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Enantioselective Complexation of Chiral Propylene Oxide by an Enantiopure Water-Soluble Cryptophane
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-9720-5429
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 10, 4178-4181 p.Article in journal (Refereed) Published
Abstract [en]

ECD and NMR experiments show that the complexation of propylene oxide (PrO) within the cavity of an enantiopure water-soluble cryptophane 1 in NaOH solution is enantioselective and that the (R)-PrO@PP-1 diastereomer is more stable than the (S)-PrO@PP-1 diastereomer with a free energy difference of 1.7 kJ/mol. This result has been confirmed to by molecular dynamics (MD) and ab initio calculations. The enantioselectivity is preserved in LiOH and KOH solutions even though the binding constants decrease, whereas PrO is not complexed in CsOH solution.

Place, publisher, year, edition, pages
2011. Vol. 76, no 10, 4178-4181 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-34213DOI: 10.1021/jo200519rISI: 000290465700068Scopus ID: 2-s2.0-79956158513OAI: oai:DiVA.org:kth-34213DiVA: diva2:423483
Funder
Swedish e‐Science Research Center
Note
QC 20110615Available from: 2011-06-15 Created: 2011-05-30 Last updated: 2017-12-11Bibliographically approved

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Ågren, Hans

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