Formation of pseudo[3]rotaxanes containing calix-bis-crowns and secondary ammonium ions and their thermodynamic stabilities in a solution: preorganization by second macrocycle and nonallosteric behavior exhibited by large crown cavities

• Tokunaga Yuji

• Hayakawa Kentaroh

• Miyashita Junichi

• Kawasaki Tsuneomi

• Miyagawa Shinobu

Abstract

This paper describes the formation of pseudo[3]rotaxanes containing calix[4]-bis-crowns, exhibiting a 1,3-alternate conformation and large crown cavities, and secondary ammonium ions. The first and second association constants of pseudo[3]rotaxane formation are moderate (K1 = 175, K2 = 100 M-1) and are higher than that of the corresponding pseudo[2]rotaxane (K = 24 M-1), consisting of a calix[4]-mono-crown and the same secondary ammonium ion.

Journal

• Tetrahedron Letters

  Tetrahedron Letters 54 (60), 6829-6833, 2013-12

  Elsevier

Keywords

• Rotaxane
• calixarene
• crown ether
• thermodynamic stability
• hydrogen bond

Details

• CRID: 1571135652638358528
• NII Article ID: 120005422967
• Web Site: http://hdl.handle.net/10098/8226
• Text Lang: en
• Data Source:
  • CiNii Articles