Propanediurea-Based Molecular Clips Bind Halide Anions: An
Insight into the Mechanism of Cucurbituril Formation

J 2016

Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation

LÍZAL, Tomáš, Lukáš USTRNUL, Marek NEČAS and Vladimír ŠINDELÁŘ

Basic information

Original name

Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation

Authors

LÍZAL, Tomáš (203 Czech Republic, belonging to the institution), Lukáš USTRNUL (203 Czech Republic, belonging to the institution), Marek NEČAS (203 Czech Republic, belonging to the institution) and Vladimír ŠINDELÁŘ (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2016, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.849

RIV identification code

RIV/00216224:14310/16:00088594

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.6b01602

UT WoS

000385054300023

Keywords (in Czech)

propandimočovina; molekulová klipsy; vázání aniontů; příprava cucurbiturilů

Keywords in English

BRIDGED GLYCOLURIL DIMERS; DIASTEREOSELECTIVE FORMATION; HIGH-AFFINITY; HOST; DERIVATIVES; WATER; ISOMERIZATION; RECOGNITION; SOLUBILITY; MACROCYCLE

Abstract

V originále

The synthesis and supramolecular properties of the first methylene-bridged propanediurea-based dimers are described. These dimers, bearing an aromatic sidewall, have the shape of molecular clips. Unlike glycoluril-based dimers, these clips neither dimerize nor accept any organic guests, due to their small cavities. Both propanediurea- and glycoluril-based dimers bind halide anions on the convex side of the molecules, even in highly polar organic solvents. This observation brings new insights into the mechanism of cucurbituril formation.

Links

GA13-15576S, research and development project

Name: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Czech Science Foundation

LM2011028, research and development project

Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

Investor: Ministry of Education, Youth and Sports of the CR

LM2015043, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

LÍZAL, Tomáš, Lukáš USTRNUL, Marek NEČAS and Vladimír ŠINDELÁŘ. Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation. Journal of Organic Chemistry. WASHINGTON: AMER CHEMICAL SOC, 2016, vol. 81, No 19, p. 8906-8910. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b01602.

@article{1369146,
   author = {Lízal, Tomáš and Ustrnul, Lukáš and Nečas, Marek and Šindelář, Vladimír},
   article_location = {WASHINGTON},
   article_number = {19},
   doi = {http://dx.doi.org/10.1021/acs.joc.6b01602},
   keywords = {BRIDGED GLYCOLURIL DIMERS; DIASTEREOSELECTIVE FORMATION; HIGH-AFFINITY; HOST; DERIVATIVES; WATER; ISOMERIZATION; RECOGNITION; SOLUBILITY; MACROCYCLE},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01602},
   volume = {81},
   year = {2016}
}

TY  - JOUR
ID  - 1369146
AU  - Lízal, Tomáš - Ustrnul, Lukáš - Nečas, Marek - Šindelář, Vladimír
PY  - 2016
TI  - Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation
JF  - Journal of Organic Chemistry
VL  - 81
IS  - 19
SP  - 8906-8910
EP  - 8906-8910
PB  - AMER CHEMICAL SOC
SN  - 00223263
KW  - BRIDGED GLYCOLURIL DIMERS
KW  - DIASTEREOSELECTIVE FORMATION
KW  - HIGH-AFFINITY
KW  - HOST
KW  - DERIVATIVES
KW  - WATER
KW  - ISOMERIZATION
KW  - RECOGNITION
KW  - SOLUBILITY
KW  - MACROCYCLE
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01602
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01602
N2  - The synthesis and supramolecular properties of the first methylene-bridged propanediurea-based dimers are described. These dimers, bearing an aromatic sidewall, have the shape of molecular clips. Unlike glycoluril-based dimers, these clips neither dimerize nor accept any organic guests, due to their small cavities. Both propanediurea- and glycoluril-based dimers bind halide anions on the convex side of the molecules, even in highly polar organic solvents. This observation brings new insights into the mechanism of cucurbituril formation.
ER  -

LÍZAL, Tomáš, Lukáš USTRNUL, Marek NEČAS and Vladimír ŠINDELÁŘ. Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, 2016, vol.~81, No~19, p.~8906-8910. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b01602.

Detailed Information on Publication Record