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Opposite-charge repulsive cation and anion pair cooperative organocatalysis in ring-opening polymerization

Cations and anions attract each other by electrostatic force to form an ion pair. However, repulsion between cations and anions does exist. There are few examples of repulsive ion pair strain where catalysis by a strained ion pair is absent. Here, we describe substituted cyclopropenium, the minimal... Full description

Journal Title: Polymer Chemistry 2018, Vol.9(16), pp.2183-2192
Main Author: Xu, Jiaxi
Other Authors: Liu, Jingjing , Li, Zhenjiang , Xu, Songquan , Wang, Haixin , Guo, Tianfo , Gao, Yu , Zhang, Lei , Zhang, Chan , Guo, Kai
Format: Electronic Article Electronic Article
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ID: ISSN: 1759-9954 ; E-ISSN: 1759-9962 ; DOI: 10.1039/c8py00338f
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recordid: rscc8py00338f
title: Opposite-charge repulsive cation and anion pair cooperative organocatalysis in ring-opening polymerization
format: Article
creator:
  • Xu, Jiaxi
  • Liu, Jingjing
  • Li, Zhenjiang
  • Xu, Songquan
  • Wang, Haixin
  • Guo, Tianfo
  • Gao, Yu
  • Zhang, Lei
  • Zhang, Chan
  • Guo, Kai
subjects:
  • Catalysis
  • Cationic Polymerization
  • Benzyl Alcohol
  • Catalysis
  • Anions
  • Ions
  • Ring Opening Polymerization
ispartof: Polymer Chemistry, 2018, Vol.9(16), pp.2183-2192
description: Cations and anions attract each other by electrostatic force to form an ion pair. However, repulsion between cations and anions does exist. There are few examples of repulsive ion pair strain where catalysis by a strained ion pair is absent. Here, we describe substituted cyclopropenium, the minimal Hckel aromatic ring, which when mounted with PhNH groups on the positive cyclopropenium core C 3 , behaves as an electron-rich cation to repel its counter negative anion. The formal positive charge on C 3 turns the NH moiety into a strong H-bond donor (HBD) and the weakly coordinating chloride exhibits strong H-bond acceptor (HBA) character. The strained ion pair composed of a HBD and a HBA displays cooperative organocatalysis in ring-opening polymerizations of -valerolactone initiated with benzyl alcohol. A cooperative catalysis mechanism of tris(phenylamino)cyclopropenium as a HBD and chloride as a HBA was elucidated.
language:
source:
identifier: ISSN: 1759-9954 ; E-ISSN: 1759-9962 ; DOI: 10.1039/c8py00338f
fulltext: fulltext
issn:
  • 1759-9954
  • 1759-9962
  • 17599962
  • 17599954
url: Link


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titleOpposite-charge repulsive cation and anion pair cooperative organocatalysis in ring-opening polymerization
creatorXu, Jiaxi ; Liu, Jingjing ; Li, Zhenjiang ; Xu, Songquan ; Wang, Haixin ; Guo, Tianfo ; Gao, Yu ; Zhang, Lei ; Zhang, Chan ; Guo, Kai
ispartofPolymer Chemistry, 2018, Vol.9(16), pp.2183-2192
identifier
descriptionCations and anions attract each other by electrostatic force to form an ion pair. However, repulsion between cations and anions does exist. There are few examples of repulsive ion pair strain where catalysis by a strained ion pair is absent. Here, we describe substituted cyclopropenium, the minimal Hckel aromatic ring, which when mounted with PhNH groups on the positive cyclopropenium core C 3 , behaves as an electron-rich cation to repel its counter negative anion. The formal positive charge on C 3 turns the NH moiety into a strong H-bond donor (HBD) and the weakly coordinating chloride exhibits strong H-bond acceptor (HBA) character. The strained ion pair composed of a HBD and a HBA displays cooperative organocatalysis in ring-opening polymerizations of -valerolactone initiated with benzyl alcohol. A cooperative catalysis mechanism of tris(phenylamino)cyclopropenium as a HBD and chloride as a HBA was elucidated.
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subjectCatalysis ; Cationic Polymerization ; Benzyl Alcohol ; Catalysis ; Anions ; Ions ; Ring Opening Polymerization;
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titleOpposite-charge repulsive cation and anion pair cooperative organocatalysis in ring-opening polymerization
descriptionCations and anions attract each other by electrostatic force to form an ion pair. However, repulsion between cations and anions does exist. There are few examples of repulsive ion pair strain where catalysis by a strained ion pair is absent. Here, we describe substituted cyclopropenium, the minimal Hckel aromatic ring, which when mounted with PhNH groups on the positive cyclopropenium core C 3 , behaves as an electron-rich cation to repel its counter negative anion. The formal positive charge on C 3 turns the NH moiety into a strong H-bond donor (HBD) and the weakly coordinating chloride exhibits strong H-bond acceptor (HBA) character. The strained ion pair composed of a HBD and a HBA displays cooperative organocatalysis in ring-opening polymerizations of -valerolactone initiated with benzyl alcohol. A cooperative catalysis mechanism of tris(phenylamino)cyclopropenium as a HBD and chloride as a HBA was elucidated.
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titleOpposite-charge repulsive cation and anion pair cooperative organocatalysis in ring-opening polymerization
authorXu, Jiaxi ; Liu, Jingjing ; Li, Zhenjiang ; Xu, Songquan ; Wang, Haixin ; Guo, Tianfo ; Gao, Yu ; Zhang, Lei ; Zhang, Chan ; Guo, Kai
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abstractCations and anions attract each other by electrostatic force to form an ion pair. However, repulsion between cations and anions does exist. There are few examples of repulsive ion pair strain where catalysis by a strained ion pair is absent. Here, we describe substituted cyclopropenium, the minimal Hckel aromatic ring, which when mounted with PhNH groups on the positive cyclopropenium core C 3 , behaves as an electron-rich cation to repel its counter negative anion. The formal positive charge on C 3 turns the NH moiety into a strong H-bond donor (HBD) and the weakly coordinating chloride exhibits strong H-bond acceptor (HBA) character. The strained ion pair composed of a HBD and a HBA displays cooperative organocatalysis in ring-opening polymerizations of -valerolactone initiated with benzyl alcohol. A cooperative catalysis mechanism of tris(phenylamino)cyclopropenium as a HBD and chloride as a HBA was elucidated.
doi10.1039/c8py00338f
pages2183-2192
date2018-04-24