Extremely strong contiguous hydrogen bonding arrays

Research output: ThesisDoctoral Thesis

Abstract

When multiple hydrogen bonds lie in-plane and parallel to each other in close proximity, they experience additional positive or negative secondary electrostatic interactions. When a pair of molecules are arranged such that every hydrogen bond acceptor is on one molecule and every hydrogen bond donor is on another, the positive secondary electrostatic interactions are maximised, and thus the association constant of the complex is enhanced. This thesis will present the development of a family of quadruple hydrogen bonded complexes containing only positive secondary interactions, which confers unprecedented stability. The complexes are sufficiently stable to maintain strong binding in polar solvents such as acetonitrile and can be switched “on” and “off” with acid and base. They will be developed into synthons for acid-base responsive supramolecular recognition, for use in stimuli-responsive supramolecular polymers and gelators.
LanguageEnglish
QualificationPhD
Awarding Institution
  • University of Edinburgh
Award date29 Jun 2013
Place of PublicationEdinburgh
Publication statusPublished - 29 Jun 2013
Externally publishedYes

Fingerprint

Hydrogen bonds
Coulomb interactions
Molecules
Acids
Hydrogen
Polymers
Association reactions
acetonitrile

Keywords

  • hydrogen bonds
  • electrostatic interactions
  • bonding arrays

Cite this

@phdthesis{02a9c9042b0745b3a1ab94403b277277,
title = "Extremely strong contiguous hydrogen bonding arrays",
abstract = "When multiple hydrogen bonds lie in-plane and parallel to each other in close proximity, they experience additional positive or negative secondary electrostatic interactions. When a pair of molecules are arranged such that every hydrogen bond acceptor is on one molecule and every hydrogen bond donor is on another, the positive secondary electrostatic interactions are maximised, and thus the association constant of the complex is enhanced. This thesis will present the development of a family of quadruple hydrogen bonded complexes containing only positive secondary interactions, which confers unprecedented stability. The complexes are sufficiently stable to maintain strong binding in polar solvents such as acetonitrile and can be switched “on” and “off” with acid and base. They will be developed into synthons for acid-base responsive supramolecular recognition, for use in stimuli-responsive supramolecular polymers and gelators.",
keywords = "hydrogen bonds, electrostatic interactions, bonding arrays",
author = "Patrick Thomson",
year = "2013",
month = "6",
day = "29",
language = "English",
school = "University of Edinburgh",

}

Thomson, P 2013, 'Extremely strong contiguous hydrogen bonding arrays', PhD, University of Edinburgh, Edinburgh.

Extremely strong contiguous hydrogen bonding arrays. / Thomson, Patrick.

Edinburgh, 2013. 173 p.

Research output: ThesisDoctoral Thesis

TY - THES

T1 - Extremely strong contiguous hydrogen bonding arrays

AU - Thomson, Patrick

PY - 2013/6/29

Y1 - 2013/6/29

N2 - When multiple hydrogen bonds lie in-plane and parallel to each other in close proximity, they experience additional positive or negative secondary electrostatic interactions. When a pair of molecules are arranged such that every hydrogen bond acceptor is on one molecule and every hydrogen bond donor is on another, the positive secondary electrostatic interactions are maximised, and thus the association constant of the complex is enhanced. This thesis will present the development of a family of quadruple hydrogen bonded complexes containing only positive secondary interactions, which confers unprecedented stability. The complexes are sufficiently stable to maintain strong binding in polar solvents such as acetonitrile and can be switched “on” and “off” with acid and base. They will be developed into synthons for acid-base responsive supramolecular recognition, for use in stimuli-responsive supramolecular polymers and gelators.

AB - When multiple hydrogen bonds lie in-plane and parallel to each other in close proximity, they experience additional positive or negative secondary electrostatic interactions. When a pair of molecules are arranged such that every hydrogen bond acceptor is on one molecule and every hydrogen bond donor is on another, the positive secondary electrostatic interactions are maximised, and thus the association constant of the complex is enhanced. This thesis will present the development of a family of quadruple hydrogen bonded complexes containing only positive secondary interactions, which confers unprecedented stability. The complexes are sufficiently stable to maintain strong binding in polar solvents such as acetonitrile and can be switched “on” and “off” with acid and base. They will be developed into synthons for acid-base responsive supramolecular recognition, for use in stimuli-responsive supramolecular polymers and gelators.

KW - hydrogen bonds

KW - electrostatic interactions

KW - bonding arrays

M3 - Doctoral Thesis

CY - Edinburgh

ER -