Suppose there is a phosphate group with P attached to 4 groups-
-O-R, -O-R', -O, =O (Last two differs by the bond type: single and double bond)
The P is sp3 hybridised and would be chiral if all 4 groups attached to it are different. Are -O (single bond) and =O (double bond) considered to be different groups by virtue of their difference in bond type?
Yes, it is possible if the oxygen atoms are from different isotopes, 16O and 17O, for example. If both atoms are from the same isotope, then they are prochiral, i.e. they will be distinguishable in a chiral environment (medium or chiral solvate or cation)
Thank you for your answer Andrei Rogoza .
The O atoms in question are from same isotope, but only differ by their bond type to the central atom P. Does having different bond types lead to chirality in this case?
In this case, there would be a resonance between the two-oxygen atoms attached to the phosphate group which leads to the presence of a plane of symmetry, and due to this plane of symmetry, the molecule should be achiral.
For surety, I would suggest you synthesize such molecules and test chiral polarity.
As Andrei Rogoza stated above, phosphate diesters are prochiral at the P atom. If, however, one of the oxygen atoms is replaced by sulfur or by an alkyl group, the resulting compounds, phosphorothioate diesters and alkylphosphonate diesters, respectively, are chiral i.e. they exist as two enantiomers, Rp and Sp.
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