Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks
Abstract
Two graphitic carbon nitride (g-C3N4) molecular building blocks designed for halogen bond driven assembly are evaluated through computational quantum chemistry. Unlike those typically reported in the literature, these g-C3N4-based acceptors each offer three unique sites for halogen bond formation, which when introduced to their donor counterparts, lead to 1:1, 2:1, and 3:1 donor-acceptor complexes. Although halogen bonding interactions are present in all donor-acceptor complexes considered in the work, intermolecular hydrogen bonding emerges in complexes in which an iodine-based donor is directly involved. The halogen bond complexes identified herein feature linear halogen bonds and supportive intermolecular hydrogen bonds that lead to nearly additive electronic binding energies of up to -9.7 (dimers), -18.6 (trimers), and -26.5 kcal mol-1 (tetramers). Select vibrational stretching frequencies (νC-X and νC≡C), and the perturbative shifts they incur upon halogen bond formation, are interrogated and compared to those observed in pyridine- and pyrimidine-based halogen-bonded complexes reported in the literature.
- Authors:
-
[1]
- Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, Texas 76798-7348, United States
- Publication Date:
- Research Org.:
- Baylor Univ., Waco, TX (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1735660
- Alternate Identifier(s):
- OSTI ID: 1749885; OSTI ID: 1830731
- Grant/Contract Number:
- SC0019327
- Resource Type:
- Published Article
- Journal Name:
- Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory
- Additional Journal Information:
- Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Volume: 124 Journal Issue: 51; Journal ID: ISSN 1089-5639
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Group theory; Melamine; Oligomers; Complexation; Potential energy
Citation Formats
Devore, Daniel P., Ellington, Thomas L., and Shuford, Kevin L. Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks. United States: N. p., 2020.
Web. doi:10.1021/acs.jpca.0c09154.
Devore, Daniel P., Ellington, Thomas L., & Shuford, Kevin L. Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks. United States. https://doi.org/10.1021/acs.jpca.0c09154
Devore, Daniel P., Ellington, Thomas L., and Shuford, Kevin L. Sat .
"Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks". United States. https://doi.org/10.1021/acs.jpca.0c09154.
@article{osti_1735660,
title = {Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks},
author = {Devore, Daniel P. and Ellington, Thomas L. and Shuford, Kevin L.},
abstractNote = {Two graphitic carbon nitride (g-C3N4) molecular building blocks designed for halogen bond driven assembly are evaluated through computational quantum chemistry. Unlike those typically reported in the literature, these g-C3N4-based acceptors each offer three unique sites for halogen bond formation, which when introduced to their donor counterparts, lead to 1:1, 2:1, and 3:1 donor-acceptor complexes. Although halogen bonding interactions are present in all donor-acceptor complexes considered in the work, intermolecular hydrogen bonding emerges in complexes in which an iodine-based donor is directly involved. The halogen bond complexes identified herein feature linear halogen bonds and supportive intermolecular hydrogen bonds that lead to nearly additive electronic binding energies of up to -9.7 (dimers), -18.6 (trimers), and -26.5 kcal mol-1 (tetramers). Select vibrational stretching frequencies (νC-X and νC≡C), and the perturbative shifts they incur upon halogen bond formation, are interrogated and compared to those observed in pyridine- and pyrimidine-based halogen-bonded complexes reported in the literature.},
doi = {10.1021/acs.jpca.0c09154},
journal = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},
number = 51,
volume = 124,
place = {United States},
year = {Sat Dec 12 00:00:00 EST 2020},
month = {Sat Dec 12 00:00:00 EST 2020}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/acs.jpca.0c09154
https://doi.org/10.1021/acs.jpca.0c09154
Other availability
Search WorldCat to find libraries that may hold this journal
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:
Directional Weak Intermolecular Interactions: σ-Hole Bonding
journal, January 2010
- Murray, Jane S.; Riley, Kevin E.; Politzer, Peter
- Australian Journal of Chemistry, Vol. 63, Issue 12
The Halogen Bond
journal, January 2016
- Cavallo, Gabriella; Metrangolo, Pierangelo; Milani, Roberto
- Chemical Reviews, Vol. 116, Issue 4
Halogen Bonding in Supramolecular Chemistry
journal, August 2008
- Metrangolo, Pierangelo; Meyer, Franck; Pilati, Tullio
- Angewandte Chemie International Edition, Vol. 47, Issue 33
Intermolecular perturbation in the self-assembly of melamine
journal, February 2016
- Petelski, A. N.; Duarte, Darío J. R.; Pamies, S. C.
- Theoretical Chemistry Accounts, Vol. 135, Issue 3
Halogen Bonding in Supramolecular Chemistry
journal, July 2015
- Gilday, Lydia C.; Robinson, Sean W.; Barendt, Timothy A.
- Chemical Reviews, Vol. 115, Issue 15
Crystal engineering. From molecules to materials
journal, August 2003
- Desiraju, Gautam R.
- Journal of Molecular Structure, Vol. 656, Issue 1-3
The Halogen Bond in the Design of Functional Supramolecular Materials: Recent Advances
journal, June 2013
- Priimagi, Arri; Cavallo, Gabriella; Metrangolo, Pierangelo
- Accounts of Chemical Research, Vol. 46, Issue 11
Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure
journal, August 1988
- Carpenter, J. E.; Weinhold, F.
- Journal of Molecular Structure: THEOCHEM, Vol. 169
A grid-based Bader analysis algorithm without lattice bias
journal, January 2009
- Tang, W.; Sanville, E.; Henkelman, G.
- Journal of Physics: Condensed Matter, Vol. 21, Issue 8
Chalcogen Bonding: An Overview
journal, December 2018
- Vogel, Lukas; Wonner, Patrick; Huber, Stefan M.
- Angewandte Chemie International Edition, Vol. 58, Issue 7
Halogen bonding in polymer science: from crystal engineering to functional supramolecular polymers and materials
journal, January 2015
- Berger, Gilles; Soubhye, Jalal; Meyer, Franck
- Polymer Chemistry, Vol. 6, Issue 19
Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different
journal, May 2014
- Mukherjee, Arijit; Tothadi, Srinu; Desiraju, Gautam R.
- Accounts of Chemical Research, Vol. 47, Issue 8
Design and Synthesis of New Tectons for Halogen Bonding-driven Crystal Engineering
journal, April 2003
- Guardigli, Claudio; liantonio, Rosalba; lorenza mele, Maria
- Supramolecular Chemistry, Vol. 15, Issue 3
Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen
journal, January 1989
- Dunning, Thom H.
- The Journal of Chemical Physics, Vol. 90, Issue 2
The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen
journal, January 1996
- Lommerse, Jos P. M.; Stone, Anthony J.; Taylor, Robin
- Journal of the American Chemical Society, Vol. 118, Issue 13
Recent advances in crystal engineering
journal, January 2010
- Aakeröy, Christer B.; Champness, Neil R.; Janiak, Christoph
- CrystEngComm, Vol. 12, Issue 1
On the Spectroscopic and Thermochemical Properties of ClO, BrO, IO, and Their Anions
journal, December 2006
- Peterson, Kirk A.; Shepler, Benjamin C.; Figgen, Detlev
- The Journal of Physical Chemistry A, Vol. 110, Issue 51
A Practical Guide to the Design of Molecular Crystals
journal, December 2018
- Corpinot, Mérina K.; Bučar, Dejan-Krešimir
- Crystal Growth & Design, Vol. 19, Issue 2
A fast and robust algorithm for Bader decomposition of charge density
journal, June 2006
- Henkelman, Graeme; Arnaldsson, Andri; Jónsson, Hannes
- Computational Materials Science, Vol. 36, Issue 3
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions
journal, May 1992
- Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J.
- The Journal of Chemical Physics, Vol. 96, Issue 9
A perspective on quantum mechanics and chemical concepts in describing noncovalent interactions
journal, January 2018
- Clark, Timothy; Murray, Jane S.; Politzer, Peter
- Physical Chemistry Chemical Physics, Vol. 20, Issue 48
Close contacts and noncovalent interactions in crystals
journal, January 2017
- Murray, Jane S.; Resnati, Giuseppe; Politzer, Peter
- Faraday Discussions, Vol. 203
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007
- Zhao, Yan; Truhlar, Donald G.
- Theoretical Chemistry Accounts, Vol. 120, Issue 1-3
Halogen bonding and the design of new materials: organic bromides, chlorides and perhaps even fluorides as donors
journal, March 2007
- Politzer, Peter; Murray, Jane S.; Concha, Monica C.
- Journal of Molecular Modeling, Vol. 13, Issue 6-7
Halogen bond tunability I: the effects of aromatic fluorine substitution on the strengths of halogen-bonding interactions involving chlorine, bromine, and iodine
journal, March 2011
- Riley, Kevin E.; Murray, Jane S.; Fanfrlík, Jindřich
- Journal of Molecular Modeling, Vol. 17, Issue 12
Elucidating the Effects of Fluoro and Nitro Substituents on Halogen Bond Driven Assemblies of Pyridyl-Capped π-Conjugated Molecules
journal, October 2016
- Nguyen, Suong T.; Rheingold, Arnold L.; Tschumper, Gregory S.
- Crystal Growth & Design, Vol. 16, Issue 11
Perspectives on halogen bonding and other σ-hole interactions: Lex parsimoniae (Occam’s Razor)
journal, October 2012
- Politzer, Peter; Riley, Kevin E.; Bulat, Felipe A.
- Computational and Theoretical Chemistry, Vol. 998
Self-Complementary Nonlinear Optical-Phores Targeted to Halogen Bond-Driven Self-Assembly of Electro-Optic Materials
journal, December 2011
- Cariati, Elena; Cavallo, Gabriella; Forni, Alessandra
- Crystal Growth & Design, Vol. 11, Issue 12
Halogen bonding: an electrostatically-driven highly directional noncovalent interaction
journal, January 2010
- Politzer, Peter; Murray, Jane S.; Clark, Timothy
- Physical Chemistry Chemical Physics, Vol. 12, Issue 28
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
journal, September 1988
- Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank
- Chemical Reviews, Vol. 88, Issue 6
The σ-hole revisited
journal, January 2017
- Politzer, Peter; Murray, Jane S.; Clark, Timothy
- Physical Chemistry Chemical Physics, Vol. 19, Issue 48
Halogen Bonding beyond Crystals in Materials Science
journal, September 2019
- Saccone, Marco; Catalano, Luca
- The Journal of Physical Chemistry B, Vol. 123, Issue 44
Accurate and efficient algorithm for Bader charge integration
journal, February 2011
- Yu, Min; Trinkle, Dallas R.
- The Journal of Chemical Physics, Vol. 134, Issue 6
Definition of the halogen bond (IUPAC Recommendations 2013)
journal, July 2013
- Desiraju, Gautam R.; Ho, P. Shing; Kloo, Lars
- Pure and Applied Chemistry, Vol. 85, Issue 8
Decoding chemical information from vibrational spectroscopy data: Local vibrational mode theory
journal, May 2020
- Kraka, Elfi; Zou, Wenli; Tao, Yunwen
- WIREs Computational Molecular Science, Vol. 10, Issue 5
Systematically convergent basis sets with relativistic pseudopotentials. II. Small-core pseudopotentials and correlation consistent basis sets for the post- d group 16–18 elements
journal, December 2003
- Peterson, Kirk A.; Figgen, Detlev; Goll, Erich
- The Journal of Chemical Physics, Vol. 119, Issue 21
Natural population analysis
journal, July 1985
- Reed, Alan E.; Weinstock, Robert B.; Weinhold, Frank
- The Journal of Chemical Physics, Vol. 83, Issue 2
Multiwfn: A multifunctional wavefunction analyzer
journal, December 2011
- Lu, Tian; Chen, Feiwu
- Journal of Computational Chemistry, Vol. 33, Issue 5
Mesoporous carbon nitrides: synthesis, functionalization, and applications
journal, January 2017
- Lakhi, Kripal S.; Park, Dae-Hwan; Al-Bahily, Khalid
- Chemical Society Reviews, Vol. 46, Issue 1
Non-covalent interactions in the synthesis of coordination compounds: Recent advances
journal, August 2017
- Mahmudov, Kamran T.; Kopylovich, Maximilian N.; Guedes da Silva, M. Fátima C.
- Coordination Chemistry Reviews, Vol. 345
Natural localized molecular orbitals
journal, August 1985
- Reed, Alan E.; Weinhold, Frank
- The Journal of Chemical Physics, Vol. 83, Issue 4
Crystal Engineering with Iodoethynylnitrobenzenes: A Group of Highly Effective Halogen-Bond Donors
journal, June 2015
- Aakeröy, Christer B.; Wijethunga, Tharanga K.; Desper, John
- Crystal Growth & Design, Vol. 15, Issue 8
Halogen bonding: A powerful, emerging tool for constructing high-dimensional metal-containing supramolecular networks
journal, February 2016
- Li, Bo; Zang, Shuang-Quan; Wang, Li-Ya
- Coordination Chemistry Reviews, Vol. 308
Natural hybrid orbitals
journal, September 1980
- Foster, J. P.; Weinhold, F.
- Journal of the American Chemical Society, Vol. 102, Issue 24
Halogen Bonds: Benchmarks and Theoretical Analysis
journal, March 2013
- Kozuch, Sebastian; Martin, Jan M. L.
- Journal of Chemical Theory and Computation, Vol. 9, Issue 4
Halogen Bonding: A Paradigm in Supramolecular Chemistry
journal, June 2001
- Metrangolo, Pierangelo; Resnati, Giuseppe
- Chemistry - A European Journal, Vol. 7, Issue 12
Catalysis with Pnictogen, Chalcogen, and Halogen Bonds
journal, March 2018
- Benz, Sebastian; Poblador-Bahamonde, Amalia I.; Low-Ders, Nicolas
- Angewandte Chemie International Edition, Vol. 57, Issue 19
Probing non-covalent interactions driving molecular assembly in organo-electronic building blocks
journal, January 2019
- Johnson, Sarah N.; Ellington, Thomas L.; Ngo, Duong T.
- CrystEngComm, Vol. 21, Issue 20
Engineering functional materials by halogen bonding
journal, January 2006
- Metrangolo, Pierangelo; Resnati, Giuseppe; Pilati, Tullio
- Journal of Polymer Science Part A: Polymer Chemistry, Vol. 45, Issue 1
Halogen bonding: the σ-hole: Proceedings of “Modeling interactions in biomolecules II”, Prague, September 5th–9th, 2005
journal, August 2006
- Clark, Timothy; Hennemann, Matthias; Murray, Jane S.
- Journal of Molecular Modeling, Vol. 13, Issue 2
Mathematical modeling and physical reality in noncovalent interactions
journal, February 2015
- Politzer, Peter; Murray, Jane S.; Clark, Timothy
- Journal of Molecular Modeling, Vol. 21, Issue 3
Halogen bonding and other σ-hole interactions: a perspective
journal, January 2013
- Politzer, Peter; Murray, Jane S.; Clark, Timothy
- Physical Chemistry Chemical Physics, Vol. 15, Issue 27
Halogen bond tunability II: the varying roles of electrostatic and dispersion contributions to attraction in halogen bonds
journal, May 2012
- Riley, Kevin E.; Murray, Jane S.; Fanfrlík, Jindřich
- Journal of Molecular Modeling, Vol. 19, Issue 11
Improved grid-based algorithm for Bader charge allocation
journal, January 2007
- Sanville, Edward; Kenny, Steven D.; Smith, Roger
- Journal of Computational Chemistry, Vol. 28, Issue 5
Editorial: Aggregation of Small Molecules: From Dimers to Crystals
journal, December 2012
- Desiraju, Gautam R.; Johnson, Mark A.; Sander, Wolfram
- ChemPhysChem, Vol. 14, Issue 4
Natural bond orbital analysis of near‐Hartree–Fock water dimer
journal, March 1983
- Reed, Alan E.; Weinhold, Frank
- The Journal of Chemical Physics, Vol. 78, Issue 6
Systematic Experimental and Computational Studies of Substitution and Hybridization Effects in Solid-State Halogen Bonded Assemblies
journal, March 2018
- Nguyen, Suong T.; Ellington, Thomas L.; Allen, Katelyn E.
- Crystal Growth & Design, Vol. 18, Issue 5
VMD: Visual molecular dynamics
journal, February 1996
- Humphrey, William; Dalke, Andrew; Schulten, Klaus
- Journal of Molecular Graphics, Vol. 14, Issue 1