Fine tuning the anion binding properties of 2,6-diamidopyridine dipyrromethane hybrid macrocycles

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11442-11446

  Sessler, Jonathan L ^a   Katayev, Evgeny ^a,b   Dan Pantos, G ^a   Scherbakov, Pavel ^b   Reshetova, Marina D ^b   Khrustalev, Victor N ^c   Lynch, Vincent M ^a   Ustynyuk, Yuri A ^b  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; MATHEMATICAL MODELS; NEGATIVE IONS; ORGANIC COMPOUNDS; OXIDATION; PROBABILITY DENSITY FUNCTION; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); TITRATION; ULTRAVIOLET SPECTROSCOPY;

ANION BINDING; CAVITY SIZING; MOLECULAR MODELING;

BINDING ENERGY;

2,6 DIAMINOPYRIDINE; 2,6 DIAMINOPYRIDINE DIPYRROMETHANE; ACETONITRILE; ANION; MACROCYCLIC COMPOUND; METHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; DENSITY FUNCTIONAL THEORY; MOLECULAR MODEL; OXIDATION; SPECTROSCOPY; SYNTHESIS; TITRIMETRY;

EID: 23844518046     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0522938     Document Type: Article

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27. Another factor that could affect the anion binding selectivity of macrocycles 1 and 2 are the minor electronic effects resulting from the changes in the β-pyrrolic substitution patterns. However, on the basis of DFT calculations, we conclude that it is changes in the rigidity of the macrocycle that are mainly responsible for the observed differences in anion selectivity.