A pyrrolyl-based triazolophane: a macrocyclic receptor with CH and NH donor groups that exhibits a preference for pyrophosphate anions

Jonathan L Sessler; Jiajia Cai; Han-Yuan Gong; Xiaoping Yang; Jonathan F Arambula; Benjamin P Hay

doi:10.1021/ja107098r

A pyrrolyl-based triazolophane: a macrocyclic receptor with CH and NH donor groups that exhibits a preference for pyrophosphate anions

J Am Chem Soc. 2010 Oct 13;132(40):14058-60. doi: 10.1021/ja107098r.

Authors

Jonathan L Sessler¹, Jiajia Cai, Han-Yuan Gong, Xiaoping Yang, Jonathan F Arambula, Benjamin P Hay

Affiliation

¹ Department of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas, Austin, Texas 78712-0165, USA.

Abstract

A pyrrolyl-based triazolophane, incorporating CH and NH donor groups, acts as a receptor for the pyrophosphate anion in chloroform solution. It shows selectivity for this trianion, followed by HSO(4)(-) > H(2)PO(4)(-) > Cl(-) > Br(-) (all as the corresponding tetrabutylammonium salts), with NH-anion interactions being more important than CH-anion interactions. In the solid state, the receptor binds the pyrophosphate anion in a clip-like slot via NH and CH hydrogen bonds.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anions
Diphosphates / chemistry*
Hydrogen Bonding
Pyrroles / chemistry*
Triazoles / chemistry*

Substances

Anions
Diphosphates
Pyrroles
Triazoles

Abstract

Publication types

MeSH terms

Substances

Grants and funding