Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution
Abstract
Nine new molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with substituted benzoic acid co-formers have been engineered with varying component stoichiometries (1:1, 1:2 or 1:3). These complexes are all ionic in nature, following proton transfer between the acid co-former and DMAN; the extracted proton is held by DMAN in all instances in an intramolecular [N-H…N]+ hydrogen bond. A number of structural features are common to all complexes and are found to be tunable in a predictable way using systematic acid co-former substitution. These features include charge-assisted hydrogen bonds formed between acid co-formers in hydrogen bonding motifs consistent with complex stoichiometry, and weak hydrogen bonds which facilitate the crystal packing of DMAN and acid co-former components into a regular motif. Possible crystal structure tuning by co-former substitution can aid the rational design of such materials, offering the potential to target solid-state properties that may be influenced by these interactions.Varying the electronic character of the acid co-former substituent group predictably alters weak and strong intermolecular interactions.
- Authors:
-
[1];
[2];
[3];
[2];
[4];
[5];
- Diamond Light Source, Harwell Science and Innovation Campus, Didcot, UK
- Department of Chemistry, University of Bath, Bath, UK
- Department of Chemistry, University of Bath, Bath, UK, School of Physical Sciences
- Advanced Light Source, Lawrence Berkeley National Lab, Berkeley, USA
- Department of Chemistry, University of Bath, Bath, UK, Research Complex at Harwell
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1437501
- Alternate Identifier(s):
- OSTI ID: 1465424
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Published Article
- Journal Name:
- CrystEngComm
- Additional Journal Information:
- Journal Name: CrystEngComm Journal Volume: 20 Journal Issue: 22; Journal ID: ISSN 1466-8033
- Publisher:
- Royal Society of Chemistry (RSC)
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Saunders, Lucy K., Nowell, Harriott, Spencer, Helen C. E., Hatcher, Lauren E., Shepherd, Helena J., Thomas, Lynne H., Jones, Charlotte L., Teat, Simon J., Raithby, Paul R., and Wilson, Chick C. Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. United Kingdom: N. p., 2018.
Web. doi:10.1039/C8CE00443A.
Saunders, Lucy K., Nowell, Harriott, Spencer, Helen C. E., Hatcher, Lauren E., Shepherd, Helena J., Thomas, Lynne H., Jones, Charlotte L., Teat, Simon J., Raithby, Paul R., & Wilson, Chick C. Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. United Kingdom. https://doi.org/10.1039/C8CE00443A
Saunders, Lucy K., Nowell, Harriott, Spencer, Helen C. E., Hatcher, Lauren E., Shepherd, Helena J., Thomas, Lynne H., Jones, Charlotte L., Teat, Simon J., Raithby, Paul R., and Wilson, Chick C. Mon .
"Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution". United Kingdom. https://doi.org/10.1039/C8CE00443A.
@article{osti_1437501,
title = {Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution},
author = {Saunders, Lucy K. and Nowell, Harriott and Spencer, Helen C. E. and Hatcher, Lauren E. and Shepherd, Helena J. and Thomas, Lynne H. and Jones, Charlotte L. and Teat, Simon J. and Raithby, Paul R. and Wilson, Chick C.},
abstractNote = {Nine new molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with substituted benzoic acid co-formers have been engineered with varying component stoichiometries (1:1, 1:2 or 1:3). These complexes are all ionic in nature, following proton transfer between the acid co-former and DMAN; the extracted proton is held by DMAN in all instances in an intramolecular [N-H…N]+ hydrogen bond. A number of structural features are common to all complexes and are found to be tunable in a predictable way using systematic acid co-former substitution. These features include charge-assisted hydrogen bonds formed between acid co-formers in hydrogen bonding motifs consistent with complex stoichiometry, and weak hydrogen bonds which facilitate the crystal packing of DMAN and acid co-former components into a regular motif. Possible crystal structure tuning by co-former substitution can aid the rational design of such materials, offering the potential to target solid-state properties that may be influenced by these interactions.Varying the electronic character of the acid co-former substituent group predictably alters weak and strong intermolecular interactions.},
doi = {10.1039/C8CE00443A},
journal = {CrystEngComm},
number = 22,
volume = 20,
place = {United Kingdom},
year = {Mon Jan 01 00:00:00 EST 2018},
month = {Mon Jan 01 00:00:00 EST 2018}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C8CE00443A
https://doi.org/10.1039/C8CE00443A
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 4 works
Citation information provided by
Web of Science
Web of Science
Figures / Tables:
Scheme 1: The crystal packing of the DMANH+ cation and ACID- anion via weak hydrogen bonding interactions; the hydrogen bonded acid (ACID-) unit is oriented towards the DMAN cation methyl groups.
All figures and tables
(10 total)
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
X-ray, Fourier-transform infrared, 1 H and 13 C nuclear magnetic resonance, and PM3 studies of (N—H⋯N) + and (O—H⋯O) – intramolecular hydrogen bonds in a complex of 1,8-bis(dimethylamino)naphthalene with maleic acid
journal, January 1993
- Bartoszak, Elżbieta; Dega-Szafran, Zofia; Grundwald-Wyspiańska, Monika
- J. Chem. Soc., Faraday Trans., Vol. 89, Issue 12
Systematic experimental charge density analysis of anion receptor complexes
journal, January 2014
- Kirby, Isabelle L.; Brightwell, Mark; Pitak, Mateusz B.
- Phys. Chem. Chem. Phys., Vol. 16, Issue 22
Proton-Transfer-Dependent Reversible Phase Changes in the 4,4′-Bipyridinium Salt of Squaric Acid
journal, February 1994
- Reetz, Manfred T.; Höger, Sigurd; Harms, Klaus
- Angewandte Chemie International Edition in English, Vol. 33, Issue 2
Neutron diffraction of a complex of 1,8-bis(dimethylamino)naphthalene with 1,2-dichloromaleic acid
journal, August 1996
- Wozniak, K.; Wilson, C. C.; Knight, K. S.
- Acta Crystallographica Section B Structural Science, Vol. 52, Issue 4
Structure and energetics of a ferroelectric organic crystal of phenazine and chloranilic acid
journal, September 2012
- Lee, Kyuho; Kolb, Brian; Thonhauser, T.
- Physical Review B, Vol. 86, Issue 10
Supramolecular hydrogen-bonding patterns of co-crystals containing the active pharmaceutical ingredient (API) phloroglucinol and N -heterocycles
journal, May 2016
- Cvetkovski, Aleksandar; Bertolasi, Valerio; Ferretti, Valeria
- Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 3
Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge
journal, March 2016
- Thomas, Lynne H.; Jones, Andrew O. F.; Kallay, Andras A.
- Crystal Growth & Design, Vol. 16, Issue 4
Role of Crystal Packing and Weak Intermolecular Interactions in the Solid State Fluorescence of N -Methylpyrazoline Derivatives
journal, June 2015
- Kupcewicz, Bogumiła; Małecka, Magdalena
- Crystal Growth & Design, Vol. 15, Issue 8
The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge
journal, March 2016
- Jones, Andrew O. F.; Kallay, Andras A.; Lloyd, Hayleigh
- Crystal Growth & Design, Vol. 16, Issue 4
Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing
journal, June 2014
- Vuk, Dragana; Molčanov, Krešimir; Škorić, Irena
- Journal of Molecular Structure, Vol. 1068
Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN) Part 7. The occurrence of a very short asymmetric intermolecular hydrogen bond in the 100 K structure of [DMANH]+·[d-hydrogentartrate]−·trihydrate
journal, November 1992
- Israël, Olaf R.; Kanters, Jan A.; Grech, Eugenius
- Journal of Molecular Structure, Vol. 274
Investigation of Steric Influences on Hydrogen-Bonding Motifs in Cyclic Ureas by Using X-Ray, Neutron, and Computational Methods
journal, August 2013
- McCormick, Laura J.; McDonnell-Worth, Ciaran; Platts, James A.
- Chemistry - An Asian Journal, Vol. 8, Issue 11
Crystallographic studies on sterically affected chemical species Part II. Molecular and crystal structure of 1,8-bis(dimethylamino)- naphthalene tetrafluoroborate. Analysis of distortion of geometry in the aromatic part due to intramolecular hydrogen bonding
journal, November 1990
- Woźniak, K.; Krygowski, T. M.; Kariuki, B.
- Journal of Molecular Structure, Vol. 240
The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges
journal, May 2010
- Sobczyk, L.
- Journal of Molecular Structure, Vol. 972, Issue 1-3
Temperature effect on the structure of the complex 1,8-bis(dimethylamino)naphthalene–chloranilic acid (2/1) dihydrate
journal, October 1991
- Kanters, J. A.; Schouten, A.; Duisenberg, A. J. M.
- Acta Crystallographica Section C Crystal Structure Communications, Vol. 47, Issue 10
Proton transfer in the intramolecular NHN+ bonds in proton sponges with different hydrogen bridge flexibility
journal, January 2009
- Majerz, Irena; Olovsson, Ivar
- Physical Chemistry Chemical Physics, Vol. 11, Issue 9
Role of C?H���O hydrogen bonds in the ionic complexes of 1,8-bis(dimethylamino)naphthalene
journal, January 2003
- Wozniak, Krzysztof; Mallinson, Paul R.; Smith, Garry T.
- Journal of Physical Organic Chemistry, Vol. 16, Issue 10
Tuning Proton Disorder in 3,5-Dinitrobenzoic Acid Dimers: the Effect of Local Environment
journal, January 2013
- Jones, Andrew O. F.; Blagden, Nicholas; McIntyre, Garry J.
- Crystal Growth & Design, Vol. 13, Issue 2
From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene
journal, April 2003
- Mallinson, Paul R.; Smith, Garry T.; Wilson, Chick C.
- Journal of the American Chemical Society, Vol. 125, Issue 14
Organic ferroelectrics
journal, May 2008
- Horiuchi, Sachio; Tokura, Yoshinori
- Nature Materials, Vol. 7, Issue 5, p. 357-366
Ab Initio Studies of Proton Sponges: 1,8-Bis(dimethylamino)naphthalene
journal, August 1994
- Platts, J. A.; Howard, S. T.; Wozniak, K.
- The Journal of Organic Chemistry, Vol. 59, Issue 16
Proton sponges
journal, December 1994
- Llamas-Saiz, A. L.; Foces-Foces, C.; Elguero, J.
- Journal of Molecular Structure, Vol. 328
Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN)
journal, August 1992
- Raves, Mia L.; Kanters, Jan A.; Grech, Eugenius
- Journal of Molecular Structure, Vol. 271, Issue 1-2
The Importance of Weak C−H···O Bonds and π···π Stacking Interactions in the Formation of Organic 1,8-Bis(dimethylamino)naphthalene Complexes with Z ‘ > 1
journal, February 2006
- Nichol, Gary S.; Clegg, William
- Crystal Growth & Design, Vol. 6, Issue 2
Symmetry of N−H−N Hydrogen Bonds in 1,8-Bis(dimethylamino)naphthalene·H + and 2,7-Dimethoxy-1,8-bis(dimethylamino)naphthalene·H +
journal, July 2001
- Perrin, Charles L.; Ohta, Brian K.
- Journal of the American Chemical Society, Vol. 123, Issue 27
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution
journal, December 2015
- Dou, Jin-Hu; Zheng, Yu-Qing; Yao, Ze-Fan
- Journal of the American Chemical Society, Vol. 137, Issue 50
Temperature dependent solid-state proton migration in dimethylurea–oxalic acid complexes
journal, January 2012
- Jones, Andrew O. F.; Lemée-Cailleau, Marie-Hélène; Martins, David M. S.
- Physical Chemistry Chemical Physics, Vol. 14, Issue 38
The Cambridge Structural Database: a quarter of a million crystal structures and rising
journal, May 2002
- Allen, Frank H.
- Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3
Charge Density Distribution in the “Proton Sponge” Compound 1,8-Bis(dimethylamino)naphthalene
journal, May 1999
- Mallinson, Paul R.; Woźniak, Krzysztof; Wilson, Chick C.
- Journal of the American Chemical Society, Vol. 121, Issue 19
Effects of substitution position on crystal packing, polymorphism and crystallization-induced emission of (9-anthryl)vinylstyrylbenzene isomers
journal, January 2016
- Li, Ye-Xin; Yang, Xiao-Feng; Miao, Jin-Ling
- CrystEngComm, Vol. 18, Issue 12
Turning colour on and off using molecular disorder and proton transfer in multi-component molecular complexes
journal, January 2014
- Jones, Charlotte L.; Wilson, Chick C.; Thomas, Lynne H.
- CrystEngComm, Vol. 16, Issue 26
Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas
journal, November 1990
- Etter, Margaret C.; Urbanczyk-Lipkowska, Zofia; Zia-Ebrahimi, Mohammad
- Journal of the American Chemical Society, Vol. 112, Issue 23
Works referencing / citing this record:
CCDC 1831638: Experimental Crystal Structure Determination: LIGSUS : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 4-hydroxybenzoate 4-hydroxybenzoic acid
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- Cambridge Structural Database (CSD)
CCDC 1831639: Experimental Crystal Structure Determination: LIGTAZ : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-aminobenzoate 3-aminobenzoic acid
Space Group: P 21/c (14), Cell: a 9.8631(4)Å b 21.3774(9)Å c 12.5572(5)Å, α 90° β 110.968(2)° γ 90°
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- The Cambridge Crystallographic Data Centre, vp
CCDC 1831640: Experimental Crystal Structure Determination: LIGTED : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 2-cyanobenzoate bis(2-cyanobenzoic acid)
dataset, March 2018
- Saunders, Lucy; Nowell, Harriott; Spencer, Helen
- Cambridge Structural Database (CSD)
CCDC 1831641: Experimental Crystal Structure Determination: LIGTIH : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 2-nitrobenzoate
Space Group: P 21/n (14), Cell: a 10.3320(4)Å b 18.3951(7)Å c 10.3744(4)Å, α 90° β 103.652(2)° γ 90°
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- The Cambridge Crystallographic Data Centre, vp
CCDC 1831642: Experimental Crystal Structure Determination: LIGTON : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-carboxy-5-nitrobenzoate
dataset, March 2018
- Saunders, Lucy; Nowell, Harriott; Spencer, Helen
- Cambridge Structural Database (CSD)
CCDC 1831643: Experimental Crystal Structure Determination: LIGTUT : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-methoxybenzoate 3-methoxybenzoic acid
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- Cambridge Structural Database (CSD)
CCDC 1831644: Experimental Crystal Structure Determination: LIGVAB : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 4-aminobenzoate 4-aminobenzoic acid hydrate
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- Cambridge Structural Database (CSD)
CCDC 1831645: Experimental Crystal Structure Determination
dataset, April 2018
- , Lucy K. Saunders; , Harriott Nowell; , Helen C. E. Spencer
- Cambridge Crystallogrphic Data Centre, vp
CCDC 1831646: Experimental Crystal Structure Determination: LIGVEF : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 4-nitrobenzoate bis(4-nitrobenzoic acid)
Space Group: P 1 (2), Cell: a 14.6269(4)Å b 18.1672(5)Å c 20.9527(6)Å, α 93.416(2)° β 104.461(3)° γ 107.500(3)°
dataset, March 2018
- Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.
- The Cambridge Crystallographic Data Centre, vp
Proton-Transfer-Dependent Reversible Phase Changes in the 4,4′-Bipyridinium Salt of Squaric Acid
journal, February 1994
- Reetz, Manfred T.; Höger, Sigurd; Harms, Klaus
- Angewandte Chemie International Edition in English, Vol. 33, Issue 2
Investigation of Steric Influences on Hydrogen-Bonding Motifs in Cyclic Ureas by Using X-Ray, Neutron, and Computational Methods
journal, August 2013
- McCormick, Laura J.; McDonnell-Worth, Ciaran; Platts, James A.
- Chemistry - An Asian Journal, Vol. 8, Issue 11
Role of C?H���O hydrogen bonds in the ionic complexes of 1,8-bis(dimethylamino)naphthalene
journal, January 2003
- Wozniak, Krzysztof; Mallinson, Paul R.; Smith, Garry T.
- Journal of Physical Organic Chemistry, Vol. 16, Issue 10
Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN)
journal, August 1992
- Raves, Mia L.; Kanters, Jan A.; Grech, Eugenius
- Journal of Molecular Structure, Vol. 271, Issue 1-2
Proton sponges
journal, December 1994
- Llamas-Saiz, A. L.; Foces-Foces, C.; Elguero, J.
- Journal of Molecular Structure, Vol. 328
The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges
journal, May 2010
- Sobczyk, L.
- Journal of Molecular Structure, Vol. 972, Issue 1-3
Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing
journal, June 2014
- Vuk, Dragana; Molčanov, Krešimir; Škorić, Irena
- Journal of Molecular Structure, Vol. 1068
Role of Crystal Packing and Weak Intermolecular Interactions in the Solid State Fluorescence of N -Methylpyrazoline Derivatives
journal, June 2015
- Kupcewicz, Bogumiła; Małecka, Magdalena
- Crystal Growth & Design, Vol. 15, Issue 8
Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge
journal, March 2016
- Thomas, Lynne H.; Jones, Andrew O. F.; Kallay, Andras A.
- Crystal Growth & Design, Vol. 16, Issue 4
The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge
journal, March 2016
- Jones, Andrew O. F.; Kallay, Andras A.; Lloyd, Hayleigh
- Crystal Growth & Design, Vol. 16, Issue 4
The Importance of Weak C−H···O Bonds and π···π Stacking Interactions in the Formation of Organic 1,8-Bis(dimethylamino)naphthalene Complexes with Z ‘ > 1
journal, February 2006
- Nichol, Gary S.; Clegg, William
- Crystal Growth & Design, Vol. 6, Issue 2
Tuning Proton Disorder in 3,5-Dinitrobenzoic Acid Dimers: the Effect of Local Environment
journal, January 2013
- Jones, Andrew O. F.; Blagden, Nicholas; McIntyre, Garry J.
- Crystal Growth & Design, Vol. 13, Issue 2
Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas
journal, November 1990
- Etter, Margaret C.; Urbanczyk-Lipkowska, Zofia; Zia-Ebrahimi, Mohammad
- Journal of the American Chemical Society, Vol. 112, Issue 23
Symmetry of N−H−N Hydrogen Bonds in 1,8-Bis(dimethylamino)naphthalene·H + and 2,7-Dimethoxy-1,8-bis(dimethylamino)naphthalene·H +
journal, July 2001
- Perrin, Charles L.; Ohta, Brian K.
- Journal of the American Chemical Society, Vol. 123, Issue 27
From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene
journal, April 2003
- Mallinson, Paul R.; Smith, Garry T.; Wilson, Chick C.
- Journal of the American Chemical Society, Vol. 125, Issue 14
Charge Density Distribution in the “Proton Sponge” Compound 1,8-Bis(dimethylamino)naphthalene
journal, May 1999
- Mallinson, Paul R.; Woźniak, Krzysztof; Wilson, Chick C.
- Journal of the American Chemical Society, Vol. 121, Issue 19
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution
journal, December 2015
- Dou, Jin-Hu; Zheng, Yu-Qing; Yao, Ze-Fan
- Journal of the American Chemical Society, Vol. 137, Issue 50
Ab Initio Studies of Proton Sponges: 1,8-Bis(dimethylamino)naphthalene
journal, August 1994
- Platts, J. A.; Howard, S. T.; Wozniak, K.
- The Journal of Organic Chemistry, Vol. 59, Issue 16
Organic ferroelectrics
journal, May 2008
- Horiuchi, Sachio; Tokura, Yoshinori
- Nature Materials, Vol. 7, Issue 5, p. 357-366
Proton transfer in the intramolecular NHN+ bonds in proton sponges with different hydrogen bridge flexibility
journal, January 2009
- Majerz, Irena; Olovsson, Ivar
- Physical Chemistry Chemical Physics, Vol. 11, Issue 9
Temperature dependent solid-state proton migration in dimethylurea–oxalic acid complexes
journal, January 2012
- Jones, Andrew O. F.; Lemée-Cailleau, Marie-Hélène; Martins, David M. S.
- Physical Chemistry Chemical Physics, Vol. 14, Issue 38
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.