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Cryptochirality in stereochemistry is a special case of chirality where due to the electronic properties of the chiral molecule its specific rotation is non-measurable. The term was introduced by K. Mislow in 1977.
Additional recommended knowledge
For example the alkane 5-ethyl-5-propylundecane or (n-butyl)ethyl(n-hexyl)(n-propyl)methane found in certain species of Phaseolus vulgaris has two enantiomeric forms without any observable optical rotation
It is still possible to distinguish between the two enantiomers by asymmetric synthesis with the (S)-alkane 3 in an autocatalytic system of the achiral aldehyde 1 and achiral Diisopropylzinc 2 to the chiral (R)-alcohol 4 with enantiomeric excess 94%:
For chiral induction to be possible C-H bonds in the alkane are believed to interact with the pi electrons of the aldehyde.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cryptochirality". A list of authors is available in Wikipedia.|