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Massachusetts Institute of Technology Organic Chemistry 5.13 September 18 and 20, 2006 Prof. Timothy F. Jamison Notes for Lectures #6 and #7 1 H NMR Spectroscopy Spin-Spin Coupling and Connectivity Signature Splitting Patterns in 1H NMR Spectra Prof. Timothy F. Jamison Notes for Lectures #6 and #7 'H NMR Spectroscopy - Spin-Spin Coupling and Connectivity
Signature "Splitting" Patterns in 'H NMR Spectra
Singlet, 3H Methyl group CH3-Z Z= non H-bearing atom; typically O, N, C of Ar, etc.
Quartet (2H) and Triplet (3H) Ethyl group CH3CH2-Z Z= non H-bearing atom, typically O, N, C of Ar, etc.
Quadet (2H) and Triplet (3H) Ethyl group CH3CH2-Z Z = non H-bearing atom, typically 0, N, C of Ar, etc.
CH3-Z
Septet (1H) and Doublet (6H) Isopropyl group (CH3)2CH-Z Z = non H-bearing atom,typically O, N, C of Ar, etc.
Doublet of Doublets (1H) Proton coupled to two non-equivalent protons which are attached to the same or different atoms
Doublet of Daublets (1H) Proton coupled to two non-equivalent protons which are attached to the same or dmerent
atoms
Two Triplets (each 2H) Adjacent methylene groups 1 2 Z -CH2CH2 -Z 1 2 Z , Z = very different non H-bearing atoms
Two 1 riplets (each 2H) Adjacent rnethylene grw ps Z'-CH~CH~Z* Z'
,' 2 = ver)r different
Two Triplets (each 2H) and Quintet (2H) Three adjacent 1 2 methylene groups Z -CH2CH2CH2-Z 1 2 Z , Z = very different non H-bearing atoms
Two Triplets (each 2H) and Quintet (2H) f hree adjacent methylene groups Z'-CH~CH~C H ~ - Zby ~ MIT OCW. Figure z'. z2= very different non H-bearing atoms
In rigid systems, vicinal coupling can range from 0 to 15 Hz. For example:
H ax-ax 6-14 Hz H H ax-eq 0-5 Hz H H
eq-eq 0-5 Hz
allylic 0-3 Hz
Ha C C Hb
Ho
Direction of applied magnetic field
Hb
Hb
Hb