TY - JOUR
T1 - A selective acetate anion binding receptor
T2 - Participation via cationic CH3 donors
AU - Pandian, Thiravidamani Senthil
AU - Srinivasadesikan, Venkatesan
AU - Lin, Ming-Chang
AU - Kang, Jongmin
PY - 2015/10/28
Y1 - 2015/10/28
N2 - A novel receptor 1, which has only C-H hydrogen bonds as recognition element has been designed and synthesized. The receptor 1 utilizes cationic CH3 in 2-methyl benzimidazole and naphthalene benzylic C-H as hydrogen bonding donor. The binding cavity formed in receptor 1 prefers to accommodate small negatively charged atom such as oxygen. Therefore, acetate and nitrite show strong affinity for receptor 1 in acetonitrile due to negatively charged oxygen in them. In addition, the order of binding affinity for halides are Br->Cl->I-. These results reflect the size and basicities of halides. Further, 1H NMR titration of halide clearly indicates the anion-π interaction. The experimental data from UV-vis, fluorescence and 1H NMR titration are consistent with DFT results.
AB - A novel receptor 1, which has only C-H hydrogen bonds as recognition element has been designed and synthesized. The receptor 1 utilizes cationic CH3 in 2-methyl benzimidazole and naphthalene benzylic C-H as hydrogen bonding donor. The binding cavity formed in receptor 1 prefers to accommodate small negatively charged atom such as oxygen. Therefore, acetate and nitrite show strong affinity for receptor 1 in acetonitrile due to negatively charged oxygen in them. In addition, the order of binding affinity for halides are Br->Cl->I-. These results reflect the size and basicities of halides. Further, 1H NMR titration of halide clearly indicates the anion-π interaction. The experimental data from UV-vis, fluorescence and 1H NMR titration are consistent with DFT results.
KW - Acetate
KW - Anion receptor
KW - Anion-π interaction
KW - C-H hydrogen bonds
KW - Nitrite
UR - http://www.scopus.com/inward/record.url?scp=84942373658&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2015.08.015
DO - 10.1016/j.tet.2015.08.015
M3 - Article
AN - SCOPUS:84942373658
SN - 0040-4020
VL - 71
SP - 8350
EP - 8356
JO - Tetrahedron
JF - Tetrahedron
IS - 43
ER -