Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site

Iago Neira; Marcos D. García; Carlos Peinador; Angel E. Kaifer

doi:10.1021/acs.joc.8b02993

Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site

Iago Neira, Marcos D. García, Carlos Peinador, Angel E. Kaifer

Chemistry

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

11 Scopus citations

Abstract

A series of bis(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit[7]uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of complex association/dissociation is strongly affected. The relative position (meta, para) of the carboxylate group in relation to the pyridinium nitrogen also exerts a considerable effect on the binding kinetics.

Original language	English (US)
Pages (from-to)	2325-2329
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	84
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.8b02993
State	Published - Feb 15 2019

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.8b02993

Fingerprint Dive into the research topics of 'Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site'. Together they form a unique fingerprint.

Cite this

@article{1d3758e74a694d73bd8c055ae0806074,

title = "Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site",

abstract = "A series of bis(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit[7]uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of complex association/dissociation is strongly affected. The relative position (meta, para) of the carboxylate group in relation to the pyridinium nitrogen also exerts a considerable effect on the binding kinetics.",

author = "Iago Neira and Garc{\'i}a, {Marcos D.} and Carlos Peinador and Kaifer, {Angel E.}",

note = "Funding Information: The authors are grateful to the U.S. National Science Foundation (to A.E.K., CHE-1412455) and Ministerio de Economia{\',} Industria y Competitividad (to C.P., MINECO FEDER CTQ2016-75629-P) for the generous support of this work. I.N. acknowledges the MECD (FPU program) for financial support.",

year = "2019",

month = feb,

day = "15",

doi = "10.1021/acs.joc.8b02993",

language = "English (US)",

volume = "84",

pages = "2325--2329",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site

AU - Neira, Iago

AU - García, Marcos D.

AU - Peinador, Carlos

AU - Kaifer, Angel E.

N1 - Funding Information: The authors are grateful to the U.S. National Science Foundation (to A.E.K., CHE-1412455) and Ministerio de Economia,́ Industria y Competitividad (to C.P., MINECO FEDER CTQ2016-75629-P) for the generous support of this work. I.N. acknowledges the MECD (FPU program) for financial support.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - A series of bis(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit[7]uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of complex association/dissociation is strongly affected. The relative position (meta, para) of the carboxylate group in relation to the pyridinium nitrogen also exerts a considerable effect on the binding kinetics.

AB - A series of bis(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit[7]uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of complex association/dissociation is strongly affected. The relative position (meta, para) of the carboxylate group in relation to the pyridinium nitrogen also exerts a considerable effect on the binding kinetics.

UR - http://www.scopus.com/inward/record.url?scp=85061610515&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85061610515&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02993

DO - 10.1021/acs.joc.8b02993

M3 - Article

C2 - 30652476

AN - SCOPUS:85061610515

VL - 84

SP - 2325

EP - 2329

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -