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Halogenated isophthalamides and dipicolineamides: the role of the halogen substituents in the anion binding properties

Halogenated isophthalamides and dipicolineamides: the role of the halogen substituents in the anion binding properties
Halogenated isophthalamides and dipicolineamides: the role of the halogen substituents in the anion binding properties

A novel family of amide-based receptors is herein described. Specifically, the role of the halogen substituents at the aryl moieties in the anion binding properties of a series of halogenated isophthalamides and dipicolineamides (L1-L6) was investigated both in solution and in the solid state in order to evaluate the incidence of all possible different and combined weak host-guest interactions. Only L5 and L6 bearing pentafluorophenyl rings as substituents have some affinities for the set of anions studied. In particular, in the case of L5 an interesting behaviour with the formation of a non-symmetric adduct with benzoate and dihydrogen phosphate was hypothesised by 1H- A nd 19F-NMR spectroscopy studies in solution and confirmed by theoretical calculation. The study of the crystal structures of the receptors demonstrated that the steric hindrance determined by the halogen substituents in the receptor molecules influences the accessibility of the anions to the isophthalamide or dipicoline amide NH moieties, thus modulating the affinity for the anion guests.

1477-9226
9231-9238
Picci, Giacomo
c95864bc-877f-4cea-a761-276ea5a10c6a
Bazzicalupi, Carla
6b1e1f3f-eaa7-4019-82bb-9d3410215c39
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gratteri, Paola
03964e4f-0fd4-4e4a-96b0-fa99cbdfa057
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Montis, Riccardo
2d2d60eb-b455-414a-80d8-d5a58002bd92
Murgia, Sergio
51153288-1749-4337-8536-9f5e7d8920a9
Nocentini, Alessio
12afe52e-623b-4307-8ff9-a9799e0f25a2
Orton, James B.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Picci, Giacomo
c95864bc-877f-4cea-a761-276ea5a10c6a
Bazzicalupi, Carla
6b1e1f3f-eaa7-4019-82bb-9d3410215c39
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gratteri, Paola
03964e4f-0fd4-4e4a-96b0-fa99cbdfa057
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Montis, Riccardo
2d2d60eb-b455-414a-80d8-d5a58002bd92
Murgia, Sergio
51153288-1749-4337-8536-9f5e7d8920a9
Nocentini, Alessio
12afe52e-623b-4307-8ff9-a9799e0f25a2
Orton, James B.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0

Picci, Giacomo, Bazzicalupi, Carla, Coles, Simon J., Gratteri, Paola, Isaia, Francesco, Lippolis, Vito, Montis, Riccardo, Murgia, Sergio, Nocentini, Alessio, Orton, James B. and Caltagirone, Claudia (2020) Halogenated isophthalamides and dipicolineamides: the role of the halogen substituents in the anion binding properties. Dalton Transactions, 49 (27), 9231-9238. (doi:10.1039/d0dt01492c).

Record type: Article

Abstract

A novel family of amide-based receptors is herein described. Specifically, the role of the halogen substituents at the aryl moieties in the anion binding properties of a series of halogenated isophthalamides and dipicolineamides (L1-L6) was investigated both in solution and in the solid state in order to evaluate the incidence of all possible different and combined weak host-guest interactions. Only L5 and L6 bearing pentafluorophenyl rings as substituents have some affinities for the set of anions studied. In particular, in the case of L5 an interesting behaviour with the formation of a non-symmetric adduct with benzoate and dihydrogen phosphate was hypothesised by 1H- A nd 19F-NMR spectroscopy studies in solution and confirmed by theoretical calculation. The study of the crystal structures of the receptors demonstrated that the steric hindrance determined by the halogen substituents in the receptor molecules influences the accessibility of the anions to the isophthalamide or dipicoline amide NH moieties, thus modulating the affinity for the anion guests.

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Accepted/In Press date: 18 May 2020
e-pub ahead of print date: 19 May 2020
Published date: 21 July 2020

Identifiers

Local EPrints ID: 443249
URI: http://eprints.soton.ac.uk/id/eprint/443249
ISSN: 1477-9226
PURE UUID: 5333c621-7df4-4332-b647-ef0e6bcba9ac
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 19 Aug 2020 16:31
Last modified: 26 Nov 2021 05:59

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Contributors

Author: Giacomo Picci
Author: Carla Bazzicalupi
Author: Simon J. Coles ORCID iD
Author: Paola Gratteri
Author: Francesco Isaia
Author: Vito Lippolis
Author: Riccardo Montis
Author: Sergio Murgia
Author: Alessio Nocentini
Author: James B. Orton
Author: Claudia Caltagirone

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