Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2006-11

AUTHORS

A. N. Novikov, V. A. Bacherikov, Yu. E. Shapiro, A. I. Gren

ABSTRACT

The cone conformation of C4 symmetry is shown by the Hartree-Fock method (3-21G basis) to be the predominant conformer of calix[4]arene; the compressed cone of C2 symmetry is the major conformer of calix[6]arene. Using quantum chemical methods we calculated hydrogen bond cleavage energies for calix[4]-(ab initio and density functional methods) and calix[6]arene (ab initio), and also for the complex of calix[4]arene with carbon disulfide. These energies along with structural data point to the cooperative effect of hydrogen bonds. The results of these studies provided an explanation to the greater conformational lability of calix[6]arene compared with calix[4]arene molecules. It is also predicted that the nucleophilic substitution reaction involving calix[6]arene in the presence of weak bases and in aprotic solvents, as well as in the gas phase, will occur via diastereomeric transition states. More... »

PAGES

1003-1015

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10947-006-0419-0

DOI

http://dx.doi.org/10.1007/s10947-006-0419-0

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1025017234


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