Non-symmetric substituted ureas locked in an (E,Z) conformation: An unusual anion binding via supramolecular assembly

Martina Olivari; Claudia Caltagirone; Alessandra Garau; Francesco Isaia; Mark E. Light; Vito Lippolis; Riccardo Montis; Mariano Andrea Scorciapino

doi:10.1039/c2nj40877e

Non-symmetric substituted ureas locked in an (E,Z) conformation: An unusual anion binding via supramolecular assembly

Martina Olivari, Claudia Caltagirone^*, Alessandra Garau, Francesco Isaia, Mark E. Light, Vito Lippolis, Riccardo Montis, Mariano Andrea Scorciapino

^*Corresponding author for this work

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

Abstract

Two new asymmetric ureidic receptors L¹ (1-(1H-indol-7-yl)-3- (quinolin-2-yl)urea) and L² (1-(quinolin-2-yl)-3-(quinolin-8-yl)urea) have been synthesised and their affinity towards different anions tested in DMSO-d₆. L¹ adopts both in solution and in the solid state an (E,Z) conformation. A moderate affinity for acetate has been observed for L¹ while no interaction has been observed for L². The different behaviour has been ascribed to the presence/absence of the indole group. In the case of L¹ the indole group causes the formation of a peculiar supramolecular architecture with two molecules of the receptor binding the anions in the (E,Z) conformation via H-bonds. L² also adopts an (E,Z) conformation in the solid state. However, the absence of the indole group in L² hampers the formation of the supramolecular assembly with the participation of anionic species.

Original language	English
Pages (from-to)	663-669
Number of pages	7
Journal	New Journal of Chemistry
Volume	37
Issue number	3
DOIs	https://doi.org/10.1039/c2nj40877e
Publication status	Published - 1 Mar 2013

Access to Document

10.1039/c2nj40877e

Cite this

@article{3ec759660d2143f2acc53af0b646f218,

title = "Non-symmetric substituted ureas locked in an (E,Z) conformation: An unusual anion binding via supramolecular assembly",

abstract = "Two new asymmetric ureidic receptors L1 (1-(1H-indol-7-yl)-3- (quinolin-2-yl)urea) and L2 (1-(quinolin-2-yl)-3-(quinolin-8-yl)urea) have been synthesised and their affinity towards different anions tested in DMSO-d6. L1 adopts both in solution and in the solid state an (E,Z) conformation. A moderate affinity for acetate has been observed for L1 while no interaction has been observed for L2. The different behaviour has been ascribed to the presence/absence of the indole group. In the case of L1 the indole group causes the formation of a peculiar supramolecular architecture with two molecules of the receptor binding the anions in the (E,Z) conformation via H-bonds. L2 also adopts an (E,Z) conformation in the solid state. However, the absence of the indole group in L2 hampers the formation of the supramolecular assembly with the participation of anionic species.",

author = "Martina Olivari and Claudia Caltagirone and Alessandra Garau and Francesco Isaia and Light, {Mark E.} and Vito Lippolis and Riccardo Montis and Scorciapino, {Mariano Andrea}",

year = "2013",

month = mar,

day = "1",

doi = "10.1039/c2nj40877e",

language = "English",

volume = "37",

pages = "663--669",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "3",

}

TY - JOUR

T1 - Non-symmetric substituted ureas locked in an (E,Z) conformation

T2 - An unusual anion binding via supramolecular assembly

AU - Olivari, Martina

AU - Caltagirone, Claudia

AU - Garau, Alessandra

AU - Isaia, Francesco

AU - Light, Mark E.

AU - Lippolis, Vito

AU - Montis, Riccardo

AU - Scorciapino, Mariano Andrea

PY - 2013/3/1

Y1 - 2013/3/1

N2 - Two new asymmetric ureidic receptors L1 (1-(1H-indol-7-yl)-3- (quinolin-2-yl)urea) and L2 (1-(quinolin-2-yl)-3-(quinolin-8-yl)urea) have been synthesised and their affinity towards different anions tested in DMSO-d6. L1 adopts both in solution and in the solid state an (E,Z) conformation. A moderate affinity for acetate has been observed for L1 while no interaction has been observed for L2. The different behaviour has been ascribed to the presence/absence of the indole group. In the case of L1 the indole group causes the formation of a peculiar supramolecular architecture with two molecules of the receptor binding the anions in the (E,Z) conformation via H-bonds. L2 also adopts an (E,Z) conformation in the solid state. However, the absence of the indole group in L2 hampers the formation of the supramolecular assembly with the participation of anionic species.

AB - Two new asymmetric ureidic receptors L1 (1-(1H-indol-7-yl)-3- (quinolin-2-yl)urea) and L2 (1-(quinolin-2-yl)-3-(quinolin-8-yl)urea) have been synthesised and their affinity towards different anions tested in DMSO-d6. L1 adopts both in solution and in the solid state an (E,Z) conformation. A moderate affinity for acetate has been observed for L1 while no interaction has been observed for L2. The different behaviour has been ascribed to the presence/absence of the indole group. In the case of L1 the indole group causes the formation of a peculiar supramolecular architecture with two molecules of the receptor binding the anions in the (E,Z) conformation via H-bonds. L2 also adopts an (E,Z) conformation in the solid state. However, the absence of the indole group in L2 hampers the formation of the supramolecular assembly with the participation of anionic species.

UR - http://www.scopus.com/inward/record.url?scp=84874062174&partnerID=8YFLogxK

U2 - 10.1039/c2nj40877e

DO - 10.1039/c2nj40877e

M3 - Article

AN - SCOPUS:84874062174

SN - 1144-0546

VL - 37

SP - 663

EP - 669

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 3

ER -

Non-symmetric substituted ureas locked in an (E,Z) conformation: An unusual anion binding via supramolecular assembly

Abstract

Access to Document

Other files and links

Fingerprint

Cite this