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Density functional investigations on 2-naphthalenecarbonitrile dimerization within cucurbit[8]uril cavitand

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Abstract

Dimerization of 2-naphthalenecarbonitrile (2-NpCN) mediated by cucurbit[8]uril (CB[8]) has been investigated employing the density functional theory. Different structures of 2-NpCN dimers were generated by combining monomers in anti-head-to-head (A), anti-head-to-tail (B) and syn-head-to-tail (C) fashion. All these dimeric structures possess rigid cube-like architecture. On confinement within the CB[8] dimer A turns out to be the lowest energy structure. Calculated 1H NMR spectra revealed that the 2-NpCN dimer exhibits large shielding for aromatic protons consistent with the experiment. The protons attached to cubane moiety on the other hand, led to down-field signals. Dimerization mediated with CB[8] cavitand is further accompanied by the frequency up-shift (blue shift) of methylene stretching vibration in its infrared spectra.

2-naphthalenecarbonitrile

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Acknowledgments

S. P. G. is grateful to the University Grants Commission (UGC), New Delhi, India [Research Project F34-370/2008(SR)].

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Authors and Affiliations

  1. Department of Chemistry, University of Pune, Pune, 411 007, India

    Swarada R. Peerannawar, Soniya S. Rao & Shridhar P. Gejji

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  1. Swarada R. Peerannawar
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  2. Soniya S. Rao
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  3. Shridhar P. Gejji
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Correspondence to Shridhar P. Gejji.

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Peerannawar, S.R., Rao, S.S. & Gejji, S.P. Density functional investigations on 2-naphthalenecarbonitrile dimerization within cucurbit[8]uril cavitand. J Mol Model 20, 2073 (2014). https://doi.org/10.1007/s00894-014-2073-3

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  • DOI: https://doi.org/10.1007/s00894-014-2073-3

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