常用波谱数据表

小木虫经典出品 (C) emuch.net Infrared Spectroscopy IR Absorptions for Representative Functional Groups Functional Group Molecular Motion Wavenumber (cm )-1 C-H stretch 2950-2800 CH2 bend ~1465 CH3 bend ~1375 alkanes CH2 bend (4 or more) ~720 =CH stretch 3100-3010 C=C stretch (isolated) 1690-1630 C=C stretch (conjugated) 1640-1610 C-H in-plane bend 1430-1290 C-H bend (monosubstituted) ~990 & ~910 C-H bend (disubstituted - E) ~970 C-H bend (disubstituted - 1,1) ~890 C-H bend (disubstituted - Z) ~700 alkenes C-H bend (trisubstituted) ~815 acetylenic C-H stretch ~3300 C,C triple bond stretch ~2150 alkynes acetylenic C-H bend 650-600 C-H stretch 3020-3000 C=C stretch ~1600 & ~1475 C-H bend (mono) 770-730 & 715-685 C-H bend (ortho) 770-735 C-H bend (meta) ~880 & ~780 & ~690 aromatics C-H bend (para) 850-800 1 小木虫经典出品 (C) emuch.net O-H stretch ~3650 or 3400-3300 alcohols C-O stretch 1260-1000 C-O-C stretch (dialkyl) 1300-1000 ethers C-O-C stretch (diaryl) ~1250 & ~1120 C-H aldehyde stretch ~2850 & ~2750 aldehydes C=O stretch ~1725 C=O stretch ~1715 ketones C-C stretch 1300-1100 O-H stretch 3400-2400 C=O stretch 1730-1700 C-O stretch 1320-1210 carboxylic acids O-H bend 1440-1400 C=O stretch 1750-1735 C-C(O)-C stretch (acetates) 1260-1230 esters C-C(O)-C stretch (all others) 1210-1160 C=O stretch 1810-1775 acid chlorides C-Cl stretch 730-550 C=O stretch 1830-1800&1775-1740 anhydrides C-O stretch 1300-900 N-H stretch (1 per N-H bond) 3500-3300 N-H bend 1640-1500 C-N Stretch (alkyl) 1200-1025 C-N Stretch (aryl) 1360-1250 amines N-H bend (oop) ~800 N-H stretch 3500-3180 C=O stretch 1680-1630 N-H bend 1640-1550 amides N-H bend (1o) 1570-1515 2 小木虫经典出品 (C) emuch.net C-F stretch 1400-1000 C-Cl stretch 785-540 C-Br stretch 650-510 alkyl halides C-I stretch 600-485 nitriles C,N triple bond stretch ~2250 isocyanates -N=C=O stretch ~2270 isothiocyanates -N=C=S stretch ~2125 imines R2C=N-R stretch 1690-1640 -NO2 (aliphatic) 1600-1530&1390-1300 nitro groups -NO2 (aromatic) 1550-1490&1355-1315 mercaptans S-H stretch ~2550 sulfoxides S=O stretch ~1050 sulfones S=O stretch ~1300 & ~1150 S=O stretch ~1350 & ~11750 sulfonates S-O stretch 1000-750 P-H stretch 2320-2270 phosphines PH bend 1090-810 phosphine oxides P=O 1210-1140 II. NMR Solvent Signals The chemical shifts (d) of solvent signals observed for 1H NMR and 13C NMR spectra are listed in the following table. The multiplicity is shown in parentheses as 1 for singlet, 2 for doublet, 3 for triplet, etc. Solvent 1H NMR Chemical Shift 13C NMR Chemical Shift Acetic Acid 11.65 (1) , 2.04 (5) 179.0 (1) , 20.0 (7) Acetone 2.05 (5) 206.7 (13) , 29.9 (7) Acetonitrile 1.94 (5) 118.7 (1) , 1.39 (7) Benzene 7.16 (1) 128.4 (3) Chloroform 7.26 (1) 77.2 (3) 3 小木虫经典出品 (C) emuch.net Dimethyl Sulfoxide 2.50 (5) 39.5 (7) Methanol 4.87 (1) , 3.31 (5) 49.1 (7) Methylene Chloride 5.32 (3) 54.00 (5) Pyridine 8.74 (1) , 7.58 (1) , 7.22 (1) 150.3 (1) , 135.9 (3) , 123.9 (5) Water (D2O) 4.8 III. NMR Water Signals Signals for water occur at different frequencies in 1H NMR spectra depending on the solvent used. Listed below are the chemical shift positions of the water signal in several common solvents. Note that H2O is seen in aprotic solvents, while HOD is seen in protic solvents due to exchange with the solvent deuteriums. Solvent Chemical Shift of H2O (or HOD) Acetone 2.8 Acetonitrile 2.1 Benzene 0.4 Chloroform 1.6 Dimethyl Sulfoxide 3.3 Methanol 4.8 Methylene Chloride 1.5 Pyridine 4.9 Water (D2O) 4.8 4 小木虫经典出品 (C) emuch.net 1H-Chemical Shifts relativ to TMS 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 H3C-Alkyl H3C-C-Hal H3C-C=C H3C-CC H3C-Aryl,-Heteroaryl H3C-CO H3C-S- H3C-SO2- H3C-N 5 小木虫经典出品 (C) emuch.net H3C-O-Alkyl H3C-O-Aryl, -O-CO- C-CH2-Alkyl Cyclopropane C-CH2-CO C-CH2-O- C-CH2-S C-CH2-NO2 C-CH2-N C=C-CH2-C=C N-CH2-CO- -O-CH2-CO- -O-CH2-O-, -Aryl 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 CH-Alkyl CH-Hal C-CH-O- C-CH-N CO-CH-C=C CH-Aryl,-NR-,-O- -CCH Alkine CH=C- Ar-H Alkyl-, Aryl-CHO Alkyl-OH Aryl-OH R-COOH Alkyl-SH Aryl-SH Alkyl-NH2, Alkyl2-NH Aryl-NH2, Aryl2-NH R-CO-NH- -CO-NH-CO 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 6 小木虫经典出品 (C) emuch.net 13C Chemical Shifts relative to TMS 220 200 180 160 140 120 100 80 60 40 20 0 -20 H3C-C- primary H3C-S- H3C-N H3C-O- -H2C-C secondary Cyclopropanes -H2C-S- -H2C-N -H2C-O- -H2C-Hal F Cl Br I >CH-C- tertiary >CH-S- >CH-N >CH-Hal F Cl Br I C-C quarternary C-S- C-N C-O- C-Hal Cl Br I relative to TMS 220 200 180 160 140 120 100 80 60 40 20 0 -20 Alkines C=C=C Allenes C=C Alkenes Aromatic Compounds Heteroaromatic Compounds -S-CN Rhodanides -N=C=S Isothiocyanates -O-CN -N=C=O 7 小木虫经典出品 (C) emuch.net -CN -NC >C=N- Azomethines (-CO)2O Anhydrides -COOR -CONHR -(CO)2NR Imides -COOH -COCl -CHO >C=O relative to TMS 220 200 180 160 140 120 100 80 60 40 20 0 -20 nJH,H-Coupling Constants Absolute values are given. most probable sign: I. 2JH,H- Coupling constants mostly negative II. 3JH,H- Coupling constants mostly positive III. n>3JH,H- Coupling constants positve/negative Type J (Hz) Type J ( Hz) 12-15 2-9 0 6,5- 7,5 5,5- 7,0 • aa 5-8 • ae 2-4 • ee 2-4 8 小木虫经典出品 (C) emuch.net 0,5- 3 7-12 13-18 4-10 0,5- 2,5 0 9- 13 2- 3 1- 3 2- 4 • o 6- 9 • m 1- 3 • p 0- 1 • 1-2 1,6-2,0 • 1-3 0,6-1,0 • 1-4 1,3-1,8 • 2-3 3,2-3,8 • 1-2 2,0-2,6 • 1-3 1,5-2,2 • 1-4 1,8-2,3 • 2-3 2,8-4,0 • 1-2 4,6-5,8 • 1-3 1,0-1,8 • 1-4 2,1-3,3 • 2-3 3,0-4,2 • 1-2 4,9-5,7 • 1-3 1,6-2,6 • 1-4 0,7-1,1 • 1-5 0,2-0,5 • 2-3 7,2-8,5 • 2-4 1,4-1,9 Characteristic IR Band Positions 9 小木虫经典出品 (C) emuch.net Group Frequency Range (cm-1) OH stretching vibrations Free OH 3610-3645 (sharp) Intramolecular H bonds 3450-3600 (sharp) Intermolecular H Bonds 3200-3550 (broad) Chelate Compounds 2500-3200 (very broad) NH Stretching vibrations Free NH 3300-3500 H bonded NH 3070-3350 CH Stretching vibrations =-C-H 3280-3340 =C-H 3000-3100 C-CH3 2862-2882, 2652-2972 O-CH3 2815-2832 N-CH3 (aromatic) 2810-2820 N-CH3 (aliphatic) 2780-2805 CH2 2843-2863,2916-2936 CH 2880-2900 SH Stretching Vibrations Free SH 2550-2600 C=-N Stretching Vibrations Nonconjugated 2240-2260 Conjugated 2215-2240 C=-C Stretching Vibrations C=-CH (terminal) 2100-2140 C-C=-C-C 2190-2260 C-C=-C-C=-CH 2040-2200 C=O Stretching Vibrations Nonconjugated 1700-1900 Conjugated 1590-1750 Amides ~1650 C=C Sretching Vibrations 10 小木虫经典出品 (C) emuch.net Nonconjugated 1620-1680 Conjugated 1585-1625 CH Bending Vibrations CH2 1405-1465 CH3 1355-1395, 1430-1470 C-O-C Vibrations in Esters Formates ~1175 Acetates ~1240, 1010-1040 Benzoates ~1275 C-OH Stretching Vibrations Secondary Cyclic Alcohols 990-1060 CH out-of-plane bending vibrations in substituted ethylenic systems -CH=CH2 905-915, 985-995 -CH=CH-(cis) 650-750 -CH=CH-(trans) 960-970 C=CH2 885-895 11 Infrared Spectroscopy IR Absorptions for Representative Functional Groups 1H-Chemical Shifts 13C Chemical Shifts nJH,H-Coupling Constants