DGD10_NZ

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Jan 9, 2024

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1 uOttawa.ca CHM3122: Applications of Spectroscopy • DGD10, Nov 21 st , 5:30 pm Presented by: Niayesh Zarifi

2 nzarifi@uottawa.ca Nuclear Overhauser effect (nOe) • Through-space phenomenon • Increases signals of nuclei with positive magnetogyric ratios (gamma) • Can help figure out if two nuclei are close together in space

3 nzarifi@uottawa.ca 13 C NMR • 13 C has a natural abundance of approximately 1% • – 13 C NMR spectra require more time/ more concentrated samples • Much simpler than 1 H NMR • Non-quantitative (usually) • 13 C NMR takes advantage of nOe

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4 nzarifi@uottawa.ca 13 C NMR and nOe • Since 1 H is nearly 100% abundant, we can use it to boost the signal of nearby 13 C nuclei • – “Proton-decoupled 13 C NMR” or 13 C{1H} NMR • – This is why 13 C NMR is usually non-quantitative! • Intensity of signals in 13 C NMR: – CH 3 ≌ CH 2 >> CH > C

5 nzarifi@uottawa.ca 13 C NMR: Example

6 nzarifi@uottawa.ca “Off resonance decoupling” and DEPT Use “off resonance decoupling” (old method) or DEPT (newer method) to assign C/ CH/ CH 2 /CH 3 signals!

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7 nzarifi@uottawa.ca DEPT 135 Most frequently used and useful experiment!

8 nzarifi@uottawa.ca Question 1 Predict the number of peaks expected in 13 C NMR spectrum:

9 nzarifi@uottawa.ca Question 2 Identify the alcohol with the formula C 4 H 10 O that corresponds to the following spectrum.

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10 nzarifi@uottawa.ca Question 2 Identify the alcohol with the formula C 4 H 10 O that corresponds to the following spectrum.

11 nzarifi@uottawa.ca Question 2 Identify the alcohol with the formula C 4 H 10 O that corresponds to the following spectrum.

12 nzarifi@uottawa.ca Question 3 C 7 H 16 O (the peak at 2.76 ppm disappears upon addition of D 2 O)

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13 nzarifi@uottawa.ca Question 4 A natural product C 12 H 13 NO 3 isolated from a rare species of cyanobacteria shows the following spectral characteristics. Identify the structure. IR 3338, 1715, 1592 cm -1 ; 1 H NMR (200 MHz, DMSO-d6) 12.7 (br, exch, 1H), 8.42 (d, exch, J = 6.1 Hz, 1H).7.45-7.25 (m, 5H), 6.63 (dd, J = 15.9, 1.2 Hz, 1H), 6.30 (dd, J = 15.9, 6.7 Hz, 1H), 4.93 (ddd, J = 6.7, 6.1, 1.2 Hz, 1H), 1.90 (s, 3H); 13C NMR (50 MHz, DMSO-d6) 171.9 (C), 169.0 (C), 135.9 (C), 131.7 (CH), 128.7 (CH), 127.9 (CH), 126.3 (CH), 124.6 (CH), 54.4 (CH), 22.3 (CH3).

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