Method for Determining The Average Deuterium Substitution Rate

Abstract

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

Claims

1. A method for determining the average deuterium substitution rate of a deuterium-substituted sample, comprising: obtaining .sup.1H-NMR spectra of the deuterium-substituted sample and a standard sample, respectively (step 1); and calculating an average deuterium substitution rate ([D %]) of the deuterium-substituted sample from the following Equations 1 and 2 using information of the .sup.1H-NMR spectra (step 2): $\begin{array}{cc}D=\frac{{\mathrm{SA}}_H-{\mathrm{SA}}_M*\left(\frac{{\mathrm{SA}}_I}{{\mathrm{IS}}_I}*\frac{{\mathrm{IS}}_W}{{\mathrm{SA}}_W}*\frac{{\mathrm{IS}}_H}{{\mathrm{IS}}_M}\right)}{1+\left(\frac{{\mathrm{SA}}_I}{{\mathrm{IS}}_I}*\frac{{\mathrm{IS}}_W}{{\mathrm{SA}}_W}*\frac{{\mathrm{IS}}_H}{{\mathrm{IS}}_M}\right)}& \left[\mathrm{Equation}1\right]\\ \left[D\%\right]=\left(D/{\mathrm{SA}}_H\right)\times 100& \left[\mathrm{Equation}2\right]\end{array}$ wherein Equation 1, IS.sub.W is a weight of the standard sample, IS.sub.I is a .sup.1H-NMR integration value of a specific peak of the standard sample, IS.sub.M is a molecular weight of the standard sample, IS.sub.H is a number of hydrogens in a molecule in a specific peak of the standard sample, SA.sub.W is a weight of the deuterium-substituted sample, SA.sub.I is a .sup.1H-NMR integration value of the deuterium-substituted sample, SA.sub.M is a molecular weight of the deuterium-substituted sample before deuterium substitution, and SA.sub.H is a number of hydrogens in a molecule in the deuterium-substituted sample before deuterium substitution.

2. The method of claim 1, wherein the step 1 is performed by mixing the deuterium-substituted sample and the standard sample, and then obtaining a .sup.1H-NMR spectrum thereof.

3. The method of claim 2, wherein the deuterium-substituted sample and the standard sample is mixed in a weight ratio of 1:100 to 100:1.

4. The method of claim 2, wherein the deuterium-substituted sample and the standard sample is mixed in a weight ratio of 1:10 to 10:1.

5. The method of claim 1, wherein the SA.sub.W is a weight of the deuterium-substituted sample used to obtain the .sup.1H-NMR spectra in step 1, and IS.sub.W is a weight of the standard sample used to obtain the .sup.1H-NMR spectra in step 1.

6. The method of claim 1, wherein the standard sample is dimethyl acetamide.

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

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0041] FIG. 1 is a .sup.1H-NMR spectrum measured in Example of the present disclosure.

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0042] 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 Average Deuterium Substitution Rate of Anthracene

[0043] The following experiment was performed using deuterium-substituted anthracene (Anthracene-d10; manufactured by Sigma-Aldrich; Product number 176591; CAS number 1719-06-8).

[0044] Deuterium-substituted anthracene (3.14 mg) and dimethyl acetamide (DMAc; 10.97 mg) as a standard sample were accurately quantified and mixed, and then .sup.1H-NMR spectrum was measured. The results are shown in FIG. 1, and the measurement conditions are as follows. [0045] pulse sequence=zg30 [0046] number of scan (ns)=32 [0047] relaxation delay (d1)=10.0 sec [0048] acquisition time (aq)=2.3 sec [0049] temperature=298 K

[0050] In FIG. 1, hydrogen substituted at carbon 1 among the peaks of the standard sample was used as a reference. The information in Table 1 below was obtained from FIG. 1.

TABLE-US-00001 TABLE 1 Deuterium- substituted Dimethyl anthracene acetamide SA.sub.W: Weight (mg) 3.14 IS.sub.W: Weight (mg) 10.97 SA.sub.I: .sup.1H-NMR integration 7.69 IS.sub.I: .sup.1H-NMR integration value of 1908.92 value specific peak Molecular weight 178 + D IS.sub.M: Molecular weight 87 Number of hydrogens in 10 − D IS.sub.H: Number of hydrogens in 3 molecule molecule in specific SA.sub.M: Molecular weight before 178 peak deuterium substitution SA.sub.H: Number of hydrogens 10 before deuterium substitution

[0051] The D value was 9.91 by substituting the information obtained above into Equation 1, and the average deuterium substitution rate of anthracene was analyzed to be 99.1% by substituting the information obtained above into Equation 2.