The impacts of benzoyl and benzyl groups on the non-covalent interactions and electronic properties of glycosyl acceptors

References

• Ghosh, B.; Kulkarni, S. S. Advances in Protecting Groups for Oligosaccharide Synthesis. Chem. Asian J. 2020, 15(4), 450–462. DOI: 10.1002/asia.201901621.
   PubMed Web of Science ®Google Scholar
• Li, R.; Yu, H.; Chen, X. Recent Progress in Chemical Synthesis of Bacterial Surface Glycans. Curr. Opin. Chem. Biol. 2020, 58, 121–136. DOI: 10.1016/j.cbpa.2020.08.003.
   PubMed Web of Science ®Google Scholar
• Witte, M. D.; Minnaard, A. J. Site-Selective Modification of (Oligo) Saccharides. ACS Catal. 2022, 12(19), 12195–12205. DOI: 10.1021/acscatal.2c03876.
   PubMed Web of Science ®Google Scholar
• Van Der Vorm, S.; Hansen, T.; Van Hengst, J. M.; Overkleeft, H. S.; Van Der Marel, G. A.; Codée, J. D. Acceptor Reactivity in Glycosylation Reactions. Chem. Soc. Rev. 2019, 48(17), 4688–4706. DOI: 10.1039/C8CS00369F.
   PubMed Web of Science ®Google Scholar
• Hettikankanamalage, A. A.; Lassfolk, R.; Ekholm, F. S.; Leino, R.; Crich, D. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions. Chem. Rev. 2020, 120(15), 7104–7151. DOI: 10.1021/acs.chemrev.0c00243.
   PubMed Web of Science ®Google Scholar
• Greis, K.; Leichnitz, S.; Kirschbaum, C.; Chang, C.; Lin, M.; Meijer, G.; von Helden, G.; Seeberger, P. H.; Pagel, K. The Influence of the Electron Density in Acyl Protecting Groups on the Selectivity of Galactose Formation. J. Am. Chem. Soc. 2022, 144(44), 20258–20266. DOI: 10.1021/jacs.2c05859.
   PubMed Web of Science ®Google Scholar
• McArdle, S.; Endo, S.; Aspuru-Guzik, A.; Benjamin, S. C.; Yuan, X. Quantum Computational Chemistry. Rev. Mod. Phys. 2020, 92(1), 015003. DOI: 10.1103/RevModPhys.92.015003.
   Web of Science ®Google Scholar
• Mikulak-Klucznik, B.; Gołębiowska, P.; Bayly, A. A.; Popik, O.; Klucznik, T.; Szymkuć, S.; Gajewska, E. P.; Dittwald, P.; Staszewska-Krajewska, O.; Beker, W.; et al. Computational Planning of the Synthesis of Complex Natural Products. Nature 2020, 588(7836), 83–88. DOI: 10.1038/s41586-020-2855-y.
   PubMed Web of Science ®Google Scholar
• de Almeida, A. F.; Moreira, R.; Rodrigues, T. Synthetic Organic Chemistry Driven by Artificial Intelligence. Nat. Rev. Chem. 2019, 3(10), 589–604. DOI: 10.1038/s41570-019-0124-0.
   Web of Science ®Google Scholar
• Elkin, M.; Newhouse, T. R. Computational Chemistry Strategies in Natural Product Synthesis. Chem. Soc. Rev. 2018, 47(21), 7830–7844. DOI: 10.1039/C8CS00351C.
   PubMed Web of Science ®Google Scholar
• Nakajima, M.; Adachi, Y.; Nemoto, T. Computation-Guided Asymmetric Total Syntheses of Resveratrol Dimers. Nat. Commun. 2022, 13(1), 152. DOI: 10.1038/s41467-021-27546-4.
   PubMed Web of Science ®Google Scholar
• Lassfolk, R.; Pedrón, M.; Tejero, T.; Merino, P.; Wärnå, J.; Leino, R. Acetyl Group Migration in Xylan and Glucan Model Compounds as Studied by Experimental and Computational Methods. J. Org. Chem. 2022, 87(21), 14544–14554. DOI: 10.1021/acs.joc.2c01956.
   PubMed Web of Science ®Google Scholar
• Hansen, T.; Elferink, H.; van Hengst, J. M. A.; Houthuijs, K. J.; Remmerswaal, W. A.; Kromm, A.; Berden, G.; van der Vorm, S.; Rijs, A. M.; Overkleeft, H. S.; et al. Characterization of Glycosyl Dioxolenium Ions and Their Role in Glycosylation Reactions. Nat. Commun. 2020, 11(1), 2664. DOI: 10.1038/s41467-020-16362-x.
   PubMed Web of Science ®Google Scholar
• Hansen, T.; Lebedel, L.; Remmerswaal, W. A.; van der Vorm, S.; Wander, D. P. A.; Somers, M.; Overkleeft, H. S.; Filippov, D. V.; Désiré, J.; Mingot, A.; et al. Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations. ACS Cent. Sci. 2019, 5(5), 781–788. DOI: 10.1021/acscentsci.9b00042.
   PubMed Web of Science ®Google Scholar
• Parr, R. G. Density Functional Theory. Annu. Rev. Phys. Chem. 1983, 34(1), 631–656. DOI: 10.1146/annurev.pc.34.100183.003215.
   Google Scholar
• Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Challenges for Density Functional Theory. Chem. Rev. 2012, 112(1), 289–320. DOI: 10.1021/cr200107z.
   PubMed Web of Science ®Google Scholar
• Rong, C.; Wang, B.; Zhao, D.; Liu, S. Information‐Theoretic Approach in Density Functional Theory and its Recent Applications to Chemical Problems. WIREs Comput. Mol. Sci. 2020, 10(4), e1461. DOI: 10.1002/wcms.1461.
   Google Scholar
• Te Vrugt, M.; Löwen, H.; Wittkowski, R. Classical Dynamical Density Functional Theory: from Fundamentals to Applications. Adv. Phys. 2020, 69(2), 121–247. DOI: 10.1021/cr200107z.
   Web of Science ®Google Scholar
• Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer. J. Comput. Chem. 2012, 33(5), 580–592. DOI: 10.1002/jcc.22885.
   PubMed Web of Science ®Google Scholar
• Yuan, Z.; Yin, T.; Zhang, D. Hybrid Quantum-Classical Algorithms for Solving Quantum Chemistry in Hamiltonian–Wave-Function Space. Phys. Rev. A. 2021, 103(1), 012413. DOI: 10.1103/PhysRevA.103.012413.
   Web of Science ®Google Scholar
• Pujal, L.; Tehrani, A.; Heidar-Zadeh, F. Conceptual Density Functional Theory; Wiley-VCH Verlag GmbH & Co: Baden-Württemberg, Germany, 2022; pp 649–661.
   Google Scholar
• Murray, J. S.; Politzer, P. The electrostatic potential: an overview. Wiley Interdiscip. Rev.: Comput. Mol. Sci 2011, 1, 153–163. DOI: 10.1002/wcms.19.
   Web of Science ®Google Scholar
• Suresh, C. H.; Remya, G. S.; Anjalikrishna, P. K. Molecular Electrostatic Potential Analysis: A Powerful Tool to Interpret and Predict Chemical Reactivity. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2022, 12(5), e1601. DOI: 10.1002/wcms.1601.
   Web of Science ®Google Scholar
• Tanaka, K.; Chujo, Y. New idea for narrowing an energy gap by selective perturbation of one frontier molecular orbital. Chem. Lett. 2021, 50(2), 269–279. DOI: 10.1246/cl.200756.
   Web of Science ®Google Scholar
• Seeman, J. I. Kenichi Fukui, Frontier Molecular Orbital Theory, and the Woodward‐Hoffmann Rules. Part I. The Person. Chem. Rec. 2022, 22(4), e202100297. DOI: 10.1002/tcr.202100297.
   PubMed Web of Science ®Google Scholar
• Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García, J.; Cohen, A. J.; Yang, W. Revealing Noncovalent Interactions. J. Am. Chem. Soc. 2010, 132(18), 6498–6506. DOI: 10.1021/ja100936w.
   PubMed Web of Science ®Google Scholar
• Seeman, J. I. Effect of Conformational Change on Reactivity in Organic Chemistry. Evaluations, Applications, and Extensions of Curtin-Hammett Winstein-Holness Kinetics. Chem. Rev. 1983, 83(2), 83–134. DOI: 10.1021/cr00054a001.
   Web of Science ®Google Scholar
• Brink, B. D.; DeFrancisco, J. R.; Hillner, J. A.; Linton, B. R. Curtin–Hammett and Steric Effects in HOBt Acylation Regiochemistry. J. Org. Chem. 2011, 76(13), 5258–5263. DOI: 10.1021/jo200346r.
   PubMed Web of Science ®Google Scholar
• Seeman, J. I. The Curtin-Hammett Principle and the Winstein-Holness Equation: New Definition and Recent Extensions to Classical Concepts. J. Chem. Educ. 1986, 63(1), 42. DOI: 10.1021/ed063p42.
   Web of Science ®Google Scholar
• Qin, C.; Li, L.; Tian, G.; Ding, M.; Zhu, S.; Song, W.; Hu, J.; Seeberger, P. H.; Yin, J. Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4, 6-O-Pyruvyl Ketal. J. Am. Chem. Soc. 2022, 144(46), 21068–21079. DOI: 10.1021/jacs.2c05953.
   PubMed Web of Science ®Google Scholar
• Lu, T.; Chen, Q. Independent Gradient Model Based on Hirshfeld Partition: A New Method for Visual Study of Interactions in Chemical Systems. J. Comput. Chem. 2022, 43(8), 539–555. DOI: 10.1002/jcc.26812.
   PubMed Web of Science ®Google Scholar
• Lu, T.; Chen, Q. Visualization Analysis of Weak Interactions in Chemical Systems. In Comprehensive Computational Chemistry, First edition; Yáñez, M., Boyd, R. J., Eds.; Elsevier: Oxford, 2024; pp 240–264.
   Google Scholar
• Lu, T.; Chen, Q. Interaction Region Indicator: A Simple Real Space Function Clearly Revealing Both Chemical Bonds and Weak Interactions. Chem. Methods. 2021, 1(5), 231–239.
   Google Scholar
• Murray, J. S.; Politzer, P. Electrostatic Potentials: Chemical Applications; Wiley-VCH Verlag GmbH & Co: Baden-Württemberg, Germany, 1998.
   Google Scholar
• Politzer, P.; Murray, J. S.; Bulat, F. A. Average Local Ionization Energy: A Review. J. Mol. Model. 2010, 16(11), 1731–1742. DOI: 10.1007/s00894-010-0709-5.
   PubMed Web of Science ®Google Scholar
• Lu, T.; Chen, F. Atomic Dipole Moment Corrected Hirshfeld Population Method. J. Theor. Comput. Chem. 2012, 11(01), 163–183. DOI: 10.1142/S0219633612500113.
   Web of Science ®Google Scholar
• Hohenstein, E. G.; Chill, S. T.; Sherrill, C. D. Assessment of the Performance of the M05-2X and M06-2X Exchange-Correlation Functionals for Noncovalent Interactions in Biomolecules. J. Chem. Theory Comput. 2008, 4(12), 1996–2000. DOI: 10.1021/ct800308k.
   PubMed Web of Science ®Google Scholar
• Walker, M.; Harvey, A. J.; Sen, A.; Dessent, C. E. Performance of M06, M06-2X, and M06-HF Density Functionals for Conformationally Flexible Anionic Clusters: M06 Functionals Perform Better than B3LYP for a Model System with Dispersion and Ionic Hydrogen-Bonding Interactions. J. Phys. Chem. A. 2013, 117(47), 12590–12600. DOI: 10.1021/jp408166m.
   PubMed Web of Science ®Google Scholar
• Pauling, L. The Nature of the Chemical Bond; Cornell: Ithaca, New York, 1960, p 350.
   Google Scholar
• Tang, T.-H.; Deretey, E.; Knak Jensen, S.; Csizmadia, I. Hydrogen Bonds: Relation Between Lengths and Electron Densities at Bond Critical Points. Eur. Phys. J. D. 2006, 37(2), 217–222. DOI: 10.1140/epjd/e2005-00317-0.
   Web of Science ®Google Scholar
• Crabtree, R. H. A new type of hydrogen bond. Science. 1998, 282(5396), 2000–2001. DOI: 10.1126/science.282.5396.2000.
   Web of Science ®Google Scholar
• Steiner, T. The Hydrogen Bond in the Solid State. Angew. Chem. Int. Ed. 2002, 41(1), 48–76. DOI: 10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U.
   Web of Science ®Google Scholar
• Andersson, Y.; Hult, E.; Rydberg, H.; Apell, P.; Lundqvist, B. I.; Langreth, D. C. Electronic Density Functional Theory; Springer: Boston, MA, 1998; pp 243–260.
   Google Scholar
• Hermann, J.; DiStasio, R. A.; Jr.; Tkatchenko, A. First-Principles Models for van der Waals Interactions in Molecules and Materials: Concepts, Theory, and Applications. Chem. Rev. 2017, 117(6), 4714–4758. DOI: 10.1021/acs.chemrev.6b00446.
   PubMed Web of Science ®Google Scholar
• Hibbert, F.; Emsley, J. Hydrogen Bonding and Chemical Reactivity. Adv. Phys. Org. Chem. 1990, 26, 255–379.
   Google Scholar
• Politzer, P.; Murray, J. S. Molecular Electrostatic Potentials and Chemical Reactivity. Rev. Comput. Chem. 1991, 2, 273–312.
   Google Scholar
• Coulson, C. A.; Longuet-Higgins, H. C. The Electronic Structure of Conjugated Systems I. General Theory. Proc. R. Soc. London. Sect. A. Math. Phys. Sci. 1947, 191(1024), 39–60. DOI: 10.1098/rspa.1947.0102.
   PubMedGoogle Scholar
• Longuet-Higgins, H.; Murrell, J. The Electronic Spectra of Aromatic Molecules V: The Interaction of Two Conjugated Systems. Proc. Phys. Soc. A. 1955, 68(7), 601–611. DOI: 10.1088/0370-1298/68/7/308.
   Google Scholar
• Politzer, P.; Murray, J. Chemical Reactivity Theory: A Density Functional View; CRC Press LLC: Boca Raton, FL, 2009; pp 243–254.
   Google Scholar
• Liu, L. L.; Stephan, D. W. Radicals Derived from Lewis Acid/Base Pairs. Chem. Soc. Rev. 2019, 48(13), 3454–3463. DOI: 10.1039/C8CS00940F.
   PubMed Web of Science ®Google Scholar
• Liu, Z.; Lu, T.; Chen, Q. Intermolecular Interaction Characteristics of the All-Carboatomic Ring, Cyclo [18] Carbon: Focusing on Molecular Adsorption and Stacking. Carbon. 2021, 171, 514–523. DOI: 10.1016/j.carbon.2020.09.048.
   Web of Science ®Google Scholar
• Singha, M.; Bhattacharya, P.; Ray, D.; Basak, A. Sterically Hindering the Trajectory of Nucleophilic Attack Towards p-Benzynes by a Properly Oriented Hydrogen Atom: An Approach to Achieve Regioselectivity. Org. Biomol. Chem. 2021, 19(23), 5148–5154. DOI: 10.1039/D1OB00521A.
   PubMed Web of Science ®Google Scholar
• Neuvonen, H.; Neuvonen, K.; Pasanen, P. Evidence of Substituent-Induced Electronic Interplay. Effect of the Remote Aromatic Ring Substituent of Phenyl Benzoates on the Sensitivity of the Carbonyl Unit to Electronic Effects of Phenyl or Benzoyl Ring Substituents. J. Org. Chem. 2004, 69(11), 3794–3800. DOI: 10.1021/jo035521u.
   PubMed Web of Science ®Google Scholar
• Toro-Labbé, A. Theoretical Aspects of Chemical Reactivity; Elsevier: Amsterdam Netherlands, 2006.
   Google Scholar
• Fu Lu T.; Chen, F. 北京科技大学化学与生物工程学院化学与化学工程系, 北京100083, Department of Chemistry and Chemical Engineering, School of Chemical and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, P. R. China Comparing Methods for Predicting the Reactive Site of Electrophilic Substitution. Acta Phys. Chim. Sin. 2014, 30(4), 628–639. DOI: 10.3866/PKU.WHXB201401211.
   Web of Science ®Google Scholar
• Al-Zaqri, N.; Pooventhiran, T.; Alsalme, A.; Rao, D. J.; Rao, S. S.; Sankar, A.; Thomas, R. First-Principle Studies of Istradefylline with Emphasis on the Stability, Reactivity, Interactions and Wavefunction-Dependent Properties. Polycyclic Aromat. Compd. 2022, 42(6), 3238–3252. DOI: 10.1080/10406638.2020.1857273.
   Web of Science ®Google Scholar
• Pooventhiran, T.; Bhattacharyya, U.; Rao, D. J.; Chandramohan, V.; Karunakar, P.; Irfan, A.; Mary, Y. S.; Thomas, R. Detailed Spectra, Electronic Properties, Qualitative Non-Covalent Interaction Analysis, Solvatochromism, Docking and Molecular Dynamics Simulations in Different Solvent Atmosphere of Cenobamate. Struct. Chem. 2020, 31(6), 2475–2485. DOI: 10.1007/s11224-020-01607-8.
   Web of Science ®Google Scholar
• Pooventhiran, T.; Cheriet, M.; Bhattacharyya, U.; Irfan, A.; Puchta, R.; Sowrirajan, S.; Thomas, R. Detailed Structural Examination, Quantum Mechanical Studies of the Aromatic Compound Solarimfetol and Formation of Inclusion Compound with Cucurbituril. Polycyclic Aromat. Compd. 2022, 42(8), 5443–5455. DOI: 10.1080/10406638.2021.1937238.
   Web of Science ®Google Scholar
• Zhu, S.; Khan, M. A.; Wang, F.; Bano, Z.; Xia, M. Rapid Removal of Toxic Metals Cu2+ and Pb2+ by Amino Trimethylene Phosphonic Acid Intercalated Layered Double Hydroxide: A Combined Experimental and DFT Study. Chem. Eng. J. 2020, 392, 123711. DOI: 10.1016/j.cej.2019.123711.
   Web of Science ®Google Scholar
• Heuckendorff, M.; Pedersen, C. M.; Bols, M. Quantifying Electronic Effects of Common Carbohydrate Protecting Groups in a Piperidine Model System. Chemistry. 2010, 16(47), 13982–13994. DOI: 10.1002/chem.201002313.
   PubMed Web of Science ®Google Scholar
• Mulliken, R. S. Electronic Population Analysis on LCAO–MO Molecular Wave Functions. I. J. Chem. Phys. 1955, 23(10), 1833–1840. DOI: 10.1063/1.1740588.
   Web of Science ®Google Scholar
• Edmiston, C.; Ruedenberg, K. Localized Atomic and Molecular Orbitals. Rev. Mod. Phys. 1963, 35(3), 457–464. DOI: 10.1103/RevModPhys.35.457.
   Web of Science ®Google Scholar
• Spackman, M. A.; Jayatilaka, D. Hirshfeld Surface Analysis. CrystEngComm. 2009, 11(1), 19–32. DOI: 10.1039/B818330A.
   Web of Science ®Google Scholar
• Lu.; Chen, F. 北京科技大学化学与生物工程学院, 北京 100083, School of Chemical and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, P. R. China. Comparison of Computational Methods for Atomic Charges. Acta Phys. Chim. Sin. 2012, 28(01), 1–18. DOI: 10.3866/PKU.WHXB2012281.
   Google Scholar
• Cao, J.; Ren, Q.; Chen, F.; Lu, T. Comparative Study on the Methods for Predicting the Reactive Site of Nucleophilic Reaction. Sci. China Chem. 2015, 58(12), 1845–1852. DOI: 10.1007/s11426-015-5494-7.
   Web of Science ®Google Scholar
• Whitfield, D. M.; Guo, J. Proton Transfer and Hydrogen Bonding in Glycosylation Reactions. J. Carbohydr. Chem. 2017, 36(2–3), 59–99. DOI: 10.1080/07328303.2017.1365369.
   Web of Science ®Google Scholar
• Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. How Does the Electronegativity of the Substituent Dictate the Strength of the Gauche Effect? J. Am. Chem. Soc. 1994, 116(9), 4038–4043. DOI: 10.1021/ja00088a043.
   Web of Science ®Google Scholar
• Los, J.; Geerlings, J. J. C. Charge Exchange in Atom-Surface Collisions. Phys. Rep. 1990, 190(3), 133–190. DOI: 10.1016/0370-1573(90)90104-a.
   Google Scholar
• Pamperin, M.; Bronold, F.; Fehske, H. Mixed-Valence Correlations in Charge-Transferring Atom–Surface Collisions. Phys. Scr. 2015, T165, 014008. DOI: 10.1088/0031-8949/2015/T165/014008.
   Web of Science ®Google Scholar
• Obu, Q. S.; Louis, H.; Odey, J. O.; Eko, I. J.; Abdullahi, S.; Ntui, T. N.; Offiong, O. E. Synthesis, Spectra (FT-IR, NMR) Investigations, DFT Study, In Silico ADMET and Molecular Docking Analysis of 2-Amino-4-(4-Aminophenyl) Thiophene-3-Carbonitrile as a Potential Anti-Tubercular Agent. J. Mol. Struct. 2021, 1244, 130880. DOI: 10.1016/j.molstruc.2021.130880.
   Web of Science ®Google Scholar
• Mishma, J. C.; Jothy, V. B.; Muthu, S.; Irfan, A. Bonding Nature, Nucleophilic Reactivity and Electron Excitation of NLO Active 2, 6 Dichloroindophenol Sodium Salt (Polar and Non Polar Solvents) with Topology Analysis-Bacterial Pathogens Study. J. Mol. Liq. 2022, 367, 120533. DOI: 10.1016/j.molliq.2022.120533.
   Web of Science ®Google Scholar
• Braga, L. S.; Leal, D. H.; Kuca, K.; Ramalho, T. C. Perspectives on the Role of the Frontier Effective-For-Reaction Molecular Orbital (FERMO) in the Study of Chemical Reactivity: An Updated Review. Coc. 2020, 24(3), 314–331. DOI: 10.2174/1385272824666200204121044.
   Google Scholar
• Bulat, F. A.; Chamorro, E.; Fuentealba, P.; Toro-Labbé, A. Condensation of Frontier Molecular Orbital Fukui Functions. J. Phys. Chem. A. 2004, 108(2), 342–349. DOI: 10.1021/jp036416r.
   Web of Science ®Google Scholar
• Khemalapure, S. S.; Katti, V. S.; Hiremath, C. S.; Hiremath, S. M.; Basanagouda, M.; Radder, S. B. Spectroscopic (FT-IR, FT-Raman, NMR and UV-Vis), ELF, LOL, NBO, and Fukui Function Investigations on (5-Bromo-Benzofuran-3-yl)-Acetic Acid Hydrazide (5BBAH): Experimental and Theoretical Approach. J. Mol. Struct. 2019, 1196, 280–290. DOI: 10.1016/j.molstruc.2019.06.078.
   Web of Science ®Google Scholar
• Houk, K. N. Frontier Molecular Orbital Theory of Cycloaddition Reactions. Acc. Chem. Res. 1975, 8(11), 361–369. DOI: 10.1021/ar50095a001.
   Web of Science ®Google Scholar
• Fukui, K. Role of Frontier Orbitals in Chemical Reactions. Science. 1982, 218(4574), 747–754. DOI: 10.1126/science.218.4574.747.
   PubMed Web of Science ®Google Scholar
• Rauk, A. Orbital Interaction Theory of Organic Chemistry; John Wiley & Sons: New York, 2004.
   Google Scholar
• Dewar, M. J. Aromaticity and Pericyclic Reactions. Angew. Chem. Int. Ed. Engl. 1971, 10(11), 761–776. DOI: 10.1002/anie.197107611.
   Web of Science ®Google Scholar
• Oda, A.; Ohkubo, T.; Yumura, T.; Kobayashi, H.; Kuroda, Y. Room-Temperature Activation of the C–H Bond in Methane over Terminal ZnII–Oxyl Species in an MFI Zeolite: A Combined Spectroscopic and Computational Study of the Reactive Frontier Molecular Orbitals and their Origins. Inorg. Chem. 2018, 58(1), 327–338. DOI: 10.1021/acs.inorgchem.8b02425.
   PubMed Web of Science ®Google Scholar
• Yu, J.; Su, N. Q.; Yang, W. Describing Chemical Reactivity with Frontier Molecular Orbitalets. JACS Au. 2022, 2(6), 1383–1394. DOI: 10.1021/jacsau.2c00085.
   PubMedGoogle Scholar
• Frisch, M.; Trucks, G.; Schlegel, H. B.; Scuseria, G.; Robb, M.; Cheeseman, J.; Scalmani, G.; Barone, V.; Petersson, G.; Nakatsuji, H. Gaussian 16; Gaussian, Inc.: Wallingford, CT, 2016.
   Google Scholar
• Humphrey, W.; Dalke, A.; Schulten, K. VMD: visual molecular dynamics. J. Mol. Graph. 1996, 14(1), 33–38. DOI: 10.1016/0263-7855(96)00018-5.
   PubMedGoogle Scholar
• Williams, T.; Kelley, C.; Bersch, C.; Bröker, H.-B.; Campbell, J.; Cunningham, R.; Denholm, D.; Elber, G.; Fearick, R.; Grammes, C. Gnuplot 5.2.; Alogus Publishing: New York, 2017.
   Google Scholar
• Legault, C. Y. CYLview 20; niversité de Sherbrooke: Fredericton, 2020.
   Google Scholar