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Investigation of the behaviour of propylene oxide in water by 1H NMR measurements

As an electron donor solvent, propylene oxide (PO) forms a hydrogen bond with water in their binary mixture. The repulsion produced by the electrostatic field from the PO…HOH hydrogen bond forces the protons and methyl group of PO to bend away from the O group and results in the approach of these protons into the plane of the three‐membered ring. Consequently, they experience a stronger paramagnetic field from the ring current and their 1H resonances shift to a lower field. The changes of the HCH angle and HCCH dihedral angles of PO in water cause the geminal coupling constant and the vicinal cis coupling constant to decrease and the vicinal trans coupling constant to increase.