Counterion influence on the N-I-N halogen bond

J 2015

Counterion influence on the N-I-N halogen bond

BEDIN, Michele, Alavi KARIM, Marcus REITTI, Anna-Carin C. CARLSSON, Filip TOPIC et. al.

Základní údaje

Originální název

Counterion influence on the N-I-N halogen bond

Autoři

BEDIN, Michele (752 Švédsko), Alavi KARIM (752 Švédsko), Marcus REITTI (752 Švédsko), Anna-Carin C. CARLSSON (752 Švédsko), Filip TOPIC (246 Finsko), Mario CETINA (191 Chorvatsko), Fangfang PAN (246 Finsko), Václav HAVEL (203 Česká republika, domácí), Fatima AL-AMERI (752 Švédsko), Vladimír ŠINDELÁŘ (203 Česká republika, domácí), Kari RISSANEN (246 Finsko), Jurgen GRAFENSTEIN (752 Švédsko) a Mate ERDELYI (752 Švédsko, garant)

Vydání

CHEMICAL SCIENCE, CAMBRIDGE (ENGLAND), ROYAL SOC CHEMISTRY, 2015, 2041-6520

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 9.144

Kód RIV

RIV/00216224:14310/15:00081646

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1039/c5sc01053e

UT WoS

000356176200011

Klíčová slova anglicky

EFFECTIVE CORE POTENTIALS; MOLECULAR-ORBITAL METHODS; HYDROGEN-BONDS; IODONIUM NITRATE; BASIS-SET; ELECTROPHILIC ADDITIONS; PENTENYL GLYCOSIDES; RESONANCE-SPECTRA; NMR-SPECTROSCOPY;

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 3. 2016 08:25, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

A detailed investigation of the influence of counterions on the [N-I-N](+) halogen bond in solution, in the solid state and in silico is presented. Translational diffusion coefficients indicate close attachment of counterions to the cationic, three-center halogen bond in dichloromethane solution. Isotopic perturbation of equilibrium NMR studies performed on isotopologue mixtures of regioselectively deuterated and nondeuterated analogues of the model system showed that the counterion is incapable of altering the symmetry of the [N-I-N](+) halogen bond. This symmetry remains even in the presence of an unfavorable geometric restraint. A high preference for the symmetric geometry was found also in the solid state by single crystal X-ray crystallography. Molecular systems encompassing weakly coordinating counterions behave similarly to the corresponding silver(I) centered coordination complexes. In contrast, systems possessing moderately or strongly coordinating anions show a distinctly different behavior. Such silver(I) complexes are converted into multi-coordinate geometries with strong Ag-O bonds, whereas the iodine centered systems remain linear and lack direct charge transfer interaction with the counterion, as verified by N-15 NMR and DFT computation. This suggests that the [N-I-N](+) halogen bond may not be satisfactorily described in terms of a pure coordination bond typical of transition metal complexes, but as a secondary bond with a substantial charge-transfer character.

Návaznosti

GA13-15576S, projekt VaV

Název: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Grantová agentura ČR, Syntéza a supramolekulární vlastnosti bambusurilů

Citovat

BEDIN, Michele, Alavi KARIM, Marcus REITTI, Anna-Carin C. CARLSSON, Filip TOPIC, Mario CETINA, Fangfang PAN, Václav HAVEL, Fatima AL-AMERI, Vladimír ŠINDELÁŘ, Kari RISSANEN, Jurgen GRAFENSTEIN a Mate ERDELYI. Counterion influence on the N-I-N halogen bond. CHEMICAL SCIENCE. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2015, roč. 6, č. 7, s. 3746-3756. ISSN 2041-6520. Dostupné z: https://dx.doi.org/10.1039/c5sc01053e.

@article{1339490,
   author = {Bedin, Michele and Karim, Alavi and Reitti, Marcus and Carlsson, AnnaandCarin C. and Topic, Filip and Cetina, Mario and Pan, Fangfang and Havel, Václav and AlandAmeri, Fatima and Šindelář, Vladimír and Rissanen, Kari and Grafenstein, Jurgen and Erdelyi, Mate},
   article_location = {CAMBRIDGE (ENGLAND)},
   article_number = {7},
   doi = {http://dx.doi.org/10.1039/c5sc01053e},
   keywords = {EFFECTIVE CORE POTENTIALS; MOLECULAR-ORBITAL METHODS; HYDROGEN-BONDS; IODONIUM NITRATE; BASIS-SET; ELECTROPHILIC ADDITIONS; PENTENYL GLYCOSIDES; RESONANCE-SPECTRA; NMR-SPECTROSCOPY;},
   language = {eng},
   issn = {2041-6520},
   journal = {CHEMICAL SCIENCE},
   title = {Counterion influence on the N-I-N halogen bond},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01053E#!divAbstract},
   volume = {6},
   year = {2015}
}

TY  - JOUR
ID  - 1339490
AU  - Bedin, Michele - Karim, Alavi - Reitti, Marcus - Carlsson, Anna-Carin C. - Topic, Filip - Cetina, Mario - Pan, Fangfang - Havel, Václav - Al-Ameri, Fatima - Šindelář, Vladimír - Rissanen, Kari - Grafenstein, Jurgen - Erdelyi, Mate
PY  - 2015
TI  - Counterion influence on the N-I-N halogen bond
JF  - CHEMICAL SCIENCE
VL  - 6
IS  - 7
SP  - 3746-3756
EP  - 3746-3756
PB  - ROYAL SOC CHEMISTRY
SN  - 20416520
KW  - EFFECTIVE CORE POTENTIALS
KW  - MOLECULAR-ORBITAL METHODS
KW  - HYDROGEN-BONDS
KW  - IODONIUM NITRATE
KW  - BASIS-SET
KW  - ELECTROPHILIC ADDITIONS
KW  - PENTENYL GLYCOSIDES
KW  - RESONANCE-SPECTRA
KW  - NMR-SPECTROSCOPY;
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01053E#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01053E#!divAbstract
N2  - A detailed investigation of the influence of counterions on the [N-I-N](+) halogen bond in solution, in the solid state and in silico is presented. Translational diffusion coefficients indicate close attachment of counterions to the cationic, three-center halogen bond in dichloromethane solution. Isotopic perturbation of equilibrium NMR studies performed on isotopologue mixtures of regioselectively deuterated and nondeuterated analogues of the model system showed that the counterion is incapable of altering the symmetry of the [N-I-N](+) halogen bond. This symmetry remains even in the presence of an unfavorable geometric restraint. A high preference for the symmetric geometry was found also in the solid state by single crystal X-ray crystallography. Molecular systems encompassing weakly coordinating counterions behave similarly to the corresponding silver(I) centered coordination complexes. In contrast, systems possessing moderately or strongly coordinating anions show a distinctly different behavior. Such silver(I) complexes are converted into multi-coordinate geometries with strong Ag-O bonds, whereas the iodine centered systems remain linear and lack direct charge transfer interaction with the counterion, as verified by N-15 NMR and DFT computation. This suggests that the [N-I-N](+) halogen bond may not be satisfactorily described in terms of a pure coordination bond typical of transition metal complexes, but as a secondary bond with a substantial charge-transfer character.
ER  -

BEDIN, Michele, Alavi KARIM, Marcus REITTI, Anna-Carin C. CARLSSON, Filip TOPIC, Mario CETINA, Fangfang PAN, Václav HAVEL, Fatima AL-AMERI, Vladimír ŠINDELÁŘ, Kari RISSANEN, Jurgen GRAFENSTEIN a Mate ERDELYI. Counterion influence on the N-I-N halogen bond. \textit{CHEMICAL SCIENCE}. CAMBRIDGE (ENGLAND): ROYAL SOC CHEMISTRY, 2015, roč.~6, č.~7, s.~3746-3756. ISSN~2041-6520. Dostupné z: https://dx.doi.org/10.1039/c5sc01053e.

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