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  Encapsulation of alkyl and aryl derivatives of quaternary ammonium cations within cucurbit[n]uril (n = 6,7) and their inverted diastereomers: density functional investigations

Raja, I. A., Gobre, V., Pinjari, R. V., & Gejji, S. P. (2014). Encapsulation of alkyl and aryl derivatives of quaternary ammonium cations within cucurbit[n]uril (n = 6,7) and their inverted diastereomers: density functional investigations. Journal of Molecular Modeling, 20(3): 2138. doi:10.1007/s00894-014-2138-3.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0017-B520-0 Version Permalink: http://hdl.handle.net/21.11116/0000-0005-4A3E-4
Genre: Journal Article

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 Creators:
Raja, Ishita A.1, Author
Gobre, Vivekanand2, Author              
Pinjari, Rahul V.3, Author
Gejji, Shridhar P.1, Author
Affiliations:
1Department of Chemistry, University of Pune, Ganeshkhind, Pune, 411007, India , ou_persistent22              
2Theory, Fritz Haber Institute, Max Planck Society, ou_634547              
3School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded, 431606, India , ou_persistent22              

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Free keywords: Inclusion complex Electron density topography Inverted cucurbit[n]urils NMR chemical shifts Vibration frequency
 Abstract: Electronic structure, vibrational frequencies, and 1H chemical shifts of inclusion complexes between CB[n] (n = 6,7) or their inverted iCB[n] diastereomer hosts and quaternary diammonium viz., 1,6-hexyldiammonium (HDA) or p-xylyldiammonium (XYL) cationic guests are obtained from the density functional calculations. The interaction of CB[n] or iCB[n] with HDA (guest) conduce inclusion complexes in which the guest attains gauche conformation within the host cavity. The lowest energy XYL complexes of CB[6] or iCB[6] are comprised of one ammonium group orienting parallel to aromatic ring. The CB[7] or iCB[7] complexes of XYL on the other hand, reveal ammonium group(s) perpendicular to aromatic ring of the guest. The ureido C=O and N-H stretching vibrations on complexation engender frequency down-shift in the calculated spectra. This can be attributed to C-H---O and N-H---O interactions in the complex. The inverting of glycouril unit in iCB[n] renders a frequency shift (12 cm-1) for the C=O stretching in the opposite direction. Molecular electron density topography and natural bond orbital analyses have been used to explain the direction of frequency shifts. Calculated 1H NMR reveal that guest protons within the host cavity not participating in hydrogen bonding interactions, exhibit shielded signals compared to isolated XYL or HDA. Likewise the inverted protons in the iCB[6]-XYL complex led to up-field signals in calculated 1H NMR as a result of C-H---π interactions.

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Language(s): eng - English
 Dates: 2014-022014-03
 Publication Status: Published in print
 Pages: 17
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1007/s00894-014-2138-3
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Title: Journal of Molecular Modeling
  Other : J. Mol. Model.
Source Genre: Journal
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Publ. Info: Berlin : Springer
Pages: - Volume / Issue: 20 (3) Sequence Number: 2138 Start / End Page: - Identifier: ISSN: 1610-2940
CoNE: https://pure.mpg.de/cone/journals/resource/954925573936