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. 2022 Feb 8;12(8):4692–4696. doi: 10.1039/d2ra00428c

Measurements of 1H ΔΔδ values of racemic chiral diols in the presence of boric acid D by 1H NMR (400 MHz) in CDCl3 at 25 °Ca.

Entry Chiral diols Spectrab ΔΔδc (ppm)
1 graphic file with name d2ra00428c-u1.jpg graphic file with name d2ra00428c-u2.jpg 0.39
2 graphic file with name d2ra00428c-u3.jpg graphic file with name d2ra00428c-u4.jpg 0.18
3 graphic file with name d2ra00428c-u5.jpg graphic file with name d2ra00428c-u6.jpg 0.10
4 graphic file with name d2ra00428c-u7.jpg graphic file with name d2ra00428c-u8.jpg 0.11
5 graphic file with name d2ra00428c-u9.jpg graphic file with name d2ra00428c-u10.jpg 0.11
6 graphic file with name d2ra00428c-u11.jpg graphic file with name d2ra00428c-u12.jpg 0.23
7 graphic file with name d2ra00428c-u13.jpg graphic file with name d2ra00428c-u14.jpg 0.27
8 graphic file with name d2ra00428c-u15.jpg graphic file with name d2ra00428c-u16.jpg 0.18
9 graphic file with name d2ra00428c-u17.jpg graphic file with name d2ra00428c-u18.jpg 0.11
10 graphic file with name d2ra00428c-u19.jpg graphic file with name d2ra00428c-u20.jpg 0.17
11 graphic file with name d2ra00428c-u21.jpg graphic file with name d2ra00428c-u22.jpg 0.08
12 graphic file with name d2ra00428c-u23.jpg graphic file with name d2ra00428c-u24.jpg 0.06
a

All samples were prepared by mixing boric acid D and chiral diols in NMR tubes (10 mM of the chiral diols and 30 mM of boric acid D in 0.6 mL of CDCl3). 1H NMR were collected on a Bruker Avance 400 MHz. Spectrometer at 25 °C.

b

The configurations were determined by comparing with spectra of nonracemic sample of known configurations; the red and blue lines represent the S and R enantiomers of analytes, respectively (entry 1 red is (S,S) and blue is (R,R), entry 8 red is (−) and blue is (+)).

c

ΔΔδ values of the proton HA of the derivatives.