第六章 有机化合物的结构解析.ppt

第六章 有机化合物结构解析 1-己炔 CH3(CH2)6CH3 2960cm-1 2930cm-1 1467cm-1 1380cm-1 (E)-2-己烯 (Z)-3-己烯 2-甲基-1-丙烯 Ar－H (stretch) C=C (stretch) C—H ( bending) (Monosubstituted benzene) Toluene IR(neat) 3030, 1610, 1490, 730(s), 690(s). ～ υ (cm-1) : 2-Methyl-2-propanol O—H (stretch) C—O (stretch) C—H (stretch) 6.4 核磁共振谱 Nuclear Magnetic Resonance Spectroscopy (NMR) NMR谱图给出的结构信息: 化学位移、峰面积、自旋裂分和偶合常数 不同化学环境的核，受到不同程度的屏蔽效应，其共振吸收的位置不同，这种位置的差异为化学位移。 6.4.2 化学位移 The chemical shifts (1) Representation of the Chemical Shift δTMS＝ 0, 其它化学位移在其左侧。 Definition： The shift of absorption signal of proton by shielding and deshileding effect. Unit: ppm (part per million) 百万分之一 (2) Relation of molecular structure with 1H chemical shifts: Different environments of protons in the mole, different degrees of shielding in the experiment, different chemical shifts. 分子中质子的化学环境不同，质子所受到的屏蔽效应的程度不同，其化学位移值不同。 (a) Effects of electronegativity Increased shielding of methyl protons Decreasing electronegativity of attached atom δ CH3CH3 (CH3)3N CH3OCH3 CH3F 0.9 2.2 3.2 4.3 (b) 磁各向异性效应 CH3CH3 δ 7.3 5.3 2.0~3.0 0.9 苯的各向异性效应 B0 B0 乙炔的各向异性效应 CH3R R2CH2 1.8 CH3C = C 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 δ 0.9 1.25 1.5 R3CH 2.1 2~3 3.0 3.7 CH3O－ 4.5~6.5 Ar－H 10~13 RCOOH 0.5~5.5 ROH 0.4~3.5 一些官能团中质子的化学位移 CH3OCH2CN 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 Chemical shift (δ, ppm) 4.1 3.3 Chemical nonequivalent 15mm H1:H2=2:3 10mm (3)Intepreting proton NMR spectra (氢谱解析) Information about the mole. Structure by 1HNMR spectra: The number of signals－the kind of proton; 2. Intergration of the area under each peak－ relative ratios of different protons; CH3CH2CHCH2Br Cl How many signals on NMR spectra? δ 5.3 ppm δ 5.5 ppm 2-Bromopropene Enantiomers * *