, 10.3, 2.8 Hz), 1.36 (tqd,  J  = 10.3, 6.9, 2.8 Hz), 1.47 (dquint,  J  = 12.9, 2.8 Hz), 1.54 (dtt,  J  = 12.9, 10.3, 2.8 Hz), 1.55 (ddt,  J  = 13.3, 10.3, 2.8 Hz), 1.57 (dqd,  J  = 10.3, 7.0, 2.8 Hz), 1.61 (dq,  J  = 13.3, 2.8 Hz)), 3.78-3.88 (2H, 3.83 (s), 3.83 (s)), 3.98 (1H, q,  J  = 2.8 Hz), 6.91-7.16 (2H, 6.98 (ddd,  J  = 8.0, 7.8, 1.2 Hz), 7.08 (ddd,  J  = 8.0, 7.8, 1.3 Hz)), 7.34 (1H, ddt,  J  = 8.0, 1.2, 0.5 Hz), 7.52 (1H, t,  J  = 0.5 Hz), 7.63 (1H, ddt,  J  = 8.0, 1.3, 0.5 Hz). Determine the complete molecular structure.
Answer: C[C@H]1[C@@H](NC(=O)Cc2c[nH]c3ccccc23)CCC[C@@H]1C
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H16F3N5O
Degree of Unsaturation (DoU): 12.0
Spectral Data:
- 13C NMR: δ 37.4 (1C, s), 43.6 (1C, s), 107.0 (1C, s), 119.7 (2C, s), 119.9 (1C, s), 123.4 (1C, s), 123.6 (1C, s), 126.7 (1C, s), 130.3 (1C, s), 133.6 (1C, s), 133.8 (1C, s), 140.3 (1C, s), 143.5 (1C, s), 149.0 (1C, s), 150.2 (2C, s), 155.3 (1C, s)
- 1H NMR: δ 3.83 (3H, s), 4.74 (2H, s), 6.79 (1H, s), 7.01-7.32 (3H, 7.08 (ddd,  J  = 7.7, 7.4, 1.4 Hz), 7.21 (ddd,  J  = 7.9, 7.4, 1.5 Hz), 7.26 (ddd,  J  = 7.9, 1.4, 0.5 Hz)), 7.52-7.74 (3H, 7.58 (ddd,  J  = 7.7, 1.5, 0.5 Hz), 7.68 (ddd,  J  = 4.9, 1.8, 0.4 Hz)), 8.59 (2H, ddd,  J  = 4.9, 1.8, 0.4 Hz). Determine the complete molecular structure.
Answer: Cn1nc(CNC(=O)Nc2ccccc2C(F)(F)F)cc1-c1ccncc1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C16H24N6O2S
Degree of Unsaturation (DoU): 8.0
Spectral Data:
- 13C NMR: δ 13.0 (1C, s), 13.5 (1C, s), 21.7 (1C, s), 24.4 (1C, s), 45.4 (2C, s), 49.1 (2C, s), 53.7 (1C, s), 110.4 (1C, s), 112.2-112.3 (2C, 112.2 (s), 112.2 (s)), 128.6 (1C, s), 150.4 (1C, s), 151.0 (1C, s), 157.4 (1C, s)
- 1H NMR: δ 0.87 (3H, t,  J  = 6.6 Hz), 1.32 (2H, tq,  J  = 7.0, 6.6 Hz), 1.91 (2H, tt,  J  = 7.0, 6.6 Hz), 2.24 (3H, s), 3.33-3.49 (6H, 3.41 (ddd,  J  = 15.3, 6.7, 2.8 Hz), 3.41 (t,  J  = 6.6 Hz)), 3.60 (4H, ddd,  J  = 14.4, 6.7, 2.8 Hz), 6.92 (1H, d,  J  = 7.3 Hz), 7.72 (1H, d,  J  = 8.9 Hz), 7.79-7.93 (2H, 7.85 (d,  J  = 8.9 Hz), 7.87 (d,  J  = 7.3 Hz)). Determine the complete molecular structure.
Answer: CCCCS(=O)(=O)N1CCN(c2ccc(-n3ccnc3C)nn2)CC1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C21H17FN2O3S
Degree of Unsaturation (DoU): 14.0
Spectral Data:
- 13C NMR: δ 25.7 (1C, s), 29.3 (1C, s), 61.3 (1C, s), 68.2 (1C, s), 77.6 (1C, s), 111.7 (1C, s), 112.6 (1C, s), 112.8 (1C, s), 120.6 (1C, s), 122.2 (1C, s), 123.3 (1C, s), 124.9 (1C, s), 125.2 (1C, s), 127.5 (1C, s), 130.8 (1C, s), 132.0 (1C, s), 148.1 (1C, s), 153.7 (1C, s), 155.4 (1C, s), 164.1 (1C, s), 169.1 (1C, s)
- 1H NMR: δ 1.74-2.14 (4H, 1.82 (dddd,  J  = 12.6, 7.1, 4.4, 2.0 Hz), 1.89 (dddd,  J  = 12.6, 8.1, 7.4, 7.2 Hz), 1.99 (ddddd,  J  = 10.3, 9.3, 7.4, 7.1, 5.4 Hz), 2.05 (ddddd,  J  = 10.3, 7.2, 5.5, 2.0, 1.4 Hz)), 3.71 (1H, ddd,  J  = 9.3, 6.6, 5.5 Hz), 3.86 (1H, ddd,  J  = 6.6, 5.4, 1.4 Hz), 4.10-4.36 (3H, 4.16 (d,  J  = 5.0 Hz), 4.16 (d,  J  = 5.0 Hz), 4.29 (dtd,  J  = 8.1, 5.0, 4.4 Hz)), 7.35 (1H, dd,  J  = 8.3, 8.1 Hz), 7.44-7.82 (7H, 7.51 (ddd,  J  = 7.9, 7.6, 1.4 Hz), 7.51 (dd,  J  = 8.3, 1.5 Hz), 7.53 (dddd,  J  = 8.0, 7.6, 1.7, 0.4 Hz), 7.57 (dd,  J  = 8.1, 1.5 Hz), 7.68 (dddd,  J  = 8.0, 1.4, 1.2, 0.4 Hz), 7.68 (ddt,  J  = 7.9, 1.7, 0.4 Hz), 7.77 (dt,  J  = 1.2, 0.4 Hz)). Determine the complete molecular structure.
Answer: O=C(c1cc2ccccc2o1)N(C[C@H]1CCCO1)c1nc2c(F)cccc2s1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C15H16N2O3S
Degree of Unsaturation (DoU): 9.0
Spectral Data:
- 13C NMR: δ 23.5 (1C, s), 25.7 (1C, s), 29.3 (1C, s), 34.4 (1C, s), 49.3 (1C, s), 65.8 (1C, s), 122.1 (1C, s), 122.3 (1C, s), 124.6 (1C, s), 126.2 (1C, s), 135.1 (1C, s), 152.9 (1C, s), 169.6 (1C, s), 173.7 (1C, s), 174.1 (1C, s)
- 1H NMR: δ 1.93-2.06 (2H, 1.99 (tt,  J  = 7.4, 7.0 Hz), 1.99 (tt,  J  = 7.4, 7.0 Hz)), 2.17-2.37 (4H, 2.26 (dddd,  J  = 14.0, 8.1, 7.3, 6.9 Hz), 2.23 (t,  J  = 7.4 Hz), 2.23 (t,  J  = 7.4 Hz), 2.28 (dddd,  J  = 14.0, 7.4, 4.3, 2.2 Hz)), 2.97-3.09 (2H, 3.03 (t,  J  = 7.0 Hz), 3.03 (t,  J  = 7.0 Hz)), 4.25-4.59 (3H, 4.33 (ddd,  J  = 13.8, 7.3, 2.2 Hz), 4.46 (dd,  J  = 8.1, 4.3 Hz), 4.51 (ddd,  J  = 13.8, 7.4, 6.9 Hz)), 7.26-7.45 (2H, 7.32 (td,  J  = 7.5, 1.5 Hz), 7.38 (ddd,  J  = 8.1, 7.5, 1.8 Hz)), 7.65-7.88 (2H, 7.71 (ddd,  J  = 7.5, 1.8, 0.5 Hz), 7.82 (ddd,  J  = 8.1, 1.5, 0.5 Hz)). Determine the complete molecular structure.
Answer: O=C(CCCc1nc2ccccc2s1)N[C@H]1CCOC1=O
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C16H20N2O4S
Degree of Unsaturation (DoU): 8.0
Spectral Data:
- 13C NMR: δ 19.4 (1C, s), 23.7 (1C, s), 35.4 (1C, s), 50.8 (1C, s), 51.1 (1C, s), 107.0 (1C, s), 118.5 (1C, s), 124.7 (1C, s), 124.9 (1C, s), 128.4 (1C, s), 128.7 (1C, s), 130.4 (1C, s), 130.7 (1C, s), 135.4 (1C, s), 140.4 (1C, s), 160.7 (1C, s)
- 1H NMR: δ 1.40 (3H, d,  J  = 6.6 Hz), 2.21 (3H, s), 3.75-3.90 (6H, 3.80 (s), 3.85 (s)), 5.20 (1H, q,  J  = 6.6 Hz), 6.86 (1H, d,  J  = 1.9 Hz), 6.98-7.22 (4H, 7.05 (ddd,  J  = 8.0, 7.6, 2.1 Hz), 7.07 (ddd,  J  = 7.9, 7.6, 1.6 Hz), 7.06 (ddd,  J  = 8.0, 1.6, 0.5 Hz), 7.16 (ddd,  J  = 7.9, 2.1, 0.5 Hz)), 8.34 (1H, d,  J  = 1.9 Hz). Determine the complete molecular structure.
Answer: COC(=O)c1cc(S(=O)(=O)N[C@H](C)c2ccccc2C)cn1C
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C18H18ClNO2
Degree of Unsaturation (DoU): 10.0
Spectral Data:
- 13C NMR: δ 21.3 (1C, s), 27.8 (1C, s), 42.0 (1C, s), 47.7 (1C, s), 70.0 (1C, s), 110.3 (1C, s), 124.7 (1C, s), 127.1 (2C, s), 128.6 (2C, s), 131.3 (1C, s), 133.9 (1C, s), 134.6 (1C, s), 135.7 (1C, s), 141.8 (1C, s), 142.0 (1C, s), 170.9 (1C, s)
- 1H NMR: δ 2.29 (3H, s), 2.69-2.80 (2H, 2.74 (d,  J  = 4.1 Hz), 2.74 (d,  J  = 4.1 Hz)), 3.08-3.25 (2H, 3.16 (ddd,  J  = 15.5, 8.1, 4.2 Hz), 3.16 (ddd,  J  = 15.5, 8.1, 4.2 Hz)), 3.75-3.92 (2H, 3.83 (ddd,  J  = 13.7, 8.1, 4.2 Hz), 3.83 (ddd,  J  = 13.7, 8.1, 4.2 Hz)), 4.73 (1H, t,  J  = 4.1 Hz), 6.73-6.88 (2H, 6.79 (dd,  J  = 7.9, 0.5 Hz), 6.82 (dd,  J  = 7.9, 1.4 Hz)), 7.19 (2H, ddd,  J  = 8.3, 1.1, 0.5 Hz), 7.39 (1H, dd,  J  = 1.4, 0.5 Hz), 7.53 (2H, ddd,  J  = 8.3, 1.4, 0.5 Hz). Determine the complete molecular structure.
Answer: Cc1ccc2c(c1)N(C(=O)C[C@H](O)c1ccc(Cl)cc1)CC2
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C10H12N4O5S
Degree of Unsaturation (DoU): 7.0
Spectral Data:
- 13C NMR: δ 61.5 (1C, s), 71.0 (1C, s), 74.8 (1C, s), 85.4 (1C, s), 92.0 (1C, s), 97.1 (1C, s), 149.3 (1C, s), 156.1 (1C, s), 163.3 (1C, s), 164.1 (1C, s)
- 1H NMR: δ 3.68 (1H, dt,  J  = 7.7, 6.4 Hz), 3.77-3.91 (3H, 3.82 (d,  J  = 6.4 Hz), 3.82 (d,  J  = 6.4 Hz), 3.84 (dd,  J  = 8.1, 7.7 Hz)), 4.25 (1H, dd,  J  = 8.1, 7.7 Hz), 5.69 (1H, d,  J  = 7.7 Hz), 8.25 (1H, s). Determine the complete molecular structure.
Answer: O=c1[nH]cnc2c1[nH]c(=S)n2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C19H18FN3OS
Degree of Unsaturation (DoU): 12.0
Spectral Data:
- 13C NMR: δ 26.6 (1C, s), 33.3 (1C, s), 43.6 (1C, s), 49.3 (1C, s), 51.0 (1C, s), 51.4 (1C, s), 107.0 (1C, s), 116.1 (1C, s), 122.2 (1C, s), 124.4 (1C, s), 125.6 (1C, s), 126.1 (1C, s), 127.7 (1C, s), 131.2 (1C, s), 144.0 (1C, s), 158.5 (1C, s), 159.3 (1C, s), 160.9 (1C, s), 190.6 (1C, s)
- 1H NMR: δ 2.18 (3H, s), 2.53 (1H, ddd,  J  = 15.1, 10.0, 3.7 Hz), 2.70-3.00 (3H, 2.78 (ddd,  J  = 15.1, 4.0, 1.9 Hz), 2.82 (ddd,  J  = 13.0, 10.0, 4.0 Hz), 2.92 (ddd,  J  = 13.0, 3.7, 1.9 Hz)), 3.01-3.22 (2H, 3.09 (dd,  J  = 11.0, 10.1 Hz), 3.15 (dd,  J  = 11.0, 3.7 Hz)), 3.73 (1H, dd,  J  = 10.1, 3.7 Hz), 3.85 (2H, s), 7.24-7.61 (5H, 7.32 (ddd,  J  = 7.9, 7.3, 1.2 Hz), 7.40 (d,  J  = 1.4 Hz), 7.42 (ddd,  J  = 8.3, 1.2, 0.6 Hz), 7.54 (ddd,  J  = 8.3, 7.3, 1.5 Hz), 7.54 (ddd,  J  = 7.9, 1.5, 0.6 Hz)), 7.77 (1H, d,  J  = 1.4 Hz). Determine the complete molecular structure.
Answer: CC(=O)c1cc(CN2CCC3=NN=C(c4ccccc4F)[C@@H]3C2)cs1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C15H25N3O3S
Degree of Unsaturation (DoU): 5.0
Spectral Data:
- 13C NMR: δ 15.5 (1C, s), 17.8 (1C, s), 24.2 (1C, s), 25.5 (2C, s), 36.8 (1C, s), 50.0 (2C, s), 51.4 (1C, s), 66.6 (1C, s), 110.3 (1C, s), 127.8 (1C, s), 136.6 (1C, s), 148.2 (1C, s), 150.4 (1C, s)
- 1H NMR: δ 0.98 (3H, d,  J  = 6.8 Hz), 1.39-1.60 (5H, 1.45 (d,  J  = 6.7 Hz), 1.53 (dtt,  J  = 13.1, 6.6, 2.7 Hz)), 1.65-1.82 (4H, 1.73 (ddddd,  J  = 12.7, 6.8, 6.6, 2.8, 2.7 Hz), 1.74 (ddddd,  J  = 12.7, 6.8, 6.6, 2.8, 2.7 Hz)), 1.91 (1H, qdt,  J  = 6.8, 6.6, 3.8 Hz), 3.22-3.38 (4H, 3.30 (dt,  J  = 14.5, 6.8 Hz), 3.32 (d,  J  = 3.8 Hz), 3.32 (d,  J  = 3.8 Hz)), 3.64 (2H, dt,  J  = 14.5, 2.8 Hz), 4.23 (1H, quint,  J  = 6.7 Hz), 6.50 (1H, dd,  J  = 7.2, 0.5 Hz), 7.92 (1H, dd,  J  = 7.2, 1.9 Hz), 8.56 (1H, dd,  J  = 1.9, 0.5 Hz). Determine the complete molecular structure.
Answer: C[C@H](Nc1ccc(S(=O)(=O)N2CCCCC2)cn1)[C@@H](C)CO
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C20H28N4O2
Degree of Unsaturation (DoU): 9.0
Spectral Data:
- 13C NMR: δ 11.2 (1C, s), 11.6 (1C, s), 21.0 (1C, s), 24.5 (1C, s), 34.4 (1C, s), 47.2 (1C, s), 47.6 (1C, s), 58.8 (1C, s), 59.0 (1C, s), 68.4 (1C, s), 116.0 (1C, s), 127.0 (1C, s), 127.8 (1C, s), 129.4 (1C, s), 133.5 (1C, s), 136.3 (1C, s), 137.4 (1C, s), 137.8 (1C, s), 149.8 (1C, s), 153.7 (1C, s)
- 1H NMR: δ 1.90-2.31 (13H, 1.99 (dddd,  J  = 12.4, 7.1, 5.6, 1.4 Hz), 2.01 (dtdd,  J  = 13.2, 9.2, 5.6, 5.4 Hz), 2.00 (dddt,  J  = 13.2, 5.7, 5.6, 1.4 Hz), 2.06 (s), 2.14 (dddd,  J  = 12.4, 9.2, 7.4, 5.7 Hz), 2.15 (s), 2.26 (s)), 3.21 (3H, s), 3.37-3.61 (2H, 3.44 (ddd,  J  = 14.8, 5.4, 1.4 Hz), 3.52 (ddd,  J  = 14.8, 9.3, 5.6 Hz)), 3.65-3.77 (2H, 3.71 (t,  J  = 6.4 Hz), 3.71 (t,  J  = 6.4 Hz)), 4.04-4.16 (2H, 4.10 (t,  J  = 6.4 Hz), 4.10 (t,  J  = 6.4 Hz)), 4.97 (1H, dd,  J  = 7.4, 7.1 Hz), 6.88 (1H, dt,  J  = 8.0, 1.6 Hz), 6.94-7.12 (2H, 7.00 (dt,  J  = 7.9, 1.6 Hz), 7.06 (td,  J  = 1.6, 0.5 Hz)), 7.26 (1H, td,  J  = 7.9, 0.5 Hz). Determine the complete molecular structure.
Answer: COCCn1nc(C)c(NC(=O)N2CCC[C@H]2c2cccc(C)c2)c1C
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C16H9FN4O2S2
Degree of Unsaturation (DoU): 14.0
Spectral Data:
- 13C NMR: δ 108.7 (1C, s), 116.8 (2C, s), 122.0 (2C, s), 126.7 (1C, s), 128.7 (1C, s), 131.2 (1C, s), 132.1 (1C, s), 148.9 (1C, s), 156.3 (1C, s), 159.9 (1C, s), 161.2 (1C, s), 163.0 (1C, s), 163.3 (1C, s), 171.0 (1C, s)
- 1H NMR: δ 6.35 (1H, d,  J  = 5.9 Hz), 7.04-7.18 (5H, 7.10 (dd,  J  = 8.0, 5.1 Hz), 7.10 (ddd,  J  = 8.2, 1.4, 0.5 Hz), 7.11 (ddd,  J  = 8.2, 1.9, 0.5 Hz)), 7.54-7.74 (2H, 7.60 (dd,  J  = 5.1, 1.2 Hz), 7.67 (dd,  J  = 8.0, 1.2 Hz)), 8.04 (1H, d,  J  = 5.9 Hz). Determine the complete molecular structure.
Answer: Fc1ccc(Oc2ccnc(Sc3nnc(-c4cccs4)o3)n2)cc1
Question: Given the following spectroscopic data for an unknown compound: 1 H NMR (200 MHz, CDCl3) δ 7.42-7.26 (m, 5H), 6.57 (d, J = 15.80, 1H), 6.28 (dt, J = 15.80, 6.40, 1H), 4.73 (dd, J = 6.40, 1.20, 2H), 2.10 (s, 3H); 13C NMR (50 MHz, CDCl3) δ 170.75, 136.20, 134.14, 128.56, 128.01, 126.55, 123.17, 64.91, 20.77; TLC Rf 0.29 (EtOAc/hexanes, 1/20). Determine the complete molecular structure.
Answer: CC(=O)OCC=Cc1ccccc1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C12H18NO2. 1H NMR (400 MHz, CDCl3): δ = 8.50 (d, J = 4.4 Hz, 1 H), 7.68 (t, J = 7.7 Hz, 1 H), 7.26 (d, J = 7.8 Hz, 1 H), 7.22 – 7.16 (m, 1 H), 4.19 (d, J = 13.9 Hz, 1 H), 4.01 (d, J = 13.9 Hz, 1 H), 2.13 – 2.02 (m, 1 H), 1.31 (s, 3 H), 1.01 (d, J = 6.7 Hz, 3 H), 0.80 (d, J = 6.8 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 212.7, 154.8, 148.7, 137.2, 124.3, 122.0, 81.2, 47.0, 34.8, 23.5, 17.1, 16.1. Determine the complete molecular structure.
Answer: CC(C)C(C)(O)C(=O)Cc1ccccn1
Question: Given the following spectroscopic data for an unknown compound: 1H NMR (500 MHz, CDCl3) δ 10.35 (s, 1H), 8.31 (d, J = 15.7 Hz, 1H), 6.79 (s, 1H), 6.74 (d, J = 15.6 Hz, 1H), 3.94 (s, 3H), 3.93 (s, 3H), 3.85 (s, 3H), 3.70 (s, 3H), 3.24 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 190.0, 166.2, 157.7, 157.5, 142.5, 142.3, 134.2, 121.5, 119.3, 106.9, 62.3, 61.8, 61.0, 56.2, 32.4; Determine the complete molecular structure.
Answer: COc1cc(C=CC(=O)N(C)OC)c(C=O)c(OC)c1OC
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C4H6O2. 1H NMR (400 MHz) δ 4.58 (d, 2 H, J = 12.3 Hz), 4.08 (ddd, 2 H, J = 11.4, 7.7, 6.9 Hz), 2.71 (ddd, 2 H, J = 7.7, 6.9, 14.4 Hz). Determine the complete molecular structure.
Answer: O=C1CCOC1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C7H7NO2. 1H NMR (400 MHz) δ 8.01 (ddd, 2 H, J = 8.2, 1.9, 0.5 Hz), 7.39 (ddd, 2 H, J = 8.2, 0.5, 1.5 Hz), 2.31 (3 H). Determine the complete molecular structure.
Answer: Cc1ccc([N+](=O)[O-])cc1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C13H12OSe. 1H NMR (CDCl3, 400 MHz): δ 7.50 (d, J = 8.8 Hz, 2H); 7.33-7.31 (m,
2H); 7.21-7.16 (m, 3H); 6.84 (d, J = 8.4 Hz, 2H); 3.79 (s, 3H). 13C NMR (CDCl3 100 MHz); δ (ppm): 159.7, 136.5, 133.2, 130.9, 129.1, 126.4, 119.9, 115.1, 55.2. MS (relative intensity)
m/z: 264 (65), 262 (34), 184 (100), 153 (32), 65 (14). Determine the complete molecular structure.
Answer: COc1ccc([Se]c2ccccc2)cc1
Question: Given the following spectroscopic data for an unknown compound: 1H-NMR (400 MHz, CDCl3) δH 8.80 (d, J = 0.7 Hz, 1H), 8.11 – 8.08 (m, 1H), 8.06 – 7.97 (m, 2H), 7.59 – 7.41 (stack, 3H). 13C{ 1 H}-NMR (101 MHz, CDCl3) δC 189.1 (CH), 155.8 (CH), 134.1 (C), 131.6 (CH), 130.5 (CH), 128.6 (CH), 105.9 (C). LRMS (ES+): 313.1 [(M + Na + MeOH)+ , 30%], 281.1 [100, (M + Na)+ ], 259.1 [40, (M + H)+ ]. Determine the complete molecular structure.
Answer: O=CC(I)=Cc1ccccc1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C10H11N. 1H NMR (CDCl3, 400 MHz) δ 7.71 (s, 1H), 7.53-7.51 (m, 1H), 7.24-7.18 (m, 1H), 7.12-7.04 (m, 2H), 6.22 (s, 1H), 2.75-2.69 (m, 2H), 1.32-1.28 (t, J = 8 Hz, 8 Hz, 3H); 13C NMR (CDCl3, 101 MHz) δ 141.5, 135.9, 128.8, 121.0, 119.8, 119.6, 110.2, 98.5, 21.3, 13.2. Determine the complete molecular structure.
Answer: CCc1cc2ccccc2[nH]1
Question: Given the following spectroscopic data for an unknown compound: Molecular Formula: C9H12N2. 1H NMR (400 MHz, CDCl3) δ 2.95-2.87 (m, 1H ), 2.80 – 2.61 (m, 2H), 2.28 – 2.10 (m, 1H), 2.05 – 1.81 (m, 2H), 1.81 – 1.51 (m, 4H), 1.51 – 1.19 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 118.5, 115.9, 41.0, 33.6, 30.9, 29.7, 25.2, 25.0, 20.5. HR-MS (ESI) (M+NH4) + : calc. 166.1339, found 166.1338. Determine the complete molecular structure.
Answer: N#CCC(C#N)C1CCCC1
Question: Given the following spectroscopic data for an unknown compound: 1H NMR (600 MHz, DMSO) δ 12.77 (s, 1H), 7.81 (dd, J = 7.8, 1.5 Hz, 1H), 7.43 (td, J = 7.5, 1.5 Hz, 1H), 7.30 – 7.25 (m, 2H), 2.51 (s, 3H). 13C NMR (150 MHz, DMSO) δ 168.7, 139.0, 131.7, 131.5, 130.5, 130.2, 125.8, 21.3. Determine the complete molecular structure.
Answer: Cc1ccccc1C(=O)O