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

作者：Peerannawar Swarada R; Rao Soniya S; Gejji Shridhar P^*

来源：Journal of Molecular Modeling, 2014, 20(1): 2073.

DOI：10.1007/s00894-014-2073-3

• Cucurbit[n]uril
• 2-Naphthalenecarbonitrile (2-NpCN)
• Density functional theory

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 H-1 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.

• 出版日期2014-1