Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge

Lynne H. Thomas, Andrew Owen Fletcher Jones, Andras A. Kallay, Garry J. McIntyre, Chick C. Wilson

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Abstract

A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with monosubstituted halobenzoic acids are reported, illustrating the designed exploitation of the characteristics of the proton sponge to induce short, charge-assisted hydrogen bonds in a predictable and reproducible manner. In every case, a DMAN molecule extracts a proton from the carboxylic acid group of the benzoic acid, as a result of which a recurrent supramolecular unit between a neutral and a deprotonated benzoic acid molecule is formed, featuring an extremely short, strong O–H···O hydrogen bond, within a predominant crystallization ratio of 1:2 (DMAN:benzoic acid).
Originalspracheenglisch
Seiten (von - bis)2112-2122
FachzeitschriftCrystal growth & design
Jahrgang16
Ausgabenummer4
DOIs
PublikationsstatusVeröffentlicht - 2016

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Benzoic Acid
Benzoic acid
benzoic acid
Naphthalene
naphthalene
Dimers
Protons
Hydrogen bonds
dimers
engineering
hydrogen bonds
protons
Molecules
exploitation
Carboxylic Acids
Crystallization
Carboxylic acids
carboxylic acids
molecules
crystallization

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Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge. / Thomas, Lynne H.; Jones, Andrew Owen Fletcher; Kallay, Andras A.; McIntyre, Garry J.; Wilson, Chick C.

in: Crystal growth & design, Jahrgang 16, Nr. 4, 2016, S. 2112-2122.

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Thomas, Lynne H. ; Jones, Andrew Owen Fletcher ; Kallay, Andras A. ; McIntyre, Garry J. ; Wilson, Chick C. / Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge. in: Crystal growth & design. 2016 ; Jahrgang 16, Nr. 4. S. 2112-2122.
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title = "Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge",
abstract = "A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with monosubstituted halobenzoic acids are reported, illustrating the designed exploitation of the characteristics of the proton sponge to induce short, charge-assisted hydrogen bonds in a predictable and reproducible manner. In every case, a DMAN molecule extracts a proton from the carboxylic acid group of the benzoic acid, as a result of which a recurrent supramolecular unit between a neutral and a deprotonated benzoic acid molecule is formed, featuring an extremely short, strong O–H···O hydrogen bond, within a predominant crystallization ratio of 1:2 (DMAN:benzoic acid).",
author = "Thomas, {Lynne H.} and Jones, {Andrew Owen Fletcher} and Kallay, {Andras A.} and McIntyre, {Garry J.} and Wilson, {Chick C.}",
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T1 - Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge

AU - Thomas, Lynne H.

AU - Jones, Andrew Owen Fletcher

AU - Kallay, Andras A.

AU - McIntyre, Garry J.

AU - Wilson, Chick C.

PY - 2016

Y1 - 2016

N2 - A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with monosubstituted halobenzoic acids are reported, illustrating the designed exploitation of the characteristics of the proton sponge to induce short, charge-assisted hydrogen bonds in a predictable and reproducible manner. In every case, a DMAN molecule extracts a proton from the carboxylic acid group of the benzoic acid, as a result of which a recurrent supramolecular unit between a neutral and a deprotonated benzoic acid molecule is formed, featuring an extremely short, strong O–H···O hydrogen bond, within a predominant crystallization ratio of 1:2 (DMAN:benzoic acid).

AB - A series of molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with monosubstituted halobenzoic acids are reported, illustrating the designed exploitation of the characteristics of the proton sponge to induce short, charge-assisted hydrogen bonds in a predictable and reproducible manner. In every case, a DMAN molecule extracts a proton from the carboxylic acid group of the benzoic acid, as a result of which a recurrent supramolecular unit between a neutral and a deprotonated benzoic acid molecule is formed, featuring an extremely short, strong O–H···O hydrogen bond, within a predominant crystallization ratio of 1:2 (DMAN:benzoic acid).

U2 - 10.1021/acs.cgd.5b01787

DO - 10.1021/acs.cgd.5b01787

M3 - Article

VL - 16

SP - 2112

EP - 2122

JO - Crystal growth & design

JF - Crystal growth & design

SN - 1528-7483

IS - 4

ER -