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Are Bond Critical Points Really Critical for Hydrogen Bonding?

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† Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand
‡ UPMC Univ Paris 06, UMR 7616 CNRS, Laboratoire de Chimie Théorique, Case Courrier 137, 4 Place Jussieu, F-75005, Paris, France
§ Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand
∥ Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark
*E-mail: [email protected]; [email protected]
Cite this: J. Chem. Theory Comput. 2013, 9, 8, 3263–3266
Publication Date (Web):July 15, 2013
https://doi.org/10.1021/ct400420r
Copyright © 2013 American Chemical Society
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Abstract

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Atoms in Molecules (AIM) theory is routinely used to assess hydrogen bond formation; however its stringent criteria controversially exclude some systems that otherwise appear to exhibit weak hydrogen bonds. We show that a regional analysis of the reduced density gradient, as provided by the recently introduced Non-Covalent Interactions (NCI) index, transcends AIM theory to deliver a chemically intuitive description of hydrogen bonding for a series of 1,n-alkanediols. This regional definition of interactions overcomes the known caveat of only analyzing electron density critical points. In other words, the NCI approach is a simple and elegant generalization of the bond critical point approach, which raises the title question. Namely, is it the presence of an electron density bond critical point that defines a hydrogen bond or the general topology in the region surrounding it?

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Additional theoretical details and results, including the software that was used for the AIM and NCI analyses. This material is available free of charge via the Internet at http://pubs.acs.org.

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  68. Mona Rahimi, Alireza Fattahi. Acidity enhancement of α‐carbon of beta diketones via hydroxyl substituents: A density functional theory study. Journal of Physical Organic Chemistry 2021, 34 (3) https://doi.org/10.1002/poc.4157
  69. Rubén Laplaza, Francesca Peccati, Roberto A. Boto, Chaoyu Quan, Alessandra Carbone, Jean‐Philip Piquemal, Yvon Maday, Julia Contreras‐García. NCIPLOT and the analysis of noncovalent interactions using the reduced density gradient. WIREs Computational Molecular Science 2021, 11 (2) https://doi.org/10.1002/wcms.1497
  70. Ruby Srivastava. Theoretical studies on the electronic and optoelectronic properties of DNA/RNA hybrid-metal complexes. Polyhedron 2021, 196 , 115015. https://doi.org/10.1016/j.poly.2020.115015
  71. Luis R. Domingo, Mar Ríos-Gutiérrez, Nivedita Acharjee. Unveiling the Unexpected Reactivity of Electrophilic Diazoalkanes in [3+2] Cycloaddition Reactions within Molecular Electron Density Theory. Chemistry 2021, 3 (1) , 74-93. https://doi.org/10.3390/chemistry3010006
  72. Ramiro F. Quijano-Quiñones, Jareth Guadarrama-Moreno, Mariana Quesadas-Rojas, Gonzalo J. Mena-Rejón, Carolina S. Castro-Segura, David Cáceres-Castillo. The origin of the regiospecificity of acrolein dimerization. RSC Advances 2021, 11 (13) , 7459-7465. https://doi.org/10.1039/D0RA10084F
  73. Aniruddha Ganguly. On the pivotal roles of non-covalent interactions in governing the conformational stability of halo-salicylic acids: an “atoms-in-molecules” perspective. Structural Chemistry 2021, 32 (1) , 431-443. https://doi.org/10.1007/s11224-020-01638-1
  74. Chenpeng Zuo, Xianwei Zhao, Hetong Wang, Xiaohui Ma, Siyuan Zheng, Fei Xu, Qingzhu Zhang. A theoretical study of hydrogen-bonded molecular clusters of sulfuric acid and organic acids with amides. Journal of Environmental Sciences 2021, 100 , 328-339. https://doi.org/10.1016/j.jes.2020.07.022
  75. Tamanna Poonia, Weslley G.D.P. Silva, Jennifer van Wijngaarden. Derivation of an accurate geometry of 2-fluoroaniline from rotational spectroscopy and computational chemistry. Journal of Molecular Structure 2021, 1225 , 129100. https://doi.org/10.1016/j.molstruc.2020.129100
  76. Menna El Gaafary, Tatiana Syrovets, Hany M. Mohamed, Ahmed A. Elhenawy, Ahmed M. El-Agrody, Abd El-Galil E. Amr, Hazem A. Ghabbour, Abdulrahman A. Almehizia. Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile. Crystals 2021, 11 (2) , 184. https://doi.org/10.3390/cryst11020184
  77. P.C. Sumayya, Godsa Merin Babu, K. Muraleedharan. Quantum chemical investigation of the antiradical property of avenanthramides, oat phenolics. Heliyon 2021, 7 (2) , e06125. https://doi.org/10.1016/j.heliyon.2021.e06125
  78. Peter Politzer, Jane S. Murray. Electrostatic potentials at the nuclei of atoms and molecules. Theoretical Chemistry Accounts 2021, 140 (1) https://doi.org/10.1007/s00214-020-02701-0
  79. L. Leherte. Multiresolution non-covalent interaction analysis for ligand–protein promolecular electron density distributions. Theoretical Chemistry Accounts 2021, 140 (1) https://doi.org/10.1007/s00214-020-02705-w
  80. Steve Scheiner. Insights into the nature of non-covalent bonds accessible by quantum calculations. 2021,,, 39-70. https://doi.org/10.1016/B978-0-12-817586-6.00002-5
  81. Weslley G. D. P. Silva, Tamanna Poonia, Jennifer van Wijngaarden. Exploring the non-covalent interactions behind the formation of amine–water complexes: the case of N -allylmethylamine monohydrate. Physical Chemistry Chemical Physics 2021, 45 https://doi.org/10.1039/D1CP00420D
  82. Fu-de Ren, Wen-jing Shi, Duan-lin Cao, Yong-xiang Li, De-hua Zhang, Xian-feng Wang, Zhao-yang Shi. External electric field reduces the explosive sensitivity: a theoretical investigation into the hydrogen transference kinetics of the NH2NO2∙∙∙H2O complex. Journal of Molecular Modeling 2020, 26 (12) https://doi.org/10.1007/s00894-020-04607-x
  83. Christian Tantardini, Adam A. L. Michalchuk, Artem Samtsevich, Carlo Rota, Alexander G. Kvashnin. The Volumetric Source Function: Looking Inside van der Waals Interactions. Scientific Reports 2020, 10 (1) https://doi.org/10.1038/s41598-020-64261-4
  84. Robin Taylor. Identifying intermolecular atom⋯atom interactions that are not just bonding but also competitive. CrystEngComm 2020, 22 (43) , 7145-7151. https://doi.org/10.1039/D0CE00270D
  85. Frederico Teixeira Silva, Acassio Rocha-Santos, Caio L. Firme, Leonardo A. De Souza, Italo C. Anjos, Jadson C. Belchior. Application of a quantum genetic algorithm and QTAIM analysis in the study of structural and electronic properties of neutral bimetallic clusters NaxLiy (4 ≤ x + y ≤ 10). Journal of Molecular Modeling 2020, 26 (11) https://doi.org/10.1007/s00894-020-04576-1
  86. Abdelmalek Khorief Nacereddine. A MEDT computational study of the mechanism, reactivity and selectivity of non-polar [3+2] cycloaddition between quinazoline-3-oxide and methyl 3-methoxyacrylate. Journal of Molecular Modeling 2020, 26 (11) https://doi.org/10.1007/s00894-020-04585-0
  87. Fabio Meyer, Emanuel Hupf, Enno Lork, Simon Grabowsky, Stefan Mebs, Jens Beckmann. Bis(6‐diphenylphosphino‐acenaphth‐5‐yl)sulfoxide: A New Ligand for Late Transition Metal Complexes. European Journal of Inorganic Chemistry 2020, 2020 (40) , 3829-3836. https://doi.org/10.1002/ejic.202000610
  88. Ruby Srivastava. Interactions, electronic and optical properties of nanographene–peptide complexes: a theoretical study. RSC Advances 2020, 10 (63) , 38654-38662. https://doi.org/10.1039/D0RA07961H
  89. Xingyu Wang, Yan Zhang, Yongsheng Yang, Ying Xue. The mechanism and diastereoselectivity in the formation of trifluoromethyl-containing spiro[pyrrolidin-3,2′-oxindole] by a catalyst-free and mutually activated [3+2]-cycloaddition reaction: a theoretical study. New Journal of Chemistry 2020, 44 (40) , 17465-17476. https://doi.org/10.1039/D0NJ04063K
  90. Rubén Laplaza, Roberto A. Boto, Julia Contreras-García, M. Merced Montero-Campillo. Steric clash in real space: biphenyl revisited. Physical Chemistry Chemical Physics 2020, 22 (37) , 21251-21256. https://doi.org/10.1039/D0CP03359F
  91. D.G. Rego, B.G. Oliveira. The interplay and the formation of σ-hole in the π···LiX and pseudo-π···LiX (X = F, Cl and CN) lithium bonds involving unsaturated and homocyclic hydrocarbons. Computational and Theoretical Chemistry 2020, 1186 , 112899. https://doi.org/10.1016/j.comptc.2020.112899
  92. Gregory A. Anderson, Raghu Nath Behera, Ravi Gomatam. Calculation of higher protonation states and of a new resting state for vanadium chloroperoxidase using QM/MM, with an Atom-in-Molecules analysis. Journal of Molecular Graphics and Modelling 2020, 99 , 107624. https://doi.org/10.1016/j.jmgm.2020.107624
  93. Boaz Galdino de Oliveira, Abedien Zabardasti, Danilo Guimarães do Rego, Mohsen Mohammad Pour. The formation of H···X hydrogen bond, C···X carbon-halide or Si···X tetrel bonds on the silylene-halogen dimers (X = F or Cl): intermolecular strength, molecular orbital interactions and prediction of covalency. Theoretical Chemistry Accounts 2020, 139 (8) https://doi.org/10.1007/s00214-020-02644-6
  94. John S. Lomas, Robert E. Rosenberg, Eric Brémond. Cooperativity in a cycloalkane-1,2/1,3-polyol corona: Topological hydrogen bonding in 1,2-diol motifs. Magnetic Resonance in Chemistry 2020, 91 https://doi.org/10.1002/mrc.5065
  95. Ying-hu Zhao, Fu-de Ren, Li Gao, Ying-xin Tan, Ying-yong Wang. Theoretical explanation for the DNA cleavage by GO with cation: anti-cooperativity effect among the π⋯π, cation⋯π/σ and H-bonding interactions in cytosine⋯GO⋯M n+ (M n+  = Na + , Mg 2+ , Al 3+ ). Molecular Physics 2020, 118 (13) , e1692149. https://doi.org/10.1080/00268976.2019.1692149
  96. Mei‐Yu Yeh, Tzu‐Yu Tseng, Hui‐Chun Hsieh, Bao‐Xing Wu, Yi‐Shun Liao, Yao‐Chun Yeh, Jyun‐Cheng Liu. Amino Acid Residues Vary the Self‐Assembly and Photophysical Properties of Diphenylamine‐Cyanostilbene‐Capped Amphiphiles. ChemPhotoChem 2020, 4 (7) , 481-486. https://doi.org/10.1002/cptc.201900279
  97. John S. Lomas. Cooperativity in alkane-1,2- and 1,3-polyols: NMR, QTAIM, and IQA study of O─H … OH and C─H … OH bonding interactions. Magnetic Resonance in Chemistry 2020, 58 (7) , 666-684. https://doi.org/10.1002/mrc.5014
  98. Nikita E. Safronov, Timur O. Fomin, Artem S. Minin, Lozan Todorov, Irena Kostova, Enrico Benassi, Nataliya P. Belskaya. 5-Amino-2-aryl-1,2,3-triazol-4-carboxylic acids: Synthesis, photophysical properties, and application prospects. Dyes and Pigments 2020, 178 , 108343. https://doi.org/10.1016/j.dyepig.2020.108343
  99. Marcos Juanes, Rizalina Tama Saragi, Yan Jin, Oliver Zingsheim, Stephan Schlemmer, Alberto Lesarri. Rotational spectrum and intramolecular hydrogen bonding in 1,2-butanedithiol. Journal of Molecular Structure 2020, 1211 , 128080. https://doi.org/10.1016/j.molstruc.2020.128080
  100. Daniel Duvinage, Enno Lork, Simon Grabowsky, Stefan Mebs, Jens Beckmann. Synthesis, Structure and Bonding Analysis of the Zwitterionic PPP-Pincer Complex (6-Ph2P-Ace-5-)2P(O)AuCl2. Crystals 2020, 10 (7) , 564. https://doi.org/10.3390/cryst10070564
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