The DFT study on the reaction between benzaldehyde and 4-amine-4H-1,2,4-triazole and their derivatives as a source of stable hemiaminals and schiff bases. Effect of substitution and solvation on the reaction mechanism

Journal article


Berski, S., Gordon, A. J. and Ciunik, Z.L. 2015. The DFT study on the reaction between benzaldehyde and 4-amine-4H-1,2,4-triazole and their derivatives as a source of stable hemiaminals and schiff bases. Effect of substitution and solvation on the reaction mechanism. Journal of Molecular Modeling. 21, p. 57. https://doi.org/10.1007/s00894-015-2606-4
AuthorsBerski, S., Gordon, A. J. and Ciunik, Z.L.
Abstract

Reaction mechanism for the benzaldehyde (ald) and 4-amine-4H-1,2,4-triazole (4at) has been investigated at the DFT (B3LYP)/6–31+G(d) computational level. Three transition states (TS) have been identified. The TS1 corresponds to hydrogen transfer from the NH2 group to the C = O bond and nucleophillic attack of the carbon atom from the aldehyde group on the nitrogen atom from the NH2 group in 4at. The result of this reaction is the hemiaminal molecule. The TS2 characterises an internal rearrangement of the benzene and triazole rings in the hemiaminal molecule. The TS3 leads to breaking of the O-H bond, the elimination reaction of the H2O molecule, and formation of the C=N bond. The final product of this reaction is a Schiff base. In order to determine the most favorable conditions for hemiaminal formation, the influence of electronic structure modification on the energetic properties during the reaction of benzaldehyde and 4-amine-4H-1,2,4-triazole has been studied. Thirteen substituents: NH2, OH, OCH3, CH3, F, I, Cl, Br, COH, COOH, CF3, CN, NO2, with different Hammett’s constant values (σ = −0.66–+0.78) have been considered. Finally, the reaction mechanism has been investigated in the presence of 1 to 5 water molecules.

KeywordsBonding; DFT; ELF; Hammett constant; Hemiaminal; Mechanism; Schiff; Substituent
Year2015
JournalJournal of Molecular Modeling
Journal citation21, p. 57
PublisherSpringer Link
Digital Object Identifier (DOI)https://doi.org/10.1007/s00894-015-2606-4
Official URLhttps://link.springer.com/article/10.1007/s00894-015-2606-4
Publication dates
Online21 Feb 2015
Publication process dates
Accepted01 Feb 2015
Deposited17 Apr 2024
Output statusPublished
References

Smith JMB, March J (2007) March’s advanced organic chemistry.
Wiley Interscience, Wiley, 6th edn, pp 1281–1282
2. Forlani L, Marianucci E, Todesco PE (1984) J Chem Res 1984:126
3. Chudek J (1985) A. Foster, R. Young, D. 13C nuclear magnetic resonance studies of the products of reaction of acetaldehyde and of
simple ketones in liquid ammonia, in hydrazine hydrate, and in some
substituted hydrazine solutions. J Chem SocPerkin Trans 2:1285–
1289
4. Iwasawa T, Hooley RJ, Rebek J Jr (2007) Stabilization of labile
carbonyl addition intermediates by a synthetic receptor. Science
317:493–496
5. Hooley RJ, Iwasawa T, Rebek J Jr (2007) Detection of reactive tetrahedral intermediates in a deep cavitand with an introverted functionality. J Am Chem Soc 129:15330–15339
6. Kawamichi T, Haneda T, Kawano M, Fujita M (2009) X-ray observation of a transient hemiaminal trapped in a porous network. Nature
461:633–635
7. Forlani L, Marianucci E, Todesco PE (1984) H-1 nuclear magneticresonance evidence for tetrahedral intermediates in the reactions between aromatic carbonyl groups and aliphatic-amines. J Chem Res-S
4:126–127
8. Dolotko O, Wiench JW, Dennis K, Pecharsky W, Balema VK (2010)
Mechanically induced reactions in organic solids: liquid eutectics or
solid-state processes? New J Chem 34:25–28
9. Suni V, Kurup MRP, Nethaji M (2005) Unusual isolation of a
hemiaminal product from 4-cyclohexyl-3-thiosemicarbazide and di2-pyridyl ketone: structural and spectral investigations. J Mol Struct
749:177–182
10. Barys M, Ciunik Z, Drabent K, Kwiecien A (2010) Stable
hemiaminals containing a triazole ring. New J Chem 34:2605–2611
11. Gaussian 09, Revision D.01, Frisch MJ, Trucks GW, Schlegel HB,
Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V,
Mennucci B, Petersson GA et al. (2009) Gaussian Inc, Wallingford,
CT
12. Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100
13. Becke AD (1993) Density‐functional thermochemistry. III The role
of exact exchange. J Chem Phys 98:5648–5652
14. Lee CT, Yang WT, Parr RG (1988) Development of the Colle-Salvetti
correlation-energy formula into a functional of the electron density.
Phys Rev B 37:785–789
15. Frisch MJ, Pople JA, Binkley JS (1984) Self‐consistent molecular
orbital methods 25. Supplementary functions for Gaussian basis sets.
J Chem Phys 80:3265–3269
16. Fukui K (1970) Formulation of the reaction coordinate. J Phys Chem
74:4161–4163
17. Fukui K (1981) The path of chemical reactions - the IRC approach.
Acc Chem Res 14:363–368
18. Boys SF, Bernardi F (1970) The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol Phys 19:553–566
19. Todd A, Keith TK (2013) AIMAll (Version 12.11.09). Gristmill
Software, Overland Park, KS (aim.tkgristmill.com)
57 Page 16 of 17 J Mol Model (2015) 21: 57
20. Krishnan R, Binkley JS, Seeger R, Pople JA (1980) Self‐consistent
molecular orbital methods. XX A basis set for correlated wave functions. J Chem Phys 72:650–654
21. Clark T, Chandrasekhar J (1983) Schleyer, P.v.R. Efficient diffuse
function-augmented basis sets for anion calculations. III. The 3-21+
G basis set for first-row elements, Li–F. J Comp Chem 4:294–301
22. Noury S, Krokidis X, Fuster F, Silvi B (1997) TopMod, Paris
23. Noury S, Krokidis X, Fuster F, Silvi B (1999) Computational tools
for the electron localization function topological analysis. Comput
Chem 23:597–604
24. Humphrey W, Dalke A, Schulten K (1996) VMD: Visual molecular
dynamics. J Mol Graphics 14:33–38
25. Bader R (1994) Atoms in molecules: a quantum theory. Oxford
University Press, USA
26. Bader R (1991) A quantum theory of molecular structure and its
applications. Chem Rev 91:893–928
27. Fradera X, Austen MA, Bader R (1999) The Lewis model and beyond. J Phys Chem A 103:304–314
28. Becke AD, Edgecombe KE (1990) A simple measure of electron
localization in atomic and molecular systems. J Chem Phys 92:
5397–5403
29. Silvi B, Savin A (1994) Classification of chemical bonds based on
topological analysis of electron localization functions. Nature 371:
683–686
30. Savin A, Silvi B, Colonna F (1996) Topological analysis of the electron localization function applied to delocalized bonds. Can J Chem
74:1088–1096
31. Silvi B (2002) The synaptic order: a key concept to understand multicenter bonding. J Mol Struct 614:3–10
32. Savin A (2005) The electron localization function (ELF) and its relatives: interpretations and difficulties. J Mol Struct (THEOCHEM)
727:127–131
33. Savin A (2005) On the significance of ELF basins. J Chem Sci 117:
473–475
34. Chevreau H, Fuster F, Silvi B (2001) La liaison chimique: mythe ou
réalité. Les méthodes topologiques de description de la liaison.
L’Actual Chim 240:15–22
35. Silvi B, Fourre I, Alikhani ME (2005) The topological analysis of the
electron localization function. A Key for a position space representation of chemical bonds. Monatsh Chem 136:855–879
36. Krokidis X, Goncalves V, Savin A, Silvi B (1998) How malonaldehyde bonds change during proton transfer. J Phys Chem A 102:5065–
5073
37. Berski S, Ciunik LZ The mechanism of the formation of the
hemiaminal and Schiff base from the benzaldehyde and triazole studied by means of the topological analysis of electron localization
function and catastrophe theory. Mol. Phys. DOI: 10.1080/
00268976.2014.974702
38. Hansh C, Leo A, Taft RW (1991) A survey of Hammett substituent
constants and resonance and field parameters. Chem Rev 9l:165–195
39. Cioslowski J (1989) A new population analysis based on atomic
polar tensors. J Am Chem Soc 111:8333–8336
40. Fuster F, Sevin A, Silvi B (2000) Topological analysis of the electron
localization function (ELF) applied to the electrophilic aromatic substitution. J Phys Chem A 104:852–858
41. Fuster F, Sevin A, Silvi B (2000) Determination of substitutional sites
in heterocycles from the topological analysis of the electron localization function (ELF). J Comp Chem 21:509–514
42. Silvi B, Kryachko ES, Tishchenko O, Fuster FT, Nguyen M (2002)
Key properties of monohalogen substituted phenols: interpretation in
terms of the electron localization function. Mol Phys 100:1659–1675
43. Williams IH (1987) Theoretical modelling of specific solvation effects upon carbonyl addition. J Am Chem Soc 109:6299–6307
44. Hall NE, Smith BJ (1998) High-level ab initio molecular orbital
calculations of imine formation. J Phys Chem A 102:4930–4938
45. Feldmann MT, Widicus SL, Blake GA, Kent DR IV, Goddard WA III
(2005) Aminomethanol water elimination: theoretical examination. J
Chem Phys 123:034304–1
46. Erdtman E, Bushnell EAC, Gauld JW, Eriksson LA (2011)
Computational studies on Schiff-base formation: implications for
the catalytic mechanism of porphobilinogen synthase. Comput
Theor Chem 963:479–489

Permalink -

https://repository.canterbury.ac.uk/item/97q02/the-dft-study-on-the-reaction-between-benzaldehyde-and-4-amine-4h-1-2-4-triazole-and-their-derivatives-as-a-source-of-stable-hemiaminals-and-schiff-bases-effect-of-substitution-and-solvation-on-the

  • 30
    total views
  • 0
    total downloads
  • 1
    views this month
  • 0
    downloads this month

Export as

Related outputs

How can we educate future generations to effectively respond to global challenges and live sustainably?
Gordon, A.J. and Simpson, S. 2024. How can we educate future generations to effectively respond to global challenges and live sustainably? in: Billingsley, B., Chappell, K. and Simpson, S. (ed.) The Future of Knowledge: The Role of Epistemic Insight in Interdisciplinary Learning London Bloomsbury. pp. 117-136
Importance of entrepreneurship for students and academics.
Gordon, A.J. 2024. Importance of entrepreneurship for students and academics.
The challenges of leading and managing Polish Saturday schools in the United Kingdom.
Gordon, A. J. and Kozinska, M.A. 2024. The challenges of leading and managing Polish Saturday schools in the United Kingdom.
Building collaborations for a better future: Empowering diverse communities in Kent through collaboration, innovation and research
Gordon, A. J. and Stancu, R. F. 2024. Building collaborations for a better future: Empowering diverse communities in Kent through collaboration, innovation and research.
Creative strategies for implementing digital tools
Gordon, A.J. and Keane, K. 2024. Creative strategies for implementing digital tools .
Harnessing the power of AI in business
Gordon, A. J. and Keane, K. 2024. Harnessing the power of AI in business.
A self-study of teaching teachers using Epistemic Insight
Warhurst, A., Gordon, A.J. and Campbell, R. 2024. A self-study of teaching teachers using Epistemic Insight.
Exploring leadership and entrepreneurship in Polish supplementary schools in England: A pilot study
Gordon, A. J. and Kozinska, M.A. 2024. Exploring leadership and entrepreneurship in Polish supplementary schools in England: A pilot study.
Female entrepreneurship: Challenges and opportunities
Gordon, A.J. 2024. Female entrepreneurship: Challenges and opportunities.
EI STFC Power of Light animation - introducing Big Questions and Diamond Light Source
Cullimore, M., Billingsley, B., Heyes, J. and Gordon, A. EI STFC Power of Light animation - introducing Big Questions and Diamond Light Source. https://doi.org/10.5281/zenodo.7439214
Topological analysis of Electron Localization Function (ELF) as a tool for understanding electronic structure
Berski, S. and Gordon, A. J. 2023. Topological analysis of Electron Localization Function (ELF) as a tool for understanding electronic structure. in: Reference Module in Chemistry, Molecular Sciences and Chemical Engineering Elsevier.
Collaborating to improve teaching and learning about sustainability within an international learning community
Gordon, A., Simpson, S., Lawson, F. and Thomas, C. 2023. Collaborating to improve teaching and learning about sustainability within an international learning community.
Embedding epistemic insight (EI) in teacher training programmes in English universities: barriers and how to overcome them
Billingsley, B., Riga, F., Windsor, Mark and Gordon, A. 2023. Embedding epistemic insight (EI) in teacher training programmes in English universities: barriers and how to overcome them. Teacher Development. https://doi.org/10.1080/13664530.2023.2236056
Co-creation of learning resources that cross disciplinary boundaries within an international learning community
Gordon, A., Thomas, C., Simpson, S. and Lawson, F. 2023. Co-creation of learning resources that cross disciplinary boundaries within an international learning community.
Power of Light – collaborative co-creation of innovative resources for primary science education.
Gordon, A. and Cullimore, M. 2023. Power of Light – collaborative co-creation of innovative resources for primary science education.
Teaching sustainability and stewardship workshop 1: Collaborative approach to developing engagement with science and religion: Exploring sustainability in an international learning community
Gordon, A., Lawson, F., Simpson, S. and Thomas, C. 2023. Teaching sustainability and stewardship workshop 1: Collaborative approach to developing engagement with science and religion: Exploring sustainability in an international learning community.
Leading learning and teaching transformation across the ITE EI consortium –impact across the partner institutions
Gordon, A. 2023. Leading learning and teaching transformation across the ITE EI consortium –impact across the partner institutions.
Do multiple bonds to the boron atom exist?
Berski, S., Mierzwa, G. and Gordon, A. 2023. Do multiple bonds to the boron atom exist?
The Power of Light Zine 3 - Why do we explore the world around us? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK
Cullimore, M., Halford, K., Day, S,, Gordon, A., Billingsley, B. and Mosselmans, F. 2022. The Power of Light Zine 3 - Why do we explore the world around us? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK. https://doi.org/10.5281/zenodo.7438811
The Power of Light Zine 2 - Why does life exist? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK
Cullimore, M., Geraki, T., Linton, P., Gordon, A., Billingsley, B. and Halford, K. 2022. The Power of Light Zine 2 - Why does life exist? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK. https://doi.org/10.5281/zenodo.7438698
The Power of Light Zine 1 - Why do things change? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK
Cullimore, M., Halford, K., Mosselmans, F., Reeve, L., Billingsley, B. and Gordon, A. 2022. The Power of Light Zine 1 - Why do things change? - an epistemically insightful way to explore the nature of science and research at Diamond Light Source, UK. https://doi.org/10.5281/zenodo.7401129
CPD 1 - Embedding Epistemic Insight and Big Questions across a whole school curriculum
Simpson, S. and Gordon, A. 2022. CPD 1 - Embedding Epistemic Insight and Big Questions across a whole school curriculum. https://doi.org/10.5281/zenodo.7729394
Creating epistemically insightful learning experiences in primary classrooms: insights into the nature of science
Gordon, A., Simpson, S. and Lawson, F. 2022. Creating epistemically insightful learning experiences in primary classrooms: insights into the nature of science.
Transforming teacher education - introducing ITE students to Epistemic Insight: a workshop
Warhurst, A., Campbell, R. and Gordon, A.J. 2022. Transforming teacher education - introducing ITE students to Epistemic Insight: a workshop.
Bristlebots and other friends. A progression of Epistemic insight workshops using small things to ask big questions
Bentley, K., Gordon, A.J. and Litchfield, A. 2022. Bristlebots and other friends. A progression of Epistemic insight workshops using small things to ask big questions.
Science, religion and sustainability in schools: outlining a teacher learning community approach.
Gordon, A.J., Lawson, F., Simpson, S. and Thomas, C. 2022. Science, religion and sustainability in schools: outlining a teacher learning community approach.
The epistemic insight digest: Issue : Autumn 2022
Gordon, A., Shalet, D., Simpson, S., Hassanin, H., Lawson, F., Lawson, M., Litchfield, A., Thomas, C., Canetta, E., Manley, K. and Choong, C. Shalet, D. (ed.) 2022. The epistemic insight digest: Issue : Autumn 2022. Canterbury Canterbury Christ Church University.
Leading transformation in ITE teaching within the EI consortium
Gordon, A.J. 2022. Leading transformation in ITE teaching within the EI consortium.
The epistemic insight digest: Issue 4: Spring 2022
Gordon, A., Cullimore, M., Hackett, L., Shalet, D., Jennings, B-L, Semaan, A. S. and Pickett, M. Shalet, D. (ed.) 2022. The epistemic insight digest: Issue 4: Spring 2022. Canterbury Canterbury Christ Church University.
Interdisciplinary engineering education - essential for the 21st century
Gordon, A., Simpson, S. and Hassanin, H. 2022. Interdisciplinary engineering education - essential for the 21st century.
Theoretical insights and quantitative prediction of the nature of boron–chalcogen (O, S, Se, Te) interactions using the electron density and the electron localisation function (ELF)
Michalski, M., Gordon, A. and Berski, S. 2021. Theoretical insights and quantitative prediction of the nature of boron–chalcogen (O, S, Se, Te) interactions using the electron density and the electron localisation function (ELF). Polyhedron. https://doi.org/10.1016/j.poly.2021.115495
In the search for ditriel B⋯Al non-covalent bonding
Berski, S. and Gordon, A. 2021. In the search for ditriel B⋯Al non-covalent bonding. New Journal of Chemistry . 45, pp. 16740-16749. https://doi.org/10.1039/D1NJ01963E
The nature of the triple Btriple bondB, double, Bdouble bondB, single, B–B, and one-electron, B.B boron-boron bonds from the topological analysis of electron localisation function (ELF) perspective
Mierzwa, G., Gordon, A.J. and Berski, S. 2020. The nature of the triple Btriple bondB, double, Bdouble bondB, single, B–B, and one-electron, B.B boron-boron bonds from the topological analysis of electron localisation function (ELF) perspective. Journal of Molecular Structure. 1221, p. 128530. https://doi.org/10.1016/j.molstruc.2020.128530
The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods
Mierzwa, G., Gordon, A.J. and Berski, S. 2020. The nature of multiple boron-nitrogen bonds studied using electron localization function (ELF), electron density (AIM), and natural bond orbital (NBO) methods. Journal of Molecular Modeling. 26 (136), pp. 1-23. https://doi.org/10.1007/s00894-020-04374-9
Epistemic insight: a systematic problem and an ecosystemic solution.
Nassaji, M. and Gordon, A.J. 2020. Epistemic insight: a systematic problem and an ecosystemic solution.
Topological analysis of the electron localisation function (ELF) applied to the electronic structure of oxaziridine: the nature of N-O bond
Michalski, M., Gordon, A.J. and Berski, S. 2019. Topological analysis of the electron localisation function (ELF) applied to the electronic structure of oxaziridine: the nature of N-O bond. Stuctural Chemistry. 30, pp. 2181-2189. https://doi.org/10.1007/s11224-019-01407-9
Topological analysis of electron localisation function: Unlocking the nature of B-C chemical bond. Possible existence of multiple bonds B@C and B„C
Mierzwa, G., Gordon, A.J. and Berski, S. 2019. Topological analysis of electron localisation function: Unlocking the nature of B-C chemical bond. Possible existence of multiple bonds B@C and B„C. Polyhedron. 170, pp. 180-187. https://doi.org/https://doi.org/10.1016/j.poly.2019.05.035
The nature of the T=T double bond (T = B, Al, Ga, In) in dialumene and its derivatives: topological study of the electron localization function (ELF)
Michalski, M., Gordon, A.J. and Berski, S. 2019. The nature of the T=T double bond (T = B, Al, Ga, In) in dialumene and its derivatives: topological study of the electron localization function (ELF). Journal of Molecular Modeling. 25, p. 211. https://doi.org/10.1007/s00894-019-4075-7
The electronic structure of molecules with the B F and B Cl bond in light of the topological analysis of electron localization function: Possibility of multiple bonds?
Mierzwa, G., Gordon, A.J. and Berski, S. 2018. The electronic structure of molecules with the B F and B Cl bond in light of the topological analysis of electron localization function: Possibility of multiple bonds? International Journal of Quantum Chemistry. 118, p. e25781. https://doi.org/10.1002/qua.25781
On the nature of the boron–copper interaction. Topological study of the electron localisation function (ELF)
Mierzwa, G., Gordon, A.J. and Berski, S. 2018. On the nature of the boron–copper interaction. Topological study of the electron localisation function (ELF). New Journal of Chemistry . 42, pp. 17096-17114. https://doi.org/10.1039/c8nj03516d
Characterisation of the reaction mechanism between ammonia and formaldehyde from the topological analysis of ELF and catastrophe theory perspective
Cmikiewicz, A., Gordon, A.J. and Berski, S. 2018. Characterisation of the reaction mechanism between ammonia and formaldehyde from the topological analysis of ELF and catastrophe theory perspective. Structural Chemistry. 29, pp. 243-255. https://doi.org/10.1007/s11224-017-1024-x
The nature of inter- and intramolecular interactions in F2OXe…HX (X= F, Cl, Br, I) complexes
Makarewicz, E., Lundell, J., Gordon, A.J. and Berski, S. 2016. The nature of inter- and intramolecular interactions in F2OXe…HX (X= F, Cl, Br, I) complexes. Journal of Molecular Modeling. 22 (119). https://doi.org/10.1007/s00894-016-2970-8
The electronic structure of the xenon insertion compounds XXe–MX2 (X = F, Cl, Br, I; M = B, Al, Ga)
Makarewicz, E., Gordon, A. and Berski, S. 2016. The electronic structure of the xenon insertion compounds XXe–MX2 (X = F, Cl, Br, I; M = B, Al, Ga). Polyhedron. 117, pp. 97-109. https://doi.org/10.1016/j.poly.2016.05.025
On the nature of interactions in the F2OXe…NCCH3 complex: Is there the Xe(IV)-N bond?
Makarewicz, E,, Lundell, J., Gordon, A.J. and Berski, S. 2016. On the nature of interactions in the F2OXe…NCCH3 complex: Is there the Xe(IV)-N bond? Journal of Computational Chemistry. 37 (20), pp. 1876-1886. https://doi.org/10.1002/jcc.24402
Diversity of the nature of the nitrogen-oxygen bond in inorganic and organic nitrites in the light of topological analysis of electron localisation function (ELF)
Berski, S. and Gordon, A. J. 2016. Diversity of the nature of the nitrogen-oxygen bond in inorganic and organic nitrites in the light of topological analysis of electron localisation function (ELF). in: Applications of Topological Methods in Molecular Chemistry https://link.springer.com/chapter/10.1007/978-3-319-29022-5_19 Springer. pp. 529-551
How many electrons form chemical bonds in the NgBeS (Ng = Ar, Kr, Xe) molecules? Topological study using the electron localisation function (ELF) and electron localisability indicator (ELI-D)
Makarewicz, E., Gordon, A.J. and Berski, S. 2016. How many electrons form chemical bonds in the NgBeS (Ng = Ar, Kr, Xe) molecules? Topological study using the electron localisation function (ELF) and electron localisability indicator (ELI-D). Structural Chemistry. 27, pp. 57-64. https://doi.org/10.1007/s11224-015-0719-0
Nature of the bonding in the AuNgX (Ng = Ar, Kr, Xe; X = F, Cl, Br, I) molecules. Topological study on electron density and the electron localization function (ELF)
Makarewicz, E., Gordon, A. J. and Berski, S. 2015. Nature of the bonding in the AuNgX (Ng = Ar, Kr, Xe; X = F, Cl, Br, I) molecules. Topological study on electron density and the electron localization function (ELF). Journal of Physical Chemistry A. 119 (11), p. 2401–2412. https://doi.org/10.1021/jp508266k
On the multiple B-O bonding using the topological analysis of electron localisation function (ELF)
Mierzwa, G., Gordon, A. J., Latajka, Z. and Berski, S. 2014. On the multiple B-O bonding using the topological analysis of electron localisation function (ELF). Computational and Theoretical Chemistry. 1053, pp. 130-141. https://doi.org/10.1016/j.comptc.2014.10.003