{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T01:12:56Z","timestamp":1783041176466,"version":"3.54.6"},"reference-count":50,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2024,11,6]],"date-time":"2024-11-06T00:00:00Z","timestamp":1730851200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan","award":["AP14871058"],"award-info":[{"award-number":["AP14871058"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The supramolecular structure of the crystal products\u2013N-[2-chloro-2-(silatranyl)ethyl]-4-nitro-benzenesulfonamide 4d and N-chloro-N-[2-chloro-1-(silatran-1-yl-methyl)ethyl]benzene-sulfonamide 5a was established by X-ray diffraction analysis data, FTIR spectroscopy and DFT quantum chemical calculations. Their crystal lattice is formed by cyclic dimers with intermolecular hydrogen NH\u2219\u2219\u2219O-Si bonds and CH\u2219\u2219\u2219O=S short contacts. The distribution of electron density in the monomers was determined using quantum chemical calculations of their molecular electrostatic potential (MESP) in an isolated state (in gas) and in a polar medium. The transition from covalent N\u2013Si bonds in crystal compounds and polar medium to non-covalent N\u2219\u2219\u2219Si bonds happened while performing the calculations on the monomer molecules and their dimers in gas. The effect of intermolecular interactions on the strength of the N\u2013Si and N\u2219\u2219\u2219Si bonds in molecules was evaluated through calculations of their complexes with H2O and DMSO.<\/jats:p>","DOI":"10.3390\/ijms252211920","type":"journal-article","created":{"date-parts":[[2024,11,6]],"date-time":"2024-11-06T06:27:39Z","timestamp":1730874459000},"page":"11920","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Supramolecular Structure of Sulfonamide-Substituted Silatranes: Quantum Chemical DFT Calculations"],"prefix":"10.3390","volume":"25","author":[{"given":"Nina N.","family":"Chipanina","sequence":"first","affiliation":[{"name":"A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sergey N.","family":"Adamovich","sequence":"additional","affiliation":[{"name":"A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arailym M.","family":"Nalibayeva","sequence":"additional","affiliation":[{"name":"D.V. Sokolsky Institute of Fuel, Catalysis and Electrochemistry, 142 Kunayev Street, Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yerlan N.","family":"Abdikalykov","sequence":"additional","affiliation":[{"name":"D.V. Sokolsky Institute of Fuel, Catalysis and Electrochemistry, 142 Kunayev Street, Almaty 050010, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Larisa P.","family":"Oznobikhina","sequence":"additional","affiliation":[{"name":"A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elizaveta N.","family":"Oborina","sequence":"additional","affiliation":[{"name":"A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Igor B.","family":"Rozentsveig","sequence":"additional","affiliation":[{"name":"A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,11,6]]},"reference":[{"key":"ref_1","unstructured":"Lee, V.Y. (2017). Chapter 11\u2014Penta- and Hexacoordinated Silicon(IV) Compounds. Organosilicon Compounds, Theory and Experiment (Synthesis), Academic Press."},{"key":"ref_2","first-page":"1727","article-title":"Hypervalent Silicon as a Reactive Site in Selective Bond-Forming Processes","volume":"11","author":"Rendler","year":"2005","journal-title":"Synthesis"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"492","DOI":"10.1016\/j.ccr.2007.10.009","article-title":"Stereoselective Reactions Involving Hypervalent Silicate Complexes","volume":"252","author":"Benaglia","year":"2008","journal-title":"Coord. Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"848","DOI":"10.1070\/RC2014v083n09ABEH004385","article-title":"Synthesis, properties and reactivity of intramolecular hypercoordinate silicon complexes","volume":"83","author":"Nikolin","year":"2014","journal-title":"Russ. Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1070\/RCR4466","article-title":"Coordination compounds of tetravalent silicon, germanium and tin: The structure, chemical bonding and intermolecular interactions in them","volume":"84","author":"Korlyukov","year":"2015","journal-title":"Russ. Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1791","DOI":"10.1039\/B925899J","article-title":"Silatranes: A Review on their Synthesis, Structure, Reactivity and Applications","volume":"40","author":"Puri","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"e4940","DOI":"10.1002\/aoc.4940","article-title":"New atranes and similar ionic complexes. Synthesis, structure, properties","volume":"33","author":"Adamovich","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1330","DOI":"10.1007\/s10593-012-0918-1","article-title":"Basicity of silatranes (Review)","volume":"47","author":"Voronkov","year":"2012","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1023\/B:PHAC.0000027635.41154.0d","article-title":"Antitumor Activity of Silatranes (A Review)","volume":"38","author":"Voronkov","year":"2004","journal-title":"Pharm. Chem. J."},{"key":"ref_10","unstructured":"Tolstikov, G.A. (2005). Use of Silatranes for Medicine and Agriculture, Publishing House of the Siberian Branch of Russian Academy of Sciences."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"514","DOI":"10.1134\/S1019331610060079","article-title":"Atranes As a New Generation of Biologically Active Substances","volume":"80","author":"Voronkov","year":"2010","journal-title":"Her. Russ. Acad. Sci."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"e5976","DOI":"10.1002\/aoc.5976","article-title":"Isoxazole derivatives of silatrane: Synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action","volume":"34","author":"Adamovich","year":"2020","journal-title":"Appl. Organomet. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Adamovich, S.N., Oborina, E.N., Nalibayeva, A.M., and Rozentsveig, I.B. (2022). 3-Aminopropylsilatrane and Its Derivatives: A Variety of Applications. Molecules, 27.","DOI":"10.3390\/molecules27113549"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Adamovich, S.N., Ushakov, I.A., Oborina, E.N., Lukyanova, S.V., and Komarov, V.Y. (2023). New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24129965"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Hussein, E.M., Al-Rooqi, M.M., Abd El-Galil, S.M., and Ahmed, S.A. (2019). Design, synthesis, and biological evaluation of novel N4-substituted sulfonamides: Acetamides derivatives as dihydrofolate reductase (DHFR) inhibitors. BMC Chem., 13.","DOI":"10.1186\/s13065-019-0603-x"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1016\/j.ejmech.2016.08.039","article-title":"Hybrid molecules: The privileged scaffolds for various Pharmaceuticals","volume":"124","author":"Shaveta","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"122150","DOI":"10.1016\/j.jorganchem.2021.122150","article-title":"Silatrane-sulfonamide hybrids: Synthesis, characterization, and evaluation of biological activity","volume":"957","author":"Adamovich","year":"2022","journal-title":"J. Organomet. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1007\/s00894-019-3962-2","article-title":"\u03c3-Holes and Si\u00b7\u00b7\u00b7N intramolecular interactions","volume":"25","author":"Murray","year":"2019","journal-title":"J. Mol. Model."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2550","DOI":"10.1021\/acs.jpca.7b12357","article-title":"Crowding in Tetrel Bonds","volume":"122","author":"Scheiner","year":"2018","journal-title":"J. Phys. Chem. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1007\/s00214-017-2069-z","article-title":"A theoretical study of the HnF4\u2212nSi:N-base (n = 1\u20134) tetrel-bonded complexes","volume":"136","author":"Alkorta","year":"2017","journal-title":"Theor. Chem. Acc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1039\/D2CE01621D","article-title":"The Tetrel Bond: Definition of the Tetrel Bond","volume":"25","author":"Varadwaj","year":"2023","journal-title":"CrystEngComm"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1021\/cr9900331","article-title":"Noncovalent Interactions: A Challenge for Experiment and Theory","volume":"100","author":"Hobza","year":"2000","journal-title":"Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"12317","DOI":"10.1002\/anie.201306501","article-title":"Tetrel-Bonding Interaction: Rediscovered Supramolecular Force?","volume":"52","author":"Mooibroek","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.ccr.2019.01.003","article-title":"Tetrel Bonding Interactions at Work: Impact on Tin and Lead Coordination Compounds","volume":"384","author":"Seth","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1002\/wcms.1113","article-title":"\u03c3-Holes","volume":"3","author":"Clark","year":"2013","journal-title":"WIREs Comput. Mol. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"17238","DOI":"10.1039\/C4CP01775G","article-title":"Significant evidence of C\u2219\u2219\u2219O and C\u2219\u2219\u2219C long-range contacts in several heterodimeric complexes of CO with CH3\u2013X, should one refer to them as carbon and dicarbon bonds","volume":"16","author":"Varadwaj","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"14884","DOI":"10.1039\/C7CP02518A","article-title":"Tetrel, pnictogen and chalcogen bonds identified in the gas phase before they had names: A systematic look at non-covalent interactions","volume":"19","author":"Legon","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"e202400410","DOI":"10.1002\/cphc.202400410","article-title":"The Rivalry between Intramolecular Tetrel Bonds and Intermolecular Hydrogen Bonds in (O\u2013Si) Chelates of N-Silylmethylamides and -ureas. A Theoretical Study","volume":"25","author":"Chipanina","year":"2024","journal-title":"Chem. Phys. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1021\/jp002808b","article-title":"Molecular complexes between silicon derivatives and electron-rich groups","volume":"105","author":"Alkorta","year":"2001","journal-title":"J. Phys. Chem. A"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3119","DOI":"10.1039\/C2CE26393A","article-title":"Sensitivity of noncovalent bonds to intermolecular separation: Hydrogen, halogen, chalcogen, and pnicogen bonds","volume":"15","author":"Scheiner","year":"2013","journal-title":"CrystEngComm"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1021\/ar3001316","article-title":"The pnicogen bond: Its relation to hydrogen, halogen, and other noncovalent bonds","volume":"46","author":"Scheiner","year":"2013","journal-title":"Acc. Chem. Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"e202300326","DOI":"10.1002\/cphc.202300326","article-title":"Comparison of the Ability of N-Bases to Engage in Noncovalent Bonds","volume":"24","author":"Amonov","year":"2023","journal-title":"Chem. Phys. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"112153","DOI":"10.1016\/j.chemphys.2023.112153","article-title":"Silatranes: Relationship between the experimental Si \u2192 N dative bond length and its calculated energy according to AIM analysis data","volume":"578","author":"Sterkhova","year":"2024","journal-title":"Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2832","DOI":"10.1039\/b801115j","article-title":"Covalent radii revisited","volume":"21","author":"Cordero","year":"2008","journal-title":"Dalton Trans."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Romanovs, V., Belyakov, S., Doronina, E., Sidorkin, V., Roisnel, T., and Jouikov, V. (2023). Crystal Structure of New 1-Phenyl-Substituted Tribenzsilatranes. Crystals, 13.","DOI":"10.3390\/cryst13050772"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1002\/tcr.201500256","article-title":"Tetrel Bonding Interactions","volume":"16","author":"Mooibroek","year":"2016","journal-title":"Chem. Rec."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/j100785a001","article-title":"Van der Waals radius","volume":"68","author":"Bondi","year":"1964","journal-title":"J. Phys. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0022-328X(00)86939-9","article-title":"Silatranes","volume":"233","author":"Voronkov","year":"1982","journal-title":"J. Organomet. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2373","DOI":"10.1134\/S1070363221120033","article-title":"Theoretical Analysis of the Reactivity of N-[2-Bromo-2-(trimethylsilyl)ethyl]sulfonamides and Their Self-Association","volume":"91","author":"Oznobikhina","year":"2021","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2305","DOI":"10.1002\/cphc.202100612","article-title":"Enhancement of the Tetrel Bond by the Effects of Substituents, Cooperativity, and Electric Field: Transition from Noncovalent to Covalent Bond","volume":"22","author":"Liu","year":"2021","journal-title":"ChemPhysChem"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1289\/ehp.8561191","article-title":"Molecular electrostatic potentials: An effective tool for the elucidation of biochemical phenomena","volume":"61","author":"Politzer","year":"1985","journal-title":"Environ. Health Perspect."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"128534","DOI":"10.1016\/j.molstruc.2020.128534","article-title":"New oxyalkyl derivatives of trifluoromethanesulfonamide: Dynamic rivalry between different types of chain and cyclic associates in different phase states","volume":"1219","author":"Chipanina","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Bader, R.F.W. (1990). Atoms in Molecules, a Quantum Theory, Clarendon Press.","DOI":"10.1093\/oso\/9780198551683.001.0001"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/S0009-2614(98)00036-0","article-title":"Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities","volume":"285","author":"Espinosa","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref_45","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2013). Gaussian 09 Software, Gaussian Inc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2762","DOI":"10.1039\/D0CP05872F","article-title":"The hierarchy of ab initio and DFT methods for describing an intramolecular non-covalent Si\u2219\u2219\u2219N contact in the silicon compounds using electron diffraction geometries","volume":"23","author":"Belogolova","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1021\/ar200255p","article-title":"Calculations on noncovalent interactions and databases of benchmark interaction energies","volume":"17","author":"Hobza","year":"2012","journal-title":"Acc. Chem. Res."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1002\/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-Y","article-title":"AIM2000","volume":"22","author":"Schonbohm","year":"2001","journal-title":"J. Comput. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5178","DOI":"10.1021\/acs.jpca.9b03876","article-title":"Tetrel Bonding along the Pathways of Transsilylation and Alkylation of N-Trimethylsilyl-N-methylacetamide with Bifunctional (Chloromethyl)fluorosilanes","volume":"123","author":"Chipanina","year":"2019","journal-title":"J. Phys. Chem. A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/22\/11920\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:27:11Z","timestamp":1760113631000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/22\/11920"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,6]]},"references-count":50,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2024,11]]}},"alternative-id":["ijms252211920"],"URL":"https:\/\/doi.org\/10.3390\/ijms252211920","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,6]]}}}