Extremely strong contiguous hydrogen bonding arrays

Patrick Thomson

Extremely strong contiguous hydrogen bonding arrays

Research output: Thesis › Doctoral 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.

Language	English
Qualification	PhD
Awarding Institution	University of Edinburgh
Award date	29 Jun 2013
Place of Publication	Edinburgh
Publication status	Published - 29 Jun 2013
Externally published	Yes

Fingerprint

Hydrogen bonds

Coulomb interactions

Molecules

Acids

Hydrogen

Polymers

Association reactions

acetonitrile

Keywords

hydrogen bonds
electrostatic interactions
bonding arrays

Cite this

Thomson, P. (2013). Extremely strong contiguous hydrogen bonding arrays. Edinburgh.

Thomson, Patrick. / Extremely strong contiguous hydrogen bonding arrays. Edinburgh, 2013. 173 p.

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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: Thesis › Doctoral 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 -

Thomson P. Extremely strong contiguous hydrogen bonding arrays. Edinburgh, 2013. 173 p.