Inherently chiral calixarene with XXYZ substitution pattern.
In chemistry, inherent chirality is a property of asymmetry in molecules arising, not from a stereogenic or chiral center, but from a twisting of the molecule in 3-D space. The term was first coined by Volker Boehmer in a 1994 review, to describe the chirality of calixarenes arising from their non-planar structure in 3-D space.
This phenomenon was described as resulting from "the absence of a place of symmetry or an inversion center in the molecule as a whole".[1] Boehmer further explains this phenomenon by suggesting that if an inherently chiral calixarene macrocycle were opened up it would produce an "achiral linear molecule".[1] There are two commonly used notations to describe a molecules inherent chirality: cR/cS (arising from the notation used for classically chiral compounds, with c denoting curvature) and P/M.[2][irrelevant citation] Inherently chiral molecules, like their classically chiral counterparts, can be used in chiral host–guest chemistry, enantioselective synthesis, and other applications.[3] There are naturally occurring inherently chiral molecules as well. Retinal, a chromophore in rhodopsin. exists in solution as a racemic pair of enantiomers due to the curvature of an achiral polyene chain.[4]
^ abDalla Cort, Antonella; Mandolini, Luigi; Pasquini, Chiara; Schiaffino, Luca (2004-10-01). ""Inherent chirality" and curvature". New J. Chem. 28 (10): 1198–1199. doi:10.1039/b404388j. ISSN 1369-9261.
^Böhmer, Volker; Kraft, Dagmar; Tabatabai, Moniralsadat (1994-03-01). "Inherently chiral calixarenes". Journal of Inclusion Phenomena and Molecular Recognition in Chemistry. 19 (1–4): 17–39. doi:10.1007/bf00708972. ISSN 0923-0750. S2CID 198509371.
^Shirakawa, Seiji; Moriyama, Akihiro; Shimizu, Shoichi (2007-08-01). "Design of a Novel Inherently Chiral Calix[4]arene for Chiral Molecular Recognition". Organic Letters. 9 (16): 3117–3119. doi:10.1021/ol071249p. ISSN 1523-7060. PMID 17616144.
^Szumna, Agnieszka (2010-10-19). "Inherently chiral concave molecules—from synthesis to applications". Chemical Society Reviews. 39 (11): 4274–85. doi:10.1039/b919527k. ISSN 1460-4744. PMID 20882239.
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