Blog on Hiatus from July 26 to August 6, 2010

Due to some business travel, the blog P2C2E will be on hiatus for 2 weeks from July 26 to August 6. Posts will resume the following week.

Stay tuned for more logic puzzles.

Logic Puzzle #5: Coupling + Tilting + Integration = Benzene … Solution

The goal of this puzzle is to determine the respective benzene ring systems that would exhibit the following 1H NMR spectrum.

The number of substituted benzene ring systems that would exhibit the following 1H NMR spectrum is 3 (assuming no repeating units). The keys to solving this puzzle lie with the determination of which multiplets are coupled in combination with the integral information.

 

Starting with the easy set of multiplets, M08 and M07 are coupled to each other. The second order effects (evident by tilting towards each other) and the similar coupling constants (roughly +/- 0.2 Hz) support this claim. Along side the integral ratio of 2:2, this pattern is intrinsic for a para-substituted benzene ring. Next, the multiplets M01, M03 and M05 are coupled. The 1:2:2 integral ratio and identical coupling constants support a mono-substituted benzene ring. Finally, M02, M04 and M06 are coupled. The 1:1:1 integral ratio and meta-coupling pattern (post#2 link) indicate the presence of a 1,2,4-trisubstituted benzene ring system.

Logic Puzzle #5: Coupling + Tilting + Integration = Benzene

The goal of this puzzle is to determine the respective benzene ring systems that would exhibit the following 1H NMR spectrum.

For the following aromatic region of the 1H NMR spectrum, how many benzene ring systems are present?

Logic Puzzle #5: Coupling + Tilting + Integration = Benzene

The goal of this puzzle is to determine the respective benzene ring systems that would exhibit the following 1H NMR spectrum.

For the following aromatic region of the 1H NMR spectrum, how many benzene ring systems are present?

Logic Puzzle #4: Correlating to the Correct 13C Signal … Solution

The goal of this puzzle is to resolve the ambiguity exhibited within a 2D NMR spectrum and thus provide the correct signal correlation. Although this exercise may seem a trivial one, it is important to go over the rationale when correlating one signal to another.

For the following 1H-13C HSQC-DEPT NMR spectrum it is important to note that the 2 correlations are phased positively (red) and thus represent either a CH or CH3 group and not a CH2. Next, one must ensure that the carbons at 61.5 and 62.2 ppm are 1 carbon each. Although this detail is not certain, we will assume this to be the case. Finally, it is best to start with the easy part first. The 1H signal at 3.50 ppm is correlated to the 13C signal at 62.2 ppm. By process of elimination, one can conclude that the 1H signal at 2.73 ppm is correlated to the 13C signal at 61.5 ppm (see this post for more details).

Ambiguity in correlating 1D and 2D NMR data can routinely occur. Some extra steps that can help avoid this issue are re-aligning the data and/or re-processing the ‘raw’ data with different parameters.

 

Logic Puzzle #4: Correlating to the Correct 13C Signal … Solution

The goal of this puzzle is to resolve the ambiguity exhibited within a 2D NMR spectrum and thus provide the correct signal correlation. Although this exercise may seem a trivial one, it is important to go over the rationale when correlating one signal to another.

For the following 1H-13C HSQC-DEPT NMR spectrum it is important to note that the 2 correlations are phased positively (red) and thus represent either a CH or CH3 group and not a CH2. Next, one must ensure that the carbons at 61.5 and 62.2 ppm are 1 carbon each. Although this detail is not certain, we will assume this to be the case. Finally, it is best to start with the easy part first. The 1H signal at 3.50 ppm is correlated to the 13C signal at 62.2 ppm. By process of elimination, one can conclude that the 1H signal at 2.73 ppm is correlated to the 13C signal at 61.5 ppm (see this post for more details).

Ambiguity in correlating 1D and 2D NMR data can routinely occur. Some extra steps that can help avoid this issue are re-aligning the data and/or re-processing the ‘raw’ data with different parameters.