A study of hydrogen bonds in p-substituted calix[4]-and calix[6]arenes by ab initio and electron density functional methods View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2010-12

AUTHORS

A. N. Novikov, Yu. E. Shapiro

ABSTRACT

RHF/3-21G and B3LYP/3-21G methods are used to calculate the hydrogen bond energies in calix[4]-, calix[6]-, p-fluorocalix[4]-, p-fluorocalix[6]-, p-chlorocalix[4]-, p-chlorocalix[6]-, p-bromocalix[4]-, pbromocalix[6]-, p-iodocalix[4]-, p-iodocalix[6]-arenes and a number of other p-substituted calix[4]- and calix[6]arenes (R = Me, OMe, NO2, Ac, NH2, CN, N2+). The calculations along with the structural data give evidence of the cooperative effect of hydrogen bonding. Multiple correlation (p ≥ 0.9) between the pairs of Hammett substituent constants and the calculated values of hydrogen bond energies in the corresponding p-substituted calixarenes is found. It is predicted that in the presence of weak bases and in aprotic solvents as well as in the gas phase, the nucleophilic substitution reaction involving p-halogen calix[6]arenes should proceed through diastereomeric transition states. More... »

PAGES

1024-1033

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10947-010-0159-z

DOI

http://dx.doi.org/10.1007/s10947-010-0159-z

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https://app.dimensions.ai/details/publication/pub.1027468221


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