Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition

M. Angeles Garciía; M. Angeles Farrán; Dolores Santa María; Rosa M. Claramunt; M. Carmen Torralba; M. Rosario Torres; Carlors Jaime; José Elguero

doi:https://doi.org/10.3390/molecules20069862

Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition

M. Angeles Garciía, M. Angeles Farrán, Dolores Santa María, Rosa M. Claramunt, M. Carmen Torralba, M. Rosario Torres, Carlors Jaime, José Elguero

Department of Chemistry

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

3 Citations (Scopus)

Abstract

The association constants of the complexes formed by two hosts containing pyrrole, amide and azine (pyridine and 1,8-naphthyridine) groups and six guests, all monoanions (Cl^-, CH3CO2^-, NO3^-, H2PO4^-, BF4^-, PF6^-), have been determined using NMR titrations. The X-ray crystal structure of the host N²,N⁵-bis(6-methylpyridin-2-yl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide (1) has been solved (P21/c monoclinic space group). B3LYP/6-31G(d,p) and calculations were carried out in an attempt to rationalize the trends observed in the experimental association constants.

Original language	English
Pages (from-to)	9862-9878
Journal	Molecules
Volume	20
Issue number	6
DOIs	https://doi.org/10.3390/molecules20069862
Publication status	Published - 1 Jun 2015

Keywords

Anion binding
Association constants
B3LYP/6-31G(d,p) calculations
Nmr titrations
X-ray structures

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title = "Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition",

abstract = "The association constants of the complexes formed by two hosts containing pyrrole, amide and azine (pyridine and 1,8-naphthyridine) groups and six guests, all monoanions (Cl-, CH3CO2-, NO3-, H2PO4-, BF4-, PF6-), have been determined using NMR titrations. The X-ray crystal structure of the host N2,N5-bis(6-methylpyridin-2-yl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide (1) has been solved (P21/c monoclinic space group). B3LYP/6-31G(d,p) and calculations were carried out in an attempt to rationalize the trends observed in the experimental association constants.",

keywords = "Anion binding, Association constants, B3LYP/6-31G(d,p) calculations, Nmr titrations, X-ray structures",

author = "Garci{\'i}a, {M. Angeles} and Farr{\'a}n, {M. Angeles} and Mar{\'i}a, {Dolores Santa} and Claramunt, {Rosa M.} and Torralba, {M. Carmen} and Torres, {M. Rosario} and Carlors Jaime and Jos{\'e} Elguero",

year = "2015",

month = jun,

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doi = "https://doi.org/10.3390/molecules20069862",

language = "English",

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T1 - Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition

AU - Garciía, M. Angeles

AU - Farrán, M. Angeles

AU - María, Dolores Santa

AU - Claramunt, Rosa M.

AU - Torralba, M. Carmen

AU - Torres, M. Rosario

AU - Jaime, Carlors

AU - Elguero, José

PY - 2015/6/1

Y1 - 2015/6/1

N2 - The association constants of the complexes formed by two hosts containing pyrrole, amide and azine (pyridine and 1,8-naphthyridine) groups and six guests, all monoanions (Cl-, CH3CO2-, NO3-, H2PO4-, BF4-, PF6-), have been determined using NMR titrations. The X-ray crystal structure of the host N2,N5-bis(6-methylpyridin-2-yl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide (1) has been solved (P21/c monoclinic space group). B3LYP/6-31G(d,p) and calculations were carried out in an attempt to rationalize the trends observed in the experimental association constants.

AB - The association constants of the complexes formed by two hosts containing pyrrole, amide and azine (pyridine and 1,8-naphthyridine) groups and six guests, all monoanions (Cl-, CH3CO2-, NO3-, H2PO4-, BF4-, PF6-), have been determined using NMR titrations. The X-ray crystal structure of the host N2,N5-bis(6-methylpyridin-2-yl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide (1) has been solved (P21/c monoclinic space group). B3LYP/6-31G(d,p) and calculations were carried out in an attempt to rationalize the trends observed in the experimental association constants.

KW - Anion binding

KW - Association constants

KW - B3LYP/6-31G(d,p) calculations

KW - Nmr titrations

KW - X-ray structures

U2 - https://doi.org/10.3390/molecules20069862

DO - https://doi.org/10.3390/molecules20069862

M3 - Article

SN - 1420-3049

VL - 20

SP - 9862

EP - 9878

JO - Molecules

JF - Molecules

IS - 6

ER -

Pyrrole-pyridine and pyrrole-naphthyridine hosts for anion recognition

Abstract

Keywords

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