US 12,292,493 B2
Method for heteronuclear quantitative determination by NMR spectroscopy, reference substances therefor and method for determining the degree of deuteration of a deuterated compound
Bernd Willi Karl-Heinz Diehl, Cologne (DE)
Assigned to Bruker Biospin GmbH, Rheinstetten (DE)
Appl. No. 16/979,137
Filed by Bruker Biospin GmbH, Rheinstetten (DE)
PCT Filed Mar. 6, 2019, PCT No. PCT/EP2019/055520
§ 371(c)(1), (2) Date Sep. 8, 2020,
PCT Pub. No. WO2019/170717, PCT Pub. Date Sep. 12, 2019.
Claims priority of application No. 10 2018 203 434.6 (DE), filed on Mar. 7, 2018.
Prior Publication US 2020/0400766 A1, Dec. 24, 2020
Int. Cl. G01R 33/46 (2006.01); G01R 35/00 (2006.01)
CPC G01R 33/4625 (2013.01) [G01R 35/005 (2013.01)] 2 Claims
OG exemplary drawing
 
1. A method for determining the degree of deuteration of a first deuterated compound, the method comprises the steps:
preparing a mixture of the first deuterated compound and a second deuterated compound whose degree of deuteration is known, so that both deuterated compounds are dissolved;
generating a 1H NMR spectrum from the mixture and determining the integrals of at least one peak of each of the two deuterated compounds;
generating a 2H NMR spectrum from the mixture and determining the integrals of the same peaks;
calculating the degree of deuteration of the first deuterated compound using the determined integral values and the known degree of deuteration of the second deuterated compound by means of equation (4)
{D}Vb1=100−({H}Vb2×(IntHVb2/IntDVb2)/(IntHVb1/IntDVb1)  (4)
wherein:
{D}Vb1=degree of deuteration of the first deuterated compound,
{H}Vb2=degree of protonation of the second deuterated compound,
IntHVb1=Integral of a peak of the first deuterated compound in the 1H NMR spectrum,
IntDVb1=Integral of the same peak of the first deuterated compound in the 2H NMR spectrum,
IntHVb2=Integral of a peak of the second deuterated compound in the 1H NMR spectrum, and
IntDVb2=Integral of the same peak of the second deuterated compound in the 2H NMR spectrum.