Method for Determining the Deuterium Substitution Rate According to Substitution Positions

Abstract

The present disclosure relates to a method for analysis of a deuterium substitution rate of a deuterium-substituted sample according to substitution positions using information of a .sup.1H-NMR spectrum of the deuterium-substituted sample.

Claims

1. A method for determining the deuterium substitution rate of a deuterium-substituted sample according to substitution positions, comprising: obtaining a .sup.1H-NMR spectrum of the deuterium-substituted sample (step 1); and calculating a deuterium substitution rate ([D %].sub.p) of the deuterium-substituted sample according to substitution positions from the following Equation 1 using information of the .sup.1H-NMR spectrum (step 2):
[D %].sub.p=100−((100−[D %])×A.sub.p×H)/(A×H.sub.p)  [Equation 1] wherein, in Equation 1, [D %] is an average deuterium substitution rate of the deuterium-substituted sample, A.sub.p is an integration value of a peak at the position in the .sup.1H-NMR spectrum, H is a total number of hydrogens in the deuterium-substituted sample before deuterium substitution, A is a sum of integration values of each peak in the .sup.1H-NMR spectrum, H.sub.p is a number of hydrogens at the position in the deuterium-substituted sample before deuterium substitution.

2. The method of claim 1, wherein the deuterium-substituted sample is a sample in which deuterium is substituted in at least one position where hydrogen is substituted in a molecular structure.

3. The method of claim 1, wherein the deuterium-substituted sample has two or more positions where hydrogen is substituted in a molecular structure.

4. The method of claim 1, wherein the deuterium-substituted sample is deuterium-substituted anthracene.

5. The method of claim 1, wherein the average deuterium substitution rate of the deuterium-substituted sample is obtained by an analysis method of MS, GC/MS, or HPLC.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0037] FIG. 1s a .sup.1H-NMR spectrum of deuterium-substituted anthracene, which is a sample used in Example of the present disclosure.

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0038] Hereinafter, the embodiment of the present invention will be described in more detail in the following examples. However, these examples are for illustrative purposes only, and the invention is not intended to be limited by these examples.

Example: Analysis of Deuterium Substitution Rate of Anthracene According to Substitution Positions

[0039] The following experiment was performed using deuterium-substituted anthracene (Anthracene-d10; manufactured by Sigma-Aldrich; Product number 176591; CAS number 1719-06-8; average deuterium substitution rate: 99.1%).

[0040] .sup.1H-NMR spectrum of the deuterium-substituted anthracene was measured, and the results are shown in FIGURE. The measurement conditions are as follows. [0041] pulse sequence=zg30 [0042] number of scan (ns)=32 [0043] relaxation delay (d1)=10.0 sec [0044] acquisition time (aq)=2.3 sec [0045] temperature=298 K

[0046] The information in Table 1 below was obtained from FIGURE. As shown in Table 1 below, A1, A2, and B1 refer to positions at which deuterium is substituted in anthracene, respectively.

TABLE-US-00001 TABLE 1 [00001] Sum of integration values of each peak in A: 7.69 .sup.1H-NMR spectrum Total number of protons in structure before H: 10 deuterium substitution Integration value corresponding to each peak A.sub.B1: 1.00 A.sub.A1: 4.33 A.sub.A2: 2.36 Number of protons corresponding to each peak H.sub.B1: 2 H.sub.A1: 4 H.sub.A2: 4 Avg. deuterium substitution rate D %: 99.1

[0047] (1) Deuterium Substitution Rate at Position B1

[0048] The deuterium substitution rate at position B1 can be calculated as follows.

[00001]${\left[D\%\right]}_{B1}=100-\frac{\left(100-99.1\right)*1.00*10}{7.69*2}=99.4\%$

[0049] The calculation will be described in more detail as follows.

[0050] First, the average number of moles of protons remaining unsubstituted with deuterium in the deuterium-substituted anthracene is calculated.

[00002]${\left[\mathrm{mol}\right]}_a=\frac{A}{H}$

[0051] [H %].sub.B1 remaining unsubstituted with deuterium at position B1 is calculated.

[00003]${\left[H\%\right]}_{B1}=\frac{\left(100-\left[D\%\right]*A_{B1}\right)}{{\left[\mathrm{mol}\right]}_a*H_{B1}}=\frac{\left(100-\left[D\%\right]\right)*A_{B1}*H}{A*H_{B1}}$

[0052] Then, the deuterium substitution rate (%) at B1 is calculated by subtracting the above value from 100.

[D %].sub.B1=100−[H %].sub.B1

[0053] In the same way, the deuterium substitution rates at position A1 and position A2 can be calculated as follows.

[0054] (2) Deuterium Substitution Rate at Position A1

[00004]${\left[D\%\right]}_{A1}=100-\frac{\left(100-99.1\right)*4.33*10}{7.69*4}=98.7\%$

[0055] (3) Deuterium Substitution Rate at Position A2

[00005]${\left[D\%\right]}_{A2}=100-\frac{\left(100-99.1\right)*2.36*10}{7.69*4}=99.3\%$