Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

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.

doi:10.1039/C8CE00443A

Title: Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

Journal Article · Mon Jan 01 00:00:00 EST 2018 · CrystEngComm

DOI:https://doi.org/10.1039/C8CE00443A· OSTI ID:1437501

^[1]; Nowell, Harriott ^[1]; Spencer, Helen C. E. ^[2];

^[2];

^[3];

^[2]; Jones, Charlotte L. ^[2];

^[4];

^[5]; Wilson, Chick C. ^[2]

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

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.

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Research Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1437501

Alternate ID(s):: OSTI ID: 1465424

Journal Information:: CrystEngComm, Journal Name: CrystEngComm Vol. 20 Journal Issue: 22; ISSN 1466-8033

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 4 works

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Role of Crystal Packing and Weak Intermolecular Interactions in the Solid State Fluorescence of N -Methylpyrazoline Derivatives Kupcewicz, Bogumiła; Małecka, Magdalena Crystal Growth & Design, Vol. 15, Issue 8 https://doi.org/10.1021/acs.cgd.5b00512	journal	June 2015
The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge Jones, Andrew O. F.; Kallay, Andras A.; Lloyd, Hayleigh Crystal Growth & Design, Vol. 16, Issue 4 https://doi.org/10.1021/acs.cgd.5b01788	journal	March 2016
Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing Vuk, Dragana; Molčanov, Krešimir; Škorić, Irena Journal of Molecular Structure, Vol. 1068 https://doi.org/10.1016/j.molstruc.2014.04.028	journal	June 2014
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Investigation of Steric Influences on Hydrogen-Bonding Motifs in Cyclic Ureas by Using X-Ray, Neutron, and Computational Methods McCormick, Laura J.; McDonnell-Worth, Ciaran; Platts, James A. Chemistry - An Asian Journal, Vol. 8, Issue 11 https://doi.org/10.1002/asia.201300530	journal	August 2013
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Proton transfer in the intramolecular NHN+ bonds in proton sponges with different hydrogen bridge flexibility Majerz, Irena; Olovsson, Ivar Physical Chemistry Chemical Physics, Vol. 11, Issue 9 https://doi.org/10.1039/b814798a	journal	January 2009
Role of C?H��O hydrogen bonds in the ionic complexes of 1,8-bis(dimethylamino)naphthalene Wozniak, Krzysztof; Mallinson, Paul R.; Smith, Garry T. Journal of Physical Organic Chemistry, Vol. 16, Issue 10 https://doi.org/10.1002/poc.683	journal	January 2003
Tuning Proton Disorder in 3,5-Dinitrobenzoic Acid Dimers: the Effect of Local Environment Jones, Andrew O. F.; Blagden, Nicholas; McIntyre, Garry J. Crystal Growth & Design, Vol. 13, Issue 2 https://doi.org/10.1021/cg300906j	journal	January 2013
From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene Mallinson, Paul R.; Smith, Garry T.; Wilson, Chick C. Journal of the American Chemical Society, Vol. 125, Issue 14 https://doi.org/10.1021/ja029389b	journal	April 2003
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Ab Initio Studies of Proton Sponges: 1,8-Bis(dimethylamino)naphthalene Platts, J. A.; Howard, S. T.; Wozniak, K. The Journal of Organic Chemistry, Vol. 59, Issue 16 https://doi.org/10.1021/jo00095a046	journal	August 1994
Proton sponges Llamas-Saiz, A. L.; Foces-Foces, C.; Elguero, J. Journal of Molecular Structure, Vol. 328 https://doi.org/10.1016/0022-2860(94)08367-3	journal	December 1994
Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN) Raves, Mia L.; Kanters, Jan A.; Grech, Eugenius Journal of Molecular Structure, Vol. 271, Issue 1-2 https://doi.org/10.1016/0022-2860(92)80214-3	journal	August 1992
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 Nichol, Gary S.; Clegg, William Crystal Growth & Design, Vol. 6, Issue 2 https://doi.org/10.1021/cg0503806	journal	February 2006
Symmetry of N−H−N Hydrogen Bonds in 1,8-Bis(dimethylamino)naphthalene·H ⁺ and 2,7-Dimethoxy-1,8-bis(dimethylamino)naphthalene·H ⁺ Perrin, Charles L.; Ohta, Brian K. Journal of the American Chemical Society, Vol. 123, Issue 27 https://doi.org/10.1021/ja0036965	journal	July 2001
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution Dou, Jin-Hu; Zheng, Yu-Qing; Yao, Ze-Fan Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11114	journal	December 2015
Temperature dependent solid-state proton migration in dimethylurea–oxalic acid complexes Jones, Andrew O. F.; Lemée-Cailleau, Marie-Hélène; Martins, David M. S. Physical Chemistry Chemical Physics, Vol. 14, Issue 38 https://doi.org/10.1039/c2cp41782k	journal	January 2012
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Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas Etter, Margaret C.; Urbanczyk-Lipkowska, Zofia; Zia-Ebrahimi, Mohammad Journal of the American Chemical Society, Vol. 112, Issue 23 https://doi.org/10.1021/ja00179a028	journal	November 1990

Cited By (30)

CCDC 1831638: Experimental Crystal Structure Determination: LIGSUS : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 4-hydroxybenzoate 4-hydroxybenzoic acid Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. Cambridge Structural Database (CSD) https://doi.org/10.5517/ccdc.csd.cc1zgz3j	dataset	March 2018
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° Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. The Cambridge Crystallographic Data Centre, vp https://doi.org/10.5517/ccdc.csd.cc1zgz4k	dataset	March 2018
CCDC 1831640: Experimental Crystal Structure Determination: LIGTED : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 2-cyanobenzoate bis(2-cyanobenzoic acid) Saunders, Lucy; Nowell, Harriott; Spencer, Helen Cambridge Structural Database (CSD) https://doi.org/10.5517/ccdc.csd.cc1zgz5l	dataset	March 2018
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° Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. The Cambridge Crystallographic Data Centre, vp https://doi.org/10.5517/ccdc.csd.cc1zgz6m	dataset	March 2018
CCDC 1831642: Experimental Crystal Structure Determination: LIGTON : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-carboxy-5-nitrobenzoate Saunders, Lucy; Nowell, Harriott; Spencer, Helen Cambridge Structural Database (CSD) https://doi.org/10.5517/ccdc.csd.cc1zgz7n	dataset	March 2018
CCDC 1831643: Experimental Crystal Structure Determination: LIGTUT : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 3-methoxybenzoate 3-methoxybenzoic acid Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. Cambridge Structural Database (CSD) https://doi.org/10.5517/ccdc.csd.cc1zgz8p	dataset	March 2018
CCDC 1831644: Experimental Crystal Structure Determination: LIGVAB : 8-(dimethylamino)-N,N-dimethylnaphthalen-1-aminium 4-aminobenzoate 4-aminobenzoic acid hydrate Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. Cambridge Structural Database (CSD) https://doi.org/10.5517/ccdc.csd.cc1zgz9q	dataset	March 2018
CCDC 1831645: Experimental Crystal Structure Determination Cambridge Crystallogrphic Data Centre, vp https://doi.org/10.5517/ccdc.csd.cc1zgzbr	dataset	April 2018
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)° Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E. The Cambridge Crystallographic Data Centre, vp https://doi.org/10.5517/ccdc.csd.cc1zgzcs	dataset	March 2018
Proton-Transfer-Dependent Reversible Phase Changes in the 4,4′-Bipyridinium Salt of Squaric Acid Reetz, Manfred T.; Höger, Sigurd; Harms, Klaus Angewandte Chemie International Edition in English, Vol. 33, Issue 2 https://doi.org/10.1002/anie.199401811	journal	February 1994
Investigation of Steric Influences on Hydrogen-Bonding Motifs in Cyclic Ureas by Using X-Ray, Neutron, and Computational Methods McCormick, Laura J.; McDonnell-Worth, Ciaran; Platts, James A. Chemistry - An Asian Journal, Vol. 8, Issue 11 https://doi.org/10.1002/asia.201300530	journal	August 2013
Role of C?H��O hydrogen bonds in the ionic complexes of 1,8-bis(dimethylamino)naphthalene Wozniak, Krzysztof; Mallinson, Paul R.; Smith, Garry T. Journal of Physical Organic Chemistry, Vol. 16, Issue 10 https://doi.org/10.1002/poc.683	journal	January 2003
Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN) Raves, Mia L.; Kanters, Jan A.; Grech, Eugenius Journal of Molecular Structure, Vol. 271, Issue 1-2 https://doi.org/10.1016/0022-2860(92)80214-3	journal	August 1992
Proton sponges Llamas-Saiz, A. L.; Foces-Foces, C.; Elguero, J. Journal of Molecular Structure, Vol. 328 https://doi.org/10.1016/0022-2860(94)08367-3	journal	December 1994
The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges Sobczyk, L. Journal of Molecular Structure, Vol. 972, Issue 1-3 https://doi.org/10.1016/j.molstruc.2009.11.057	journal	May 2010
Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing Vuk, Dragana; Molčanov, Krešimir; Škorić, Irena Journal of Molecular Structure, Vol. 1068 https://doi.org/10.1016/j.molstruc.2014.04.028	journal	June 2014
Role of Crystal Packing and Weak Intermolecular Interactions in the Solid State Fluorescence of N -Methylpyrazoline Derivatives Kupcewicz, Bogumiła; Małecka, Magdalena Crystal Growth & Design, Vol. 15, Issue 8 https://doi.org/10.1021/acs.cgd.5b00512	journal	June 2015
Engineering Short, Strong, Charge-Assisted Hydrogen Bonds in Benzoic Acid Dimers through Cocrystallization with Proton Sponge Thomas, Lynne H.; Jones, Andrew O. F.; Kallay, Andras A. Crystal Growth & Design, Vol. 16, Issue 4 https://doi.org/10.1021/acs.cgd.5b01787	journal	March 2016
The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge Jones, Andrew O. F.; Kallay, Andras A.; Lloyd, Hayleigh Crystal Growth & Design, Vol. 16, Issue 4 https://doi.org/10.1021/acs.cgd.5b01788	journal	March 2016
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 Nichol, Gary S.; Clegg, William Crystal Growth & Design, Vol. 6, Issue 2 https://doi.org/10.1021/cg0503806	journal	February 2006
Tuning Proton Disorder in 3,5-Dinitrobenzoic Acid Dimers: the Effect of Local Environment Jones, Andrew O. F.; Blagden, Nicholas; McIntyre, Garry J. Crystal Growth & Design, Vol. 13, Issue 2 https://doi.org/10.1021/cg300906j	journal	January 2013
Hydrogen bond-directed cocrystallization and molecular recognition properties of diarylureas Etter, Margaret C.; Urbanczyk-Lipkowska, Zofia; Zia-Ebrahimi, Mohammad Journal of the American Chemical Society, Vol. 112, Issue 23 https://doi.org/10.1021/ja00179a028	journal	November 1990
Symmetry of N−H−N Hydrogen Bonds in 1,8-Bis(dimethylamino)naphthalene·H ⁺ and 2,7-Dimethoxy-1,8-bis(dimethylamino)naphthalene·H ⁺ Perrin, Charles L.; Ohta, Brian K. Journal of the American Chemical Society, Vol. 123, Issue 27 https://doi.org/10.1021/ja0036965	journal	July 2001
From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene Mallinson, Paul R.; Smith, Garry T.; Wilson, Chick C. Journal of the American Chemical Society, Vol. 125, Issue 14 https://doi.org/10.1021/ja029389b	journal	April 2003
Charge Density Distribution in the “Proton Sponge” Compound 1,8-Bis(dimethylamino)naphthalene Mallinson, Paul R.; Woźniak, Krzysztof; Wilson, Chick C. Journal of the American Chemical Society, Vol. 121, Issue 19 https://doi.org/10.1021/ja983393z	journal	May 1999
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution Dou, Jin-Hu; Zheng, Yu-Qing; Yao, Ze-Fan Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11114	journal	December 2015
Ab Initio Studies of Proton Sponges: 1,8-Bis(dimethylamino)naphthalene Platts, J. A.; Howard, S. T.; Wozniak, K. The Journal of Organic Chemistry, Vol. 59, Issue 16 https://doi.org/10.1021/jo00095a046	journal	August 1994
Organic ferroelectrics Horiuchi, Sachio; Tokura, Yoshinori Nature Materials, Vol. 7, Issue 5, p. 357-366 https://doi.org/10.1038/nmat2137	journal	May 2008
Proton transfer in the intramolecular NHN+ bonds in proton sponges with different hydrogen bridge flexibility Majerz, Irena; Olovsson, Ivar Physical Chemistry Chemical Physics, Vol. 11, Issue 9 https://doi.org/10.1039/b814798a	journal	January 2009
Temperature dependent solid-state proton migration in dimethylurea–oxalic acid complexes Jones, Andrew O. F.; Lemée-Cailleau, Marie-Hélène; Martins, David M. S. Physical Chemistry Chemical Physics, Vol. 14, Issue 38 https://doi.org/10.1039/c2cp41782k	journal	January 2012

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