Chiral Guest Binding as a Probe of Macrocycle Dynamics and Tautomerism in a Conjugated Tetrapyrrole

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F14%3A10286275" target="_blank" >RIV/00216208:11320/14:10286275 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1021/ja4124175" target="_blank" >http://dx.doi.org/10.1021/ja4124175</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/ja4124175" target="_blank" >10.1021/ja4124175</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral Guest Binding as a Probe of Macrocycle Dynamics and Tautomerism in a Conjugated Tetrapyrrole

Popis výsledku v původním jazyce

We report chiral guest binding as a probe of prototropic tautomerism and macrocyclic inversion in a highly conjugated tetrapyrrole studied using H-1 NMR spectroscopy in conjunction with mandelic acid as the chiral guest. Both tautomerism and macrocycle inversion can be influenced in a non-trivial way depending on temperature and the respective concentrations of tetrapyrrole host, chiral guest or water. Chirality of the interacting guest is the key feature since it permits separation and detailed observation of macrocyclic inversion and tautornerism. Based on this, a methodology was developed to identify and characterize the dynamic processes. Our observations suggest that yields of products (e.g., of asymmetric reactions) can be affected by reactivityof functional groups (in molecules undergoing tautomerism or inversion) by varying solution properties including reagent concentrations and impurities such as water. This work establishes a connection between the important chemical concep

Název v anglickém jazyce

Chiral Guest Binding as a Probe of Macrocycle Dynamics and Tautomerism in a Conjugated Tetrapyrrole

Popis výsledku anglicky

We report chiral guest binding as a probe of prototropic tautomerism and macrocyclic inversion in a highly conjugated tetrapyrrole studied using H-1 NMR spectroscopy in conjunction with mandelic acid as the chiral guest. Both tautomerism and macrocycle inversion can be influenced in a non-trivial way depending on temperature and the respective concentrations of tetrapyrrole host, chiral guest or water. Chirality of the interacting guest is the key feature since it permits separation and detailed observation of macrocyclic inversion and tautornerism. Based on this, a methodology was developed to identify and characterize the dynamic processes. Our observations suggest that yields of products (e.g., of asymmetric reactions) can be affected by reactivityof functional groups (in molecules undergoing tautomerism or inversion) by varying solution properties including reagent concentrations and impurities such as water. This work establishes a connection between the important chemical concep

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

BM - Fyzika pevných látek a magnetismus

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of the American Chemical Society

ISSN

0002-7863

e-ISSN

—

Svazek periodika

136

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

2112-2118

Kód UT WoS článku

000331493700064

EID výsledku v databázi Scopus

—