Introducing an additional concept in chemical bonding: How effectively can chemistry students comprehend charge-shift bonding?
DOI:
https://doi.org/10.20450/mjcce.2025.3128Keywords:
physical chemistry, chemical bonding, charge-shift bonding, upper-division undergraduate students, graduate education/research studentsAbstract
The development of more modern and effective strategies for teaching chemical bonding theory is a key objective within the chemistry education community. A solid understanding of this concept is essential for comprehending a range of chemistry topics, including the physical and chemical properties of substances, chemical thermodynamics, and polymers – all of which play a vital role in real-world applications. Integrating valence bond (VB) theory, with its strong interpretative capabilities, into the teaching of chemical bonding through information and communication technologies (ICT) can help simplify complex ideas and enhance students' comprehension. This paper presents a structured approach to explaining charge-shift bonding (CSB) within the VB theory framework by calculating the contributions of covalent and ionic VB structures, bond dissociation energy, and resonance energy. Additionally, it introduces unique teaching materials for university teachers and students, combining contemporary teaching tools with classical VB theory. The study involved 47 chemistry students, and the effectiveness of the practical training was assessed using three questionnaires, two knowledge tests (pre-test and post-test), and one survey. Results showed that MSc and PhD students were able to successfully grasp the fundamental concepts of CSB using the proposed approach, while undergraduate students encountered more difficulty. The practical class can serve as a valuable supplement to traditional upper-level instruction on chemical bonding, helping educators and students stay informed about more accurate and modern explanations of bonding in certain molecules.
References
REFERENCES
(1) Hurst O. How We Teach Molecular Structure to Freshmen. J. Chem. Educ. 2002, 79 (6), 763–764, DOI: 10.1021/ed079p763
(2) Ozmen H. Some Student Misconceptions in Chemistry: A Literature Review of Chemical Bonding. J. Sci. Educ. Technol. 2004, 13 (2), 147–159, DOI: 10.1023/B:JOST.0000031255.92943.6d
(3) Vladušić R.; Bucat R. B.; Ožić M. Understanding ionic bonding – a scan across the Croatian education system, Chem. Educ. Res. Pract. 2016, 17, 685-699, DOI: 10.1039/C6RP00040A
(4) Zohar A. R.; Levy S. T. Students' reasoning about chemical bonding: The lacuna of repulsion. J. Res. Sci. Teach. 2019, 56 (7), 881–904. DOI: 10.1002/tea.21532
(5) Koenigsberger L. Hermann von Helmholtz, Braunschweig, F. Vieweg und sohn, 1902.
(6) Abegg R. Die Valenz und das periodische System. Versuch einer Theorie der Molekularverbindungen. Z. Anorg. Chemie. 1904, 39 (1), 330-380, DOI: 10.1002/zaac.19040390125
(7) Kossel W. Über Molekülbildung Als Frage des Atombaus. Ann. Phys. 1916, 354, 229-362, DOI: 10.1002/andp.19163540302
(8) Lewis G. N. The atom and the molecule. J. Am. Chem. Soc. 1916, 38 (4), 762-785, DOI: 10.1021/ja02261a002
(9) Heitler W.; London F. Wechselwirkung neutraler Atome und homöopolare Bindung nach der Quantenmechanik. Z. Phys. 1927, 44, 455-472, DOI: 10.1007/BF01397394
(10) Servos J. W. Physical Chemistry from Ostwald to Pauling. Princeton University Press, 1990.
(11) Brock W. H. The Norton History of Chemistry. W. W. Norton & Co Inc, 1993.
(12) Bensaude-Vincent B.; Stengers I. A History of Chemistry. Harvard University Press, 1996.
(13) Shaik S. The Lewis Legacy: The Chemical Bond - A Territory and Heartland of Chemistry. J. Comput. Chem. 2007, 28, 51-61, DOI: 10.1002/jcc.20517
(14) Kronik L.; Nahum T. L.; Mamlok-Naaman R.; Hofstein A. A New “Bottom-Up” Framework for Teaching Chemical Bonding. J. Chem. Educ. 2008, 85 (12), 1680-1685, DOI: 10.1021/ed085p1680
(15) Tsaparlis G.; Pappa E. T. Evaluation of questions in general chemistry textbooks according to the form of the questions and the Question-Answer Relationship (QAR): the case of intra- and intermolecular chemical bonding. Chem. Educ. Res. Pract. 2011, 12, 262-270, DOI: 10.1039/C1RP90031E
(16) Tsaparlis G.; Pappa E. T.; Byers B. Teaching and learning chemical bonding: research-based evidence for misconceptions and conceptual difficulties experienced by students in upper secondary schools and the effect of an enriched text. Chem. Educ. Res. Pract. 2018, 19, 1253-1269, DOI: 10.1039/C8RP00035B
(17) Sini G.; Maitre P.; Hiberty P. C.; Shaik S. S. Covalent, ionic and resonating single bonds. J. Mol. Struct.: Theochem. 1991, 229, 163-188, DOI: 10.1016/0166-1280(91)90144-9
(18) Shaik S.; Chen Z.; Wu W.; Stanger A.; Danovich D.; Hiberty P. C. An Excursion from Normal to Inverted C-C Bonds Shows Clear Demarcation between Covalent and Charge-Shift Bonds Chemphyschem. 2009, 10 (15), 2658-2669, DOI: 10.1002/cphc.200900633
(19) Shaik S.; Danovich D.; Galbraith J. M.; Braïda B.; Wu W.; Hiberty P. C. Charge-Shift Bonding: A New and Unique Form of Bonding. Angew. Chem. 2020, 59 (3), 984–1001, DOI: 10.1002/anie.201910085
(20) Hiberty P. C.; Danovich D.; Shaik S. A Conversation on New Types of Chemical Bonds. Isr. J. Chem. 2021, 62 (1-2), DOI: 10.1002/ijch.202000114
(21) Heinz M. V.; Reuter L.; Lüchow A. Identifying a real space measure of charge-shift bonding with probability density analysis, Chem. Sci. 2024, 15, 8820-8827, DOI: 10.1039/D4SC01674B
(22) Darling-Hammond L.; Flook L.; Cook-Harvey C.; Barron B.; Osher D. Implications for educational practice of the science of learning and development. Appl. Dev. Sci. 2020, 24 (2), 97-140, DOI: 10.1080/10888691.2018.1537791
(23) Dong A.; Jong M.; King R. B. How Does Prior Knowledge Influence Learning Engagement? The Mediating Roles of Cognitive Load and Help-Seeking. Front. Psychol. 2020, 11, 2992-3002. DOI: 10.3389/fpsyg.2020.591203
(24) Boo H. K. Students’ understandings of chemical bonds and the energetics of chemical reactions. J. Res. Sci. Teach. 1998, 35 (5), 569-581, DOI: 10.1002/(SICI)1098-2736(199805)35:5<569::AID-TEA6>3.0.CO;2-N
(25) Galley W. C. Exothermic Bond Breaking: A Persistent Misconception. J. Chem. Educ. 2004, 81 (4), 523-526, DOI: 10.1021/ed081p523
(26) Ünal S.; Çalik M.; Ayas A.; Coll R. K. A review of chemical bonding studies: needs, aims, methods of exploring students’ conceptions, general knowledge claims and students’ alternative conceptions. Res. Sci. Technol. Educ. 2006, 24 (2), 141-172, DOI: 10.1080/02635140600811536
(27) Luxford C. J.; Bretz S. L. Development of the Bonding Representations Inventory To Identify Student Misconceptions about Covalent and Ionic Bonding Representations. J. Chem. Educ. 2014, 91 (3), 312-320, DOI: 10.1021/ed400700q
(28) Pazinato M. S.; Bernardi F. M.; Miranda A. C. G.; Braibante M. E. F. Epistemological Profile of Chemical Bonding: Evaluation of Knowledge Construction in High School. J. Chem. Educ. 2021, 98 (2), 307-318, DOI: 10.1021/acs.jchemed.0c00353
(29) VandenPlas J. R.; Herrington D. G.; Shrode A. D.; Sweeder R. D. Use of Simulations and Screencasts to Increase Student Understanding of Energy Concepts in Bonding. J. Chem. Educ. 2021, 98 (3), 730-744, DOI: 10.1021/acs.jchemed.0c00470
(30) Peterson R. F.; Treagust D. F. Grade-12 students’ misconceptions of covalent bonding and structure. J. Chem. Educ. 1989, 66 (6), 459–460, DOI: 10.1021/ed066p459
(31) Griffiths A.; Preston K. Grade-12 Students’ Misconceptions Relating to Fundamental Characteristics of Atoms and Molecules. J. Res. Sci. Teach. 1992, 29 (6), 611–628, DOI: 10.1002/tea.3660290609
(32) Herron J. D. The chemistry classroom: Formulas for successful teaching. American Chemical Society, 1996.
(33) Taber K. S. The Mismatch between Assumed Prior Knowledge and the Learner’s Conceptions: A typology of learning impediments. Educ. Stud. 2001, 27 (2), 159–171, DOI: 10.1080/03055690120050392
(34) Nahum T. L.; Mamlok-Naaman R.; Hofstein A.; Krajcik J. Developing a New Teaching Approach for the Chemical Bonding Concept Aligned With Current Scientific and Pedagogical Knowledge. Sci. Ed. 2007, 91 (4), 579–603, DOI: 10.1002/sce.20201
(35) Coll R. K.; Treagust D. F. Investigation of secondary school, undergraduate, and graduate learners’ mental models of ionic bonding. J. Res. Sci. Teach. 2003, 40 (5), 464–486, DOI: 10.1002/tea.10085
(36) Bergqvist A.; Drechsler M.; De Jong O.; Chang Rundgren S. N. Representations of chemical bonding models in school textbooks – help or hindrance for understanding?. Chem. Educ. Res. Pract. 2013, 14, 589-606, DOI: 10.1039/C3RP20159G
(37) Britton B. K.; Woodward A.; Binkley M. Learning From Textbooks; Theory and Practice, Routledge, 1993.
(38) Petruševski, V. M.; Kalajdžievski, S. Heptagonal quasicrystals: Construction of 2D lattices and demonstrations using laser pointers – Concluding part. Maced. J. Chem. Chem. Eng., 2023, 42(1), 127–131. https://doi.org/10.20450/mjcce.2023.2675
(39) Gericke N. M.; Hagberg M. Conceptual Incoherence as a Result of the use of Multiple Historical Models in School Textbooks. Res. Sci. Educ. 2010, 40 (4), 605–623, DOI: 10.1007/s11165-009-9136-y
(40) Dabrowiak J. C.; Hatala P. J.; McPike M. A. Molecular Modeling Program for Teaching Structural Biochemistry. J. Chem. Educ. 2000, 77 (3), 397-400, DOI: 10.1021/ed077p397
(41) Montgomery C. D. Integrating Molecular Modeling into the Inorganic Chemistry Laboratory. J. Chem. Educ. 2001, 78 (6), 840-844, DOI: 10.1021/ed078p840
(42) Milner-Bolotin M. Increasing Interactivity and Authenticity of Chemistry Instruction through Data Acquisition Systems and Other Technologies. J. Chem. Educ. 2012, 89, 477−481, DOI: 10.1021/ed1008443
(43) Valentín A.; Mateos P. M.; González-Tablas M. M.; Pérez L.; López E; García I. Motivation and learning strategies in the use of ICTs among university students. Comput. Educ. 2013, 61, 52–58, DOI: 10.1016/j.compedu.2012.09.008
(44) Aksela M.; Lundell J. Computer-based molecular modelling: Finnish school teachers' experiences and views. Chem. Educ. Res. Pract. 2008, 9, 301-308, DOI: 10.1039/B818464J
(45) Best K. T.; Li D.; Helms E. D. Molecular Modeling of an Electrophilic Addition Reaction with “Unexpected” Regiochemistry. J. Chem. Educ. 2017, 94 (7), 936–940, DOI: 10.1021/acs.jchemed.6b00488
(46) Zohar A. R.; Levy S. T. Attraction vs. repulsion – learning about forces and energy in chemical bonding with the ELI-Chem simulation. Chem. Educ. Res. Pract. 2019, 20, 667-684, DOI: 10.1039/C9RP00007K
(47) Stašević F.; Milanović Ž.; Tošović J.; Đurđević Nikolić J.; Marković S. What Happens When Two Radicals Meet? A Practical Approach to Free Radical Reaction Mechanisms. J. Chem. Educ. 2022, 99 (10), 3522–3529, DOI: 10.1021/acs.jchemed.2c00622
(48) Levine D. S.; Horn P. R.; Mao Y.; Head-Gordon M. Variational Energy Decomposition Analysis of Chemical Bonding. 1. Spin-Pure Analysis of Single Bonds. J. Chem. Theory Comput. 2016, 12 (10), 4812–4820, DOI: 10.1021/acs.jctc.6b00571
(49) Shurki A.; Derat E.; Barrozo A.; Lynn Kamerlin S. C. How valence bond theory can help you understand your (bio) chemical reaction. Chem. Soc. Rev. 2015, 44 (5), 1037-1052. DOI: 10.1039/c4cs00241e
(50) Shaik S.; Danovich D.; Wu W.; Hiberty P. C. Charge-shift bonding and its manifestations in chemistry. Nat. Chem. 2009, 1, 443-449, DOI: 10.1038/nchem.327
(51) Patila A. B.; Bhanage B. Brønsted acidity of protic ionic liquids: a modern ab initio valence bond theory perspective. Phys. Chem. Chem. Phys. 2016, 18, 26020-26025, DOI: 10.1039/C6CP04220A
(52) Rahaman M. Z.; Ge S.; Lin C.; Cui Y.; Wu T. One-Dimensional Molecular Metal Halide Materials: Structures, Properties, and Applications. Small Struct. 2021, 2, 2000062, DOI: 10.1002/sstr.202000062
(53) Đorđević S.; Radenković S.; Shaik S.; Braïda B. On the Nature of the Bonding in Coinage Metal Halides. Molecules. 2022, 27 (2), 490-501, DOI: 10.3390/molecules27020490
(54) Hunter K.; Rodrigues, J-M. G.; Becker N. M. A Review of Research on the Teaching and Learning of Chemical Bonding. J. Chem. Educ. 2022, 99 (7), 2451–2464, DOI: 10.1021/acs.jchemed.2c00034
(55) Glendening E. D.; Landis C. R.; Weinhold F. Natural bond orbital methods. WIREs Comput. Mol. Sci. 2012, 2, 1-42, DOI: 10.1002/wcms.51
(56) Shaik S.; Hiberty P. C. A Chemist's Guide to Valence Bond Theory, Wiley, 2007.
(57) Xiamen University. Xiamen Academy of Chemical Sciences. https://xacs.xmu.edu.cn/ (accessed on January 16, 2025).
(58) Radenković S.; Shaik S. S.; Braïda B. Na⋅⋅⋅B Bond in NaBH3−: Solving the Conundrum. Angew. Chem. 2021, 133 (23), 12833-12836, DOI: 10.1002/ange.202100616
(59) Jain S.; Danovich D.; Radenković S.; Shaik S. Unraveling the Bonding and Aromaticity of Pentazole, Pentaphosphole, and Cyclopentadiene Anions: A Comprehensive Study. J. Am. Chem. Soc. 2025, 147 (1), 1092–1100, DOI: 10.1021/jacs.4c14515
(60) Joy J.; Danovich D.; Kaupp M.; Shaik S. Covalent vs Charge-Shift Nature of the Metal–Metal Bond in Transition Metal Complexes: A Unified Understanding. J. Am. Chem. Soc. 2020, 142 (28), 12277–12287, DOI: 10.1021/jacs.0c03957
(61) Shaik S.; Danovich D.; Zare R. N. Valence Bond Theory Allows a Generalized Description of Hydrogen Bonding. J. Am. Chem. Soc. 2023, 145 (36), 20132–20140, DOI: 10.1021/jacs.3c08196
(62) Pal R.; Patra S. G.; Chattaraj P. K. Can a chemical bond be exclusively covalent or ionic?. J. Chem. Sci. 2022, 134, 108-136, DOI: https://doi.org/10.1007/s12039-022-02094-6
(63) Pauling L. The nature of the chemical bond. application of results obtained from the quantum mechanics and from a theory of paramagnetic susceptibility to the structure of molecules. J. Am. Chem. Soc. 1931, 53 (4), 1367–1400, DOI: 10.1021/ja01355a027
(64) Hoffmann R.; Sason S.; Hiberty P. C. A Conversation on VB vs MO Theory: A Never-Ending Rivalty?. Acc. Chem. Res. 2003, 36 (10), 750-756, DOI: 10.1021/ar030162a
(65) Hiberty P. C.; Braïda B. Pleading for a Dual Molecular-Orbital/Valence-Bond Culture. Angew. Chem. 2018, 57 (21), 5994-6002, DOI: 10.1002/anie.201710094
(66) Galbraith J. M.; Shaik S.; Danovich D.; Braïda B.; Wu W.; Hiberty P.; Cooper D. L.; Karadakov P. B.; Dunning Jr T. H. Valence Bond and Molecular Orbital: Two Powerful Theories that Nicely Complement One Another. J. Chem. Educ. 2021, 98 (12), 3617–3620, DOI: 10.1021/acs.jchemed.1c00919
(67) Shaik S.; Maitre P.; Sini G.; Hiberty P. C. The Charge-Shift Bonding Concept. Electron-Pair Bonds with Very Large Ionic-Covalent Resonance Energies. J. Am. Chem. Soc. 1992, 114, 7861-7866, DOI: doi.org/10.1021/ja00046a035
(68) Lauvergnat D.; Hiberty P. C.; Danovich D.; Shaik S. Comparison of the C-Cl and Si-Cl Bonds. A Valence Bond Study. J. Phys. Chem. 1996, 100, 5715-5720, DOI: 10.1021/jp960145l
(69) Shurki A.; Hiberty P. C.; Shaik S. Charge-Shift Bonding in Group IVB Halides: A Valence Bond Study of MH3−Cl (M = C, Si, Ge, Sn, Pb) Molecules. J. Am. Chem. Soc. 1999, 121 (4), 822-834, DOI: 10.1021/ja982218f
(70) Galbraith J. M.; Blank E.; Shaik S.; Hiberty P. C. π Bonding in Second and Third Row Molecules: Testing the Strength of Linus's Blanket. Chem. Eur. J. 2000, 6 (13), 2425-2434, DOI: 10.1002/1521-3765(20000703)6:13<2425::AID-CHEM2425>3.0.CO;2-0
(71) Wu W.; Gu J.; Song J.; Shaik S.; Hiberty P. C. The Inverted Bond in [1.1.1] Propellane is a Charge-Shift Bond. Angew. Chem. 2009, 48 (8), 1407-1410, DOI: 10.1002/anie.200804965
(72) Ploshnik E.; Danovich D.; Hiberty P. C.; Shaik S. The Nature of the Triple Bonds Between Principal Elements, and the Origin of Trans-Bent Geometries; A Valence Bond Study. J. Chem. Theory Comput. 2011, 7 (4), 955-968, DOI: 10.1021/ct100741b
(73) Radenković S.; Danovich D.; Shaik S.; Hiberty P. C.; Braïda B. The Nature of Bonding in Metal-metal Singly Bonded Coinage Metal Dimers: Cu2, Ag2 and Au2. J. Theor. Comput. Chem. 2017, 1116, 195-201, DOI: 10.1016/j.comptc.2017.02.013
(74) Curriculum for undergraduate academic study in chemistry for obtaining the first degree of higher education and the professional title of Bachelor of Chemistry, Faculty of Science, University of Kragujevac (accessed on September 27, 2022) (in Serbian) https://www.pmf.kg.ac.rs/pub/b546d0d947a34f2c6c72925aec24345a_12022016_124459/oassphemija.pdf
(75) Song L.; Mo Y.; Zhang Q.; Wu W. XMVB: A program for ab initio nonorthogonal valence bond computations. J. Comput. Chem. 2005, 26 (5), 514–521, DOI: 10.1002/jcc.20187
(76) Chen Z.; Ying F.; Chen X.; Song J.; Su P.; Song L.; Mo Y.; Zhang Q.; Wu W. XMVB 2.0: A new version of Xiamen valence bond program. Int. J. Quantum Chem. 2014, 115 (11), 731–737, DOI: 10.1002/qua.24855
(77) Ying F.; Zhou C.; Shurki A.; Danovich D.; Stuyer T.; Braïda B.; Wu. W., (2022), A Tutorial on XMVB. In: Reedijk J. and Krebs B. (eds.), Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Amsterdam: Elsevier. 2022, DOI: 10.1016/B978-0-12-821978-2.00016-7
(78) Huber K. P.; Herzberg G. Constants of diatomic molecules. In: Molecular Spectra and Molecular Structure. Springer, Boston, MA, 1979, pp. 8-689, DOI: 10.1007/978-1-4757-0961-2_2
(79) Luo Y.-R. Comprehensive Handbook of Chemical Bond Energies, CRC Press, 2007.
(80) Zhang L.; Ying F.; Wu W.; Hiberty P. C.; Shaik S. Topology of Electron Charge Density for Chemical Bonds from Valence Bond Theory: A Probe of Bonding Types. Chem. Eur. J. 2009, 15 (12), 2979 – 2989, DOI: 10.1002/chem.200802134
(81) Nugraha A. W.; Sinaga M.; Darmana A.; Sutiani A.; Aini N. Q. The need analysis for computational chemistry based learning media atomic structure and chemical bonding basic chemistry courses. J. Pendidik. Kim. 2024, 16 (1), 30-35, DOI: 10.24114/jpkim.v16i1.56258
(82) Lahlali A.; Chafiq N.; Radid M.; Atibi A.; El Kababi K.; Srour C.; Moundy K. Students’ Alternative Conceptions and Teachers’ Views on the Implementation of Pedagogical Strategies to Improve the Teaching of Chemical Bonding Concepts. Int. J. Eng. Pedagogy. 2023, 13 (6), 90–107, DOI: 10.3991/ijep.v13i6.41391
(83) Nicoll G. A report of undergraduates’ bonding misconceptions. Int. J. Sci. Educ. 2001, 23 (7), 707–730, DOI: 10.1080/09500690010025012
(84) Coll R. K.; Taylor N., Mental models in chemistry: senior chemistry student’s mental models of chemical bonding, Chem. Educ. Res. Pract. 2002, 3 (2), 175-184, DOI: 10.1039/B2RP90014A
(85) Ferguson C. L.; Lockman J. A. Increasing PhD student self-awareness and self-confidence through strengths-based professional development. Front. Educ. 2024, 9, 1379859, DOI: 10.3389/feduc.2024.1379859
(86) Benedict L.; Pence H. E. Teaching Chemistry Using Student-Created Videos and Photo Blogs Accessed with Smartphones and Two-Dimensional Barcodes. J. Chem. Educ. 2012, 89, 492−496, DOI: 10.1021/ed2005399
(87) Gonzalez M. L.; Haza U. J.; Pérez Gramagtes A.; Leon G. F.; Le Bolay N. Supporting Students’ Learning To Learn in General Chemistry Using Moodle. J. Chem. Educ. 2014, 91, 1823−1829, DOI: 10.1021/ed3007605
(88) Abduli S.; Aleksovska S.; Durmishi B. The comparison of different teaching approaches related to the achievements of students’ knowledge and skills. Maced. J. Chem. Chem. Eng., 2015, 34(2), 389–398. https://doi.org/10.20450/mjcce.2015.706
(89) Brailsford I. Motives and aspirations for doctoral study: Career, personal, and inter-personal factors in the decision to embark on a history PhD. Int. J. Dr. Stud., 2010, 5, 15-27, https://doi.org/10.28945/710
(90) Mowbray S.; Halse C. The purpose of the PhD: Theorising the skills acquired by students. High Educ Res Dev, 2010, 29 (6), 653–664, https://doi.org/10.1080/07294360.2010.487199
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