Literature DB >> 20853896

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

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

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.

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Year:  2010        PMID： 20853896      PMCID： PMC2962979          DOI： 10.1021/ja107098r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  30 in total

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2.  A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes.

Authors:  Sung Kuk Kim; Jonathan L Sessler; Dustin E Gross; Chang-Hee Lee; Jong Seung Kim; Vincent M Lynch; Laetitia H Delmau; Benjamin P Hay
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

3.  Influence of substituents on the strength of aryl C-H...anion hydrogen bonds.

Authors:  Vyacheslav S Bryantsev; Benjamin P Hay
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

4.  Aliphatic C-H...anion hydrogen bonds: weak contacts or strong interactions?

Authors:  Lee Pedzisa; Benjamin P Hay
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

5.  Benzene-, pyrrole-, and furan-containing diametrically strapped calix[4]pyrroles--an experimental and theoretical study of hydrogen-bonding effects in chloride anion recognition.

Authors:  Dae-Wi Yoon; Dustin E Gross; Vincent M Lynch; Jonathan L Sessler; Benjamin P Hay; Chang-Hee Lee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Real-time DNA sequencing using detection of pyrophosphate release.

Authors:  M Ronaghi; S Karamohamed; B Pettersson; M Uhlén; P Nyrén
Journal:  Anal Biochem       Date:  1996-11-01       Impact factor: 3.365

7.  Are C-H groups significant hydrogen bonding sites in anion receptors? Benzene complexes with Cl-, NO3-, and ClO4-.

Authors:  Vyacheslav S Bryantsev; Benjamin P Hay
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Dipole-promoted and size-dependent cooperativity between pyridyl-containing triazolophanes and halides leads to persistent sandwich complexes with iodide.

Authors:  Yongjun Li; Maren Pink; Jonathan A Karty; Amar H Flood
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

9.  Anion-arene adducts: C-H hydrogen bonding, anion-pi interaction, and carbon bonding motifs.

Authors:  Benjamin P Hay; Vyacheslav S Bryantsev
Journal:  Chem Commun (Camb)       Date:  2008-03-04       Impact factor: 6.222

10.  1,2,3-Triazole CH...Cl(-) contacts guide anion binding and concomitant folding in 1,4-diaryl triazole oligomers.

Authors:  Hemraj Juwarker; Jeremy M Lenhardt; David M Pham; Stephen L Craig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  7 in total

1.  Structurally Characterized Cationic Silver(I) and Ruthenium(II)carbene complexes of 1,2,3-Triazol-5-ylidenes.

Authors:  Jiajia Cai; Xiaoping Yang; Kuppuswamy Arumugam; Christopher W Bielawski; Jonathan L Sessler
Journal:  Organometallics       Date:  2011-09-26       Impact factor: 3.876

2.  The road to aryl CHanion binding was paved with good intentions: fundamental studies, host design, and historical perspectives in CH hydrogen bonding.

Authors:  Lisa M Eytel; Hazel A Fargher; Michael M Haley; Darren W Johnson
Journal:  Chem Commun (Camb)       Date:  2019-04-04       Impact factor: 6.222

3.  Pyrrole N-H Anion Complexes.

Authors:  Gabriela I Vargas-Zúñiga; Jonathan L Sessler
Journal:  Coord Chem Rev       Date:  2017-04-20       Impact factor: 22.315

4.  A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes.

Authors:  Semin Lee; Chun-Hsing Chen; Amar H Flood
Journal:  Nat Chem       Date:  2013-06-16       Impact factor: 24.427

5.  Anion responsive TTF-appended calix[4]arenes. Synthesis and study of two different conformers.

Authors:  Min Hee Lee; Qian-Yong Cao; Sung Kuk Kim; Jonathan L Sessler; Jong Seung Kim
Journal:  J Org Chem       Date:  2010-12-31       Impact factor: 4.354

6.  Tuning Supramolecular Selectivity for Hydrosulfide: Linear Free Energy Relationships Reveal Preferential C-H Hydrogen Bond Interactions.

Authors:  Hazel A Fargher; Nathanael Lau; H Camille Richardson; Paul Ha-Yeon Cheong; Michael M Haley; Michael D Pluth; Darren W Johnson
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

7.  Ion pair-induced conformational motion in calix[4]arene-strapped calix[4]pyrroles.

Authors:  Sung Kuk Kim; Vincent M Lynch; Benjamin P Hay; Jong Seung Kim; Jonathan L Sessler
Journal:  Chem Sci       Date:  2014-12-03       Impact factor: 9.825
  7 in total

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