A conceptual approach to hydrogen bonding

Document Type : Review article

Author

Department of Chemistry Education, Farhangian University, P.O. Box 14665-889, Tehran, Iran

Abstract

Background and Objective: In spite of the fact that the concept of hydrogen bond has been used not only in chemistry but also in other branches of science for more than a century, there is still some doubt about what this basic term means. Due to the importance of hydrogen bond and lately observed experimental results, an attempt has been made to discuss interesting aspects of the hydrogen bonding concept in this review paper, which are not elaborated upon properly in the textbooks. Hopefully, this study will be beneficial for chemistry teachers and students.
Materials and Methods: This study was carried out based on literature survey using reliable scientific databases, such as Google Scholar. In this study, an effort was undertaken to examine the collected data and present a consistent perspective on the definition of hydrogen bond, its categories, some and related aspects.
Findings: A practical definition of hydrogen bonding was obtained by a careful review of the literature. In addition, the various reports about hydrogen bond indicate that it can form not only with nitrogen, oxygen, and fluorine atoms but also, under specific conditions, with other atoms such as boron, carbon, and even hydrogen itself. Subsequent sections are devoted to the discussion of symmetric hydrogen bonds and the results of quantum chemical calculations related to this topic.
Conclusion: This research, focusing on redefinition of the hydrogen bond, offers a comprehensive review about this subject with a special focus on the symmetric hydrogen bond. Regarding the vast information available on hydrogen bond, this article aims to shed light on certain aspects of this peculiar bond. It is recommended that quantum chemical calculations should be used to further investigate hydrogen bond in order to get a deeper and thorough understanding of this intricate chemical bond.

Keywords


Ahmadabadi, Z. (2019). Investigating misconceptions in chemical bonds based on Johnstone’s multi-level thinking model. Research in Chemistry Education, 2(1), 25-40.
Allen, L. C. (1975). Simple model of hydrogen bonding. Journal of American Chemical Society, 97(24), 6921-6940. https://doi.org/10.1021/ja00857a001.
Arunan, E. (2007). Hydrogen bonding and other molecular interactions. Current Science, 92(1), 17-18.
Arunan, E., Desiraju, G. R., Klein, R. A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D. C., Crabtree, R. H., Dannenberg, J. J., Hobza, P., Kjaergaard, H. G., Legon, A. C., Mennucci, B., Nesbitt, D. J.  (2011). Defining the hydrogen bond: An account (IUPAC Technical Report)*. Pure and Applied Chemistry, 83(8), 1619-1636. https://doi:10.1351/PAC-REP-10-01-01.
Azmat, J., Khodai, A. (2019). A study of common misconceptions among students in concepts related to chemical bonds. Research in Chemistry Education, 1(4), 73-89.
Bernal, J. D. (1959). Hydrogen bonding. Hadzi, D., Ed., Pergamon, Elmsford, N. Y.
Buckingham, A. D., Del Bene, J. E., McDowell, S. A. C. (2008). The hydrogen bond. Chemical Physics Letters, 463, 1–10. https://doi.org/10.1016/j.cplett.2008.06.060.   
Calderone, C. T., Williams, D. H. (2001). An enthalpic component in cooperativity: The relationship between enthalpy, entropy, and noncovalent structure in weak associations. Journal of the American Chemical Society, 123(26), 6262-6267. https://doi.org/10.1021/ja003016y.
Carosati, E., Sciabola, S., Cruciani. G. (2004). Hydrogen bonding interactions of covalently bonded fluorine atoms: from crystallographic data to a new angular function in the GRID force field. Journal of Medicinal Chemistry, 47(21), 5114-5125. https://doi.org/10.1021/jm0498349.
Chidambaram, R., Sikka, S. K. (1968). Bent O−H···O hydrogen bonds in crystals. Chemical Physics Letters, 2(3), 162-165. https://doi.org/10.1016/0009-2614(68)85031-6.
Cook, J. L., Hunter, C. A. Low C. M. R., Perez-Velasco, A., Vinter, J. G. (2007). Solvent effects on hydrogen bonding. Angewandte Chemie International Edition, 46, 3706-3709. https://doi.org/10.1002/anie.200604966.
Coulson, C.A. (1957). The hydrogen bond-a review of the present position. Research, 10, 149-159.
Dannenberg, J. J. (2002). Cooperativity in hydrogen bonded aggregates. Models for crystals and peptides. Journal of Molecular Structure, 615(1-3), 219-226. https://doi.org/10.1016/S0022-2860(02)00220-X.
Evans, W. G., Holloway, C. E., Sukumarabandhu, K. McDaniel, D. H. (1968). Strong hydrogen bonds. IV. The B2H7- species. Inorganic Chemistry, 7(9), 1746-1748. https://doi.org/10.1021/ic50067a011.
Fillaux, F., Leygue, N., Tomkinson, J., Cousson, A., Paulus, W. (1991). Structure and dynamics of the symmetric hydrogen bond in potassium hydrogen maleate: a neutron scattering study. Chemical Physics, 244(2-3), 387-403. https://doi.org/10.1016/S0301-0104(99)00153-6.
Gilli, P., Gilli, G. (2009). The nature of the hydrogen bond. Oxford University Press, Oxford. Pauling, L. (1960). The nature of the chemical Bond. Cornell University Press, Ithaca, NY. The first edition was published in 1939.
Grabowski, S. J. (2001). Ab initio calculations on conventional and unconventional hydrogen bonds study of the hydrogen bond strength. Journal of Physical Chemistry A, 105(47), 10739-10746. https://doi.org/10.1021/jp011819h.  
Grabowski, S. J. (Ed.). (2006). Hydrogen bonding: New insights. Springer, Dordrecht.
Grabowski, S. J. (2024). Hydrogen bond types which do not fit accepted definitions. Chemical Communications, 60, 6239-6255. https://doi.org/10.1039/D4CC01769B.
Green, R. D. (1974). Hydrogen bonding by C−H groups. Wiley, New York.
Guillaumes, L., Simon, S., Fonseca Guerra, C. (2015). The role of aromaticity, hybridization, electrostatics, and covalency in resonance-assisted hydrogen bonds of adenine–thymine (AT) base pairs and their mimics. ChemistryOpen, 4(3), 318-327. https://doi.org/10.1002/open.201402132. 
Hadzi, D. (Ed.). (1959). Hydrogen bonding. Pergamon, London.
Haji Abbasi, M., Moradi, S. (2013). Investigating students' weaknesses in understanding the concept of ions and ionic bond formation and providing educational improvement strategies. Research in Chemistry Education, 5(2), 61-70. https://doi.org/10.48310/chemedu.2023.3277.
Henkel, S., Misuraca, M. C., Troselj, P., Davidson, J., Hunter, C. A. (2018). Polarisation effects on the solvation properties of alcohols. Chemical Science, 9, 88-99. https://doi.org/10.1039/c7sc04890d.  
Huggins, M. L. (1971). 50 years of hydrogen bond theory. Angewandte Chemie International Edition, 10, 147-208. https://doi.org/10.1002/anie.197101471.
Huheey, J. E. (1983). Inorganic chemistry: Principles of structure and reactivity. Third edition, Harper & Row.
Jeffrey, G. A. (1998). An introduction on hedrogen bonding (topics in organic physical chemistry). Oxford University, Press, Oxford.
Joesten, M. D., (1982). Hydrogen bonding and proton transfer. Journal of Chemical Education, 59(5), 362-366. https://doi.org/10.1021/ed059p362.  
Karas, L. J., Wu C.-H., Das, R., Wu, J. I-C. (2020). Hydrogen bond design principles. WIREs Computational Molecular Science, 10(6), e1477. https://doi.org/10.1002/wcms.1477.  
Koh, J. T., Cornish, V. W., Schultz, P. G. (1997). An experimental approach to evaluating the role of backbone interactions in proteins using unnatural amino acid mutagenesis. Biochemistry, 36(38), 11314-11322. https://doi.org/10.1021/bi9707685.
Kondo, J., Nakamura, S. (2023). BasePairPuzzle: Molecular models for manipulating the concept of hydrogen bonds and base pairs in nucleic acids. Journal of Chemical Education, 100(2), 946-954. https://doi.org/10.1021/acs.jchemed.2c00964.
Latimer, W. M., Rodebush, W. H. (1920). Polarity and ionization from the standpoint of the Lewis theory of valence. Journal of the American Chemical Society, 42(7), 1419-1433. https://doi.org/10.1021/ja01452a015.
Lee Jr., J. C., Peris, E., Rheingold, A. L., Crabtree, R. H. (1994). An unusual type of H···H interaction: Ir−H···H−O and Ir−H···H−N hydrogen bonding and its involvement in σ-bond metathesis. Journal of the American Chemical Society, 116(24), 11014-11019. https://doi.org/10.1021/ja00103a017.
Latimer, W. M., Rodebush, W. H. (1920). Polarity and ionization from the standpoint of the Lewis theory of valence. Journal of the American Chemical Society, 42(7) 1419-1433. https://doi.org/10.1021/ja01452a015.  
Mammadova, F., Hamarat, B., Ahmadli, D., Şahin, O., Bozkaya, U., Türkmen, Y. E. (2020). Polarization-enhanced hydrogen bonding in 1,8-Dihydroxynaphthalene: Conformational aAnalysis, binding studies and hydrogen bonding catalysis. ChemistrySelect, 5(42), 13387-13396. https://doi.org/10.1002/slct.202002960.
Martín-Fernández, C., Montero-Campillo, M. M., Alkorta, I. (2024). Hydrogen bonds are never of an “anti-electrostatic” nature: a brief tour of a misleading nomenclature. The Journal of Physical Chemistry Letters, 15(15), 4105-4110. https://doi.org/10.1021/acs.jpclett.4c00779.   
Mizushima, S., Simanouti, T., Nagakura, S., Kuratani, K., Tsuboi, M., Baba, H., Fujioka, O. (1950). The molecular structure of N-methylacetamide. Journal of the American Chemical Society, 72(8), 3490-3494. https://doi.org/10.1021/ja01164a048.
Moore, T. S., Winmill, T. F. (1912). The state of amines in aqueous solution. Journal of the Chemical Society, 101, 1635-1676. https://doi.org/10.1039/CT9120101635.  
Meot-Ner, M., (Mautner). (2005). The ionic hydrogen bond. Chemical Reviews, 105(1), 213-284. https://doi.org/10.1021/cr9411785.
Nikro-Shaldehi, N. (2014). Scientific demonstration: an intelligent method in teaching covalent bonding. Research in Chemistry Education, 6(1), 13-4. https://doi.org/10.48310/chemedu.2024.15639.1150.
Pauling, L. (1960). The nature of the chemical bond. Cornell University Press, Ithaca, NY. The first edition was published in 1939.
Pfeiffer, P. (1913). Zur theorie der farblacke, II. Liebig`s Annalen der Chemie, 398(2), 137-196. https://doi.org/10.1002/jlac.19133980203.
Samuel, H. S., Nweke-Maraizu, U., Etim, E. E. (2023). Understanding intermolecular and intramolecular hydrogen bonds: Spectroscopic and computational approaches. Journal of Chemical Reviews, 5(4), 439-465. https://doi.org/10.48309/JCR.2023.407989.1235.
Siddiqui, K. A. (2013). C−H···Onitrate synthon assisted molecular assembly of hydrogen bonded Ni(II) and Cu(II) complexes. Journal of Coordination Chemistry, 66(12), 2039-2050. http://dx.doi.org/10.1080/00958972.2013.797967.  
Stene, R. E., Graubner, T., Ivlev, S. I., Karttunen, A. J., Kraus, F. (2022). A Symmetric F−H−F hydrogen bond in strontium bifluoride, Sr[HF2]2. Zeitschrift fur Anorganische und Allgemeine Chemie, 648(10), Article e202100374. https://doi.org/10.1002/zaac.202100374.
Taylor, R., Kennard, O., Versichel, W. (1983). Geometry of the N−H···O=C hydrogen bond. 1. Lone-pair directionality. Journal of the American Chemical Society, 105(18), 5761-5766. https://doi.org/10.1021/ja00356a010.  
Taylor, R., Kennard, O. (1982). Crystallographic evidence for the existence of C−H−O, C−H−N, and C−H···Cl hydrogen bonds. Journal of the American Chemical Society, 104(19), 5063-5070. https://doi.org/10.1021/ja00383a012.  
Wang, Y., Yu, Z.-X. (2020). Symmetric C···H···C hydrogen bonds predicted by quantum chemical calculations. Journal of Organic Chemistry, 85, 397-402. https://doi.org/10.1021/acs.joc.9b02407.  
Westrum, E. F., Pitzer, K. S. (1949). Thermodynamics of the system KHF2-KF-HF, including heat capacities and entropies of KHF2 and KF. The nature of the hydrogen bond in KHF2. Journal of the American Chemical Society 71(6), 1940-1949. https://doi.org/10.1021/ja01174a012.
Weinhold, F.; Klein, R. A. (2014). "What is a hydrogen bond? Resonance covalency in the supramolecular domain. Chemistry Education Research and Practice. 15(3): 276-285. https://doi.org/10.1039/C4RP00030G. ISSN 1756-1108.
Werner, A. (1902). Ueber Haupt- und nebenvalenzen und die constitution der ammoniumverbindungen, Justus Liebigs Annalen der Chemie, 322(3), 261-296. https://doi.org/10.1002/jlac.19023220302.
Williams, J. M., Schneemeyer, L. F. (1973). Asymmetric single-minimum hydrogen bond in the bifluoride ion. Neutron diffraction study of p-toluidinium bifluoride. Journal of the American Chemical Society, 95(17), 5780-5781. https://doi.org/10.1021/ja00798a067.
Yang, J., Ding, S. J., Radosz, M., Shen, Y. Q. (2004). Reversible catalyst supporting via hydrogen-bonding-mediated self-assembly for atom transfer radical polymerization of MMA. Macromolecules, 37(5), 1728-1734. https://doi.org/10.1021/ma035322c.
Yang, Y., Yang, Z. Y., Yi, Y. P., Xiang, J. F., Chen, C. F., Wan, L. J., Shuai, Z. G. (2007). Helical molecular duplex strands: multiple hydrogen-bond-mediated assembly of self-complementary oligomeric hydrazide derivatives. Journal of Organic Chemistry, 72(13), 4936-4946. https://doi.org/10.1021/jo070525a.
Zhou, Y., Deng, G., Zheng, Y.-Z., Xu, J., Ashraf, H., Yu, Z.-W. (2016). Evidences for cooperative resonance-assisted hydrogen bonds in protein secondary structure analogs, Scientific Reports, 6:36932. https://doi.org/10.1038/srep36932.