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Conformational Effects Induced by Guest Encapsulation in an Enantiopure Water-Soluble Cryptophane
KTH, School of Biotechnology (BIO), Theoretical Chemistry (closed 20110512).ORCID iD: 0000-0002-9720-5429
KTH, School of Biotechnology (BIO), Theoretical Chemistry (closed 20110512).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 5, 1372-1383 p.Article in journal (Refereed) Published
Abstract [en]

A new water-soluble cryptophane 1 derivative (penta-hydroxyl cryptophane-A) has been synthesized from cryptophanol-A and the chiroptical properties of its two enantiomers M M-1 and P P-1 have been studied by polarimetry, electronic circular dichroism (ECD), and vibrational circular dichroism (VCD). Cryptophane 1 shows specific circular dichroism responses upon complexation that depend on the size of the guest and on the nature of the counterion (Li+, Na+, K+, Cs+) present in the solution. In LiOH and NaOH solutions, chiroptical changes induced by the encapsulation of guests and by the presence of cations in the vicinity of hosts can be interpreted from molecular dynamics (MD) and ab initio calculations by subtle conformational changes of the bridges. In KOH solution, the exchange dynamics is dependent on the size of the guest molecules, whereas in CsOH solution no encapsulation effect is observed whatever the size of the guest molecule. This last behavior comes from the fact that host 1 exhibits a very high affinity for cesium cations.

Place, publisher, year, edition, pages
2011. Vol. 76, no 5, 1372-1383 p.
Keyword [en]
VIBRATIONAL CIRCULAR-DICHROISM; ATOM FORCE-FIELD; CHIROPTICAL PROPERTIES; COMPLEXATION DYNAMICS; HYPERPOLARIZED XENON; MAGNETIC-RESONANCE; INCLUSION COMPLEX; ORGANIC SOLUTION; NMR; MOLECULES
National Category
Theoretical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-31863DOI: 10.1021/jo102350gISI: 000287636200017Scopus ID: 2-s2.0-79952119914OAI: oai:DiVA.org:kth-31863DiVA: diva2:408330
Funder
Swedish e‐Science Research Center
Note
QC 20110404Available from: 2011-04-04 Created: 2011-03-28 Last updated: 2017-12-11Bibliographically approved

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Ågren, Hans

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