1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

作者: Kevin P. McDonald , Yuran Hua , Amar H. Flood

DOI: 10.1007/7081_2010_38

关键词: Click chemistrySupramolecular chemistryNon-covalent interactionsAnion bindingIonChemistryHydrogen bondCycloadditionComputational chemistryHeteroatom

摘要: As the field of anion supramolecular chemistry continues to grow in its sophistication and understanding noncovalent interactions used effectively bind anions, there exists new theoretical experimental evidence for a necessary reexamination way which views hydrogen bond donors. The heteroatom based hydrogen-bond donors (e.g., NH OH) are well-known provide strong stabilization negatively charged species. However, findings point untapped energy that lay dormant extrinsically-activated CH bonds. Computational studies showed an activated aliphatic or aromatic can amount gas phase approaching conventional Discovery Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition 1,2,3-triazoles ability readily “click” this functionality into receptors has allowed extensive investigation ideas posed by these calculations. This chapter will focus on evolution from being viewed as weak, secondary interaction now utilized powerful source macrocyclic oligomeric receptors. In addition, application binding power 1,2,3-triazole towards preparation mechanically interlocked structures also be discussed.

参考文章(86)
Franz P. Schmidtchen, Reflections on the construction of anion receptors: Is there a sign to resign from design? Coordination Chemistry Reviews. ,vol. 250, pp. 2918- 2928 ,(2006) , 10.1016/J.CCR.2006.07.009
Kristin Bowman-James, Enrique García-España, Antonio Bianchi, Supramolecular chemistry of anions Wiley-VCH. ,(1997)
Gautam R. Desiraju, Thomas Steiner, The Weak Hydrogen Bond: In Structural Chemistry and Biology ,(1999)
Franz Hofmeister, Zur Lehre von der Wirkung der Salze Naunyn-schmiedebergs Archives of Pharmacology. ,vol. 24, pp. 247- 260 ,(1888) , 10.1007/BF01918191
U Oesch, D Ammann, W Simon, Ion-selective membrane electrodes for clinical use. Clinical Chemistry. ,vol. 32, pp. 1448- 1459 ,(1986) , 10.1093/CLINCHEM/32.8.1448
Eric F. V. Scriven, Kenneth Turnbull, Azides: their preparation and synthetic uses Chemical Reviews. ,vol. 88, pp. 297- 368 ,(1988) , 10.1021/CR00084A001
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
Frédéric Coutrot, Camille Romuald, Eric Busseron, A new pH-switchable dimannosyl[c2]daisy chain molecular machine. Organic Letters. ,vol. 10, pp. 3741- 3744 ,(2008) , 10.1021/OL801390H
E.T. Urbansky, M.R. Schock, Issues in managing the risks associated with perchlorate in drinking water Journal of Environmental Management. ,vol. 56, pp. 79- 95 ,(1999) , 10.1006/JEMA.1999.0274