A selective acetate anion binding receptor: Participation via cationic CH3 donors

Thiravidamani Senthil Pandian; Venkatesan Srinivasadesikan; Ming-Chang Lin; Jongmin Kang

doi:10.1016/j.tet.2015.08.015

A selective acetate anion binding receptor: Participation via cationic CH₃ donors

Thiravidamani Senthil Pandian, Venkatesan Srinivasadesikan, Ming-Chang Lin, Jongmin Kang^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8350-8356
Number of pages	7
Journal	Tetrahedron
Volume	71
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2015.08.015
State	Published - 28 Oct 2015

Keywords

Acetate
Anion receptor
Anion-π interaction
C-H hydrogen bonds
Nitrite

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10.1016/j.tet.2015.08.015

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title = "A selective acetate anion binding receptor: Participation via cationic CH3 donors",

abstract = "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.",

keywords = "Acetate, Anion receptor, Anion-π interaction, C-H hydrogen bonds, Nitrite",

author = "Pandian, {Thiravidamani Senthil} and Venkatesan Srinivasadesikan and Ming-Chang Lin and Jongmin Kang",

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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

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U2 - 10.1016/j.tet.2015.08.015

DO - 10.1016/j.tet.2015.08.015

M3 - Article

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SN - 0040-4020

VL - 71

SP - 8350

EP - 8356

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

A selective acetate anion binding receptor: Participation via cationic CH₃ donors

Abstract

Keywords

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