Multi-element standard for nuclear magnetic resonance spectroscopy

Patent metadata

Field	Value
Publication number	US-10040811-B2
Application number	US-201314387520-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 23, 2012
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

Organic compounds which contain nitrogen, fluorine, and phosphorus atoms together with carbon atoms and hydrogen atoms and which can be used as a multi-element standard for 1 H—, 13 C—, 15 N—, 19 F—, and 31 P nuclear magnetic resonance spectroscopy. Also, a nuclear magnetic resonance spectroscopy method, preferably a quantitative nuclear magnetic resonance spectroscopy method, using said compounds and a method for qualitatively and/or quantitatively determining an analyte using such a nuclear magnetic resonance spectroscopy method.

First claim

The invention claimed is:

1. A method of identifying an analyte wherein the method comprises:
providing a standard compound for nuclear magnetic resonance spectroscopy, the standard compound comprised of the formula (1) or (2)

where R 1 is a phenyl radical or benzyl radical whose benzene ring has the following substituents:
at least one —CF 3 substituent,
at least one nitrogen-containing substituent selected from —NO 2 and —NR 4 R 5 , where R 4 and R 5 independently of one another are selected from H, CH 3 , and CH 2 CH 3 , optionally one or two substituents selected from Cl, Br, I, —CH 3 , and —C(═O)OR 6 , where R 6 is selected from H, CH 3 , and CH 2 CH 3 , and
at least one hydrogen atom, where at least one of the hydrogen atoms is ortho to at least one substituent selected from —NO 2 and —C(═O)OR 6 , and
where R 2 and R 3 are the same as R 1 or independently of one another are selected from H, CH 3 , and CH 2 CH 3 ;
detecting the nuclear magnetic resonance of one of the atoms 1 H, 13 C, 15 N, 19 F, or 31 P; and
determining the analyte quantitatively.

2. The method according to 1 , wherein the benzene ring carries precisely two hydrogen atoms as substituents.

3. The method according to claim 2 , wherein the two hydrogen atoms are meta to one another on the benzene ring.

4. The method according to claim 1 , wherein at least one hydrogen atom on the benzene ring is ortho to at least one CF 3 substituent or CH 3 substituent.

5. The method according to claim 1 , wherein at least two hydrogen atoms on the benzene ring are ortho to at least one CF 3 substituent or CH 3 substituent.

6. The method according to claim 1 , wherein at least two hydrogen atoms on the benzene ring are ortho to at least one substituent selected from —NO 2 and —C(═O)OR 6 .

7. The method as claimed in claim 1 , wherein the benzene ring carries only one hydrogen atom as substituent, and the hydrogen atom on the benzene ring is preferably ortho to at least one CF 3 substituent or CH 3 substituent.

8. The method according to claim 1 , wherein, in a 1 H nuclear magnetic resonance spectroscopy, with the chemical shift of tetramethylsilane set as 0 ppm, the chemical shift δ of at least one hydrogen atom on the benzene ring is at least 8 ppm.

9. The method as claimed in claim 8 , wherein the spin-lattice relaxation time T 1 of the at least one hydrogen atom having the chemical shift of at least 8 ppm is not more than 5 s.

10. The method according to claim 8 , wherein the chemical shift of two hydrogen atoms on the benzene ring is at least 8 ppm, and the relaxation times of the two hydrogen atoms differ by at least 3 s.

11. The method according to claim 1 , wherein the compound is selected from the compounds having the formulae (3) to (8):

where the radicals R 2 and R 3 independently of one another are selected from the phenyl radical or benzyl radical shown in the respective formulae, H, CH 3 , and CH 2 —CH 3 , preferably from the phenyl radical or benzyl radical, H, and CH 3 .

12. The method according to claim 11 , wherein the compound is selected from the following compounds:

13. A method of identifying an analyte wherein the method comprises:
providing a standard compound for nuclear magnetic resonance spectroscopy, the standard compound comprised of the formula (9)

detecting the nuclear magnetic resonance of one of the atoms 1 H, 13 C, 15 N, 19 F, or 31 P; and
determining the analyte quantitatively.

Assignees

• Merck Patent Gmbh

Inventors

• Diehl Bernd Willi Karl-Heinz

Classifications

• G01R33/4633

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• G01N24/087

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• C07F9/36 Primary

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