Skip to main content

2022 | OriginalPaper | Buchkapitel

7. Supramolecular Assemblies Based on σ-hole Interactions

verfasst von : Antonio Bauzá, Antonio Frontera

Erschienen in: Supramolecular Assemblies Based on Electrostatic Interactions

Verlag: Springer International Publishing

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Elements belonging to Groups 14–17 and Periods 3–6 frequently act as Lewis acids which are able to establish directional noncovalent interactions (NCI) with a variety of Lewis bases (lone pair donors), π-systems (aromatic rings, triple and double bonds) and non-nucleophilic anions (BF4, PF6, ClO4, etc.). These promising NCIs are named in general as σ-hole interactions that are subdivided as tetrel bonds for elements belonging to group 14, pnictogen bonding for group 15, chalcogen bonding for group 16, and halogen bonding for group 17. In general, σ-hole interactions offer differentiating features when moving down in the same group (larger and more positive σ-holes) or moving left in the same row (number of available σ-holes and directionality) of the periodic table. This chapter shows that Molecular Electrostatic Potential (MEP) surface calculation is a powerful tool to explain the solid-state architecture of many X-ray structures. This is exemplified by using many examples retrieved from the Cambridge Structural Database (CSD), especially focused on σ-hole interactions.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
32.
Zurück zum Zitat Metrangolo P, Resnati G (eds) (2008) Halogen bonding: fundamentals and applications. Springer, Berlin Metrangolo P, Resnati G (eds) (2008) Halogen bonding: fundamentals and applications. Springer, Berlin
37.
Zurück zum Zitat Metrangolo P, Resnati G (eds) (2015) Halogen bonding II Impact on materials chemistry and life sciences. Springer International Publishing AG, Heidelberg Metrangolo P, Resnati G (eds) (2015) Halogen bonding II Impact on materials chemistry and life sciences. Springer International Publishing AG, Heidelberg
44.
Zurück zum Zitat del Bene JE, Alkorta I, Elguero J (2015) The pnicogen bond in review: structures, binding energies, bonding properties, and spin–spin coupling constants of complexes stabilized by pnicogen bonds. In: Scheiner S (ed) Noncovalent forces. Springer, Heidelberg, pp 191–264. https://doi.org/10.1007/978-3-319-14163-3_8 del Bene JE, Alkorta I, Elguero J (2015) The pnicogen bond in review: structures, binding energies, bonding properties, and spin–spin coupling constants of complexes stabilized by pnicogen bonds. In: Scheiner S (ed) Noncovalent forces. Springer, Heidelberg, pp 191–264. https://​doi.​org/​10.​1007/​978-3-319-14163-3_​8
48.
Zurück zum Zitat Priimagi A, Cavallo G, Forni A, Gorynsztejn-Leben M, Kaivola M, Metrangolo P, Milani R, Shishido A, Pilati T, Resnati G, Terraneo G (2012) Halogen bonding versus hydrogen bonding in driving self-assembly and performance of light-responsive supramolecular polymers. Adv Funct Mater 22:2572–2579. https://doi.org/10.1002/adfm.201200135CrossRef Priimagi A, Cavallo G, Forni A, Gorynsztejn-Leben M, Kaivola M, Metrangolo P, Milani R, Shishido A, Pilati T, Resnati G, Terraneo G (2012) Halogen bonding versus hydrogen bonding in driving self-assembly and performance of light-responsive supramolecular polymers. Adv Funct Mater 22:2572–2579. https://​doi.​org/​10.​1002/​adfm.​201200135CrossRef
77.
Zurück zum Zitat Huta OM, Patsaj IO, Konitz A, Meszko J, Blazejowski J (2002) 9-Cyano-10-methylacridinium hydrogen dinitrate. Acta Cryst C58:o295–o297 Huta OM, Patsaj IO, Konitz A, Meszko J, Blazejowski J (2002) 9-Cyano-10-methylacridinium hydrogen dinitrate. Acta Cryst C58:o295–o297
78.
Zurück zum Zitat Alcock NW, Harrison WD, Howes C (1984) Secondary bonding. Part 13. Aryl-tellurium(IV) and -iodine(III) acetates and trifluoroacetates. The crystal and molecular structures of bis-(p-methoxyphenyl)tellurium diacetate, µ-oxo-bis[diphenyltrifluoroacetoxytellurium] hydrate, and [bis(trifluoroacetoxy)iodo]benzene. J Chem Soc, Dalton Trans 1709. https://doi.org/10.1039/dt9840001709 Alcock NW, Harrison WD, Howes C (1984) Secondary bonding. Part 13. Aryl-tellurium(IV) and -iodine(III) acetates and trifluoroacetates. The crystal and molecular structures of bis-(p-methoxyphenyl)tellurium diacetate, µ-oxo-bis[diphenyltrifluoroacetoxytellurium] hydrate, and [bis(trifluoroacetoxy)iodo]benzene. J Chem Soc, Dalton Trans 1709. https://​doi.​org/​10.​1039/​dt9840001709
81.
Zurück zum Zitat Patia S, Rappoport Z (eds) (1995) Chemistry of Functional Groups: the chemistry of organic germanium, tin and lead compounds, vol 19. Wiley Patia S, Rappoport Z (eds) (1995) Chemistry of Functional Groups: the chemistry of organic germanium, tin and lead compounds, vol 19. Wiley
82.
Zurück zum Zitat Parr J (2004) Comprehensive coordination chemistry II. In: McCleverty JA, Meye TJ (eds), vol 3. Elsevier Pergamon, Oxford, p 545 Parr J (2004) Comprehensive coordination chemistry II. In: McCleverty JA, Meye TJ (eds), vol 3. Elsevier Pergamon, Oxford, p 545
83.
Zurück zum Zitat Sato T (1995) Comprehensive organometallic chemistry II. In: Abel EW, Stone FGA, Wilkinson G (eds), vol 11. Pergamon Press, Oxford, p 389 Sato T (1995) Comprehensive organometallic chemistry II. In: Abel EW, Stone FGA, Wilkinson G (eds), vol 11. Pergamon Press, Oxford, p 389
84.
Zurück zum Zitat Pinhey JT (1995) Comprehensive organometallic chemistry II. In: Abel EW, Stone FGA, Wilkinson G (eds), vol 11. Pergamon Press, Oxford, p 461 Pinhey JT (1995) Comprehensive organometallic chemistry II. In: Abel EW, Stone FGA, Wilkinson G (eds), vol 11. Pergamon Press, Oxford, p 461
88.
95.
Zurück zum Zitat Karlov SS, Shutov PL, Churakov AV, Lorberth J, Zaitseva GS (2001) New approach to 1-(phenylethynyl)germatranes and 1-(phenylethynyl)-3,7,10-trimethylgermatrane. Reactions of 1-(phenylethynyl)germatrane with N-bromosuccinimide and bromine. J Organomet Chem 627:1–5. https://doi.org/10.1016/S0022-328X(01)00708-2 Karlov SS, Shutov PL, Churakov AV, Lorberth J, Zaitseva GS (2001) New approach to 1-(phenylethynyl)germatranes and 1-(phenylethynyl)-3,7,10-trimethylgermatrane. Reactions of 1-(phenylethynyl)germatrane with N-bromosuccinimide and bromine. J Organomet Chem 627:1–5. https://​doi.​org/​10.​1016/​S0022-328X(01)00708-2
99.
Zurück zum Zitat Kalikhman I, Girshberg O, Lameyer L, Stalke D, Kost D (2001) Tautomeric equilibrium between penta-and hexacoordinate silicon chelates. A chloride bridge between two pentacoordinate silicons. J Am Chem Soc 123:4709–4716. https://doi.org/10.1021/ja004118r Kalikhman I, Girshberg O, Lameyer L, Stalke D, Kost D (2001) Tautomeric equilibrium between penta-and hexacoordinate silicon chelates. A chloride bridge between two pentacoordinate silicons. J Am Chem Soc 123:4709–4716. https://​doi.​org/​10.​1021/​ja004118r
100.
Zurück zum Zitat Taylor PG, Bassindale AR, El Aziz Y, Pourny M, Stevenson R, Hursthouse MB, Coles SJ (2012) Further studies of fluoride ion entrapment in octasilsesquioxane cages; X-ray crystal structure studies and factors that affect their formation. Dalton Trans 41:2048–2059. https://doi.org/10.1039/C1DT11340BCrossRefPubMed Taylor PG, Bassindale AR, El Aziz Y, Pourny M, Stevenson R, Hursthouse MB, Coles SJ (2012) Further studies of fluoride ion entrapment in octasilsesquioxane cages; X-ray crystal structure studies and factors that affect their formation. Dalton Trans 41:2048–2059. https://​doi.​org/​10.​1039/​C1DT11340BCrossRefPubMed
103.
114.
Zurück zum Zitat Esrafili MD, Mohammadian-Sabet F, Baneshi MM (2015) The dual role of halogen, chalcogen, and pnictogen atoms as Lewis acid and base: triangular XBr:SHX:PH2X complexes (X = F, Cl, Br, CN, NC, OH, NH2, and OCH3). Int J Quantum Chem 115:1580–1586. https://doi.org/10.1002/qua.24987CrossRef Esrafili MD, Mohammadian-Sabet F, Baneshi MM (2015) The dual role of halogen, chalcogen, and pnictogen atoms as Lewis acid and base: triangular XBr:SHX:PH2X complexes (X = F, Cl, Br, CN, NC, OH, NH2, and OCH3). Int J Quantum Chem 115:1580–1586. https://​doi.​org/​10.​1002/​qua.​24987CrossRef
132.
144.
Zurück zum Zitat Cangelosi VM, Pitt MA, Vickaryous WJ, Allen CA, Zakharov LN, Johnson DW (2010) Design considerations for the group 15 elements: the pnictogen⋯π interaction as a complementary component in supramolecular assembly design. Cryst Growth Des 10:3531–3536. https://doi.org/10.1021/cg100444nCrossRef Cangelosi VM, Pitt MA, Vickaryous WJ, Allen CA, Zakharov LN, Johnson DW (2010) Design considerations for the group 15 elements: the pnictogen⋯π interaction as a complementary component in supramolecular assembly design. Cryst Growth Des 10:3531–3536. https://​doi.​org/​10.​1021/​cg100444nCrossRef
147.
Zurück zum Zitat Anderson KM, Baylies CJ, Jahan AHMM, Norman NC, Orpen AG, Starbuck J (2003) Coordination complexes of the bismuth(iii) thiolates Bi(SC6F5)3 and Bi(SC6Cl5)3 with pyridineligands. Dalton Trans 3270–3277. https://doi.org/10.1039/B305711A Anderson KM, Baylies CJ, Jahan AHMM, Norman NC, Orpen AG, Starbuck J (2003) Coordination complexes of the bismuth(iii) thiolates Bi(SC6F5)3 and Bi(SC6Cl5)3 with pyridineligands. Dalton Trans 3270–3277. https://​doi.​org/​10.​1039/​B305711A
149.
Zurück zum Zitat Murafuji T, Nagasue M, Tashiro Y, Sugihara Y, Azuma N (2000) Structural characteristics of aryloxybismuthanes stabilized by hypervalent bond formation. Synthesis, incorporation of 4-methoxyphenol through hydrogen bonding, and crystal supramolecularity. Organometallics 19:1003–1007. https://doi.org/10.1021/om9908534 Murafuji T, Nagasue M, Tashiro Y, Sugihara Y, Azuma N (2000) Structural characteristics of aryloxybismuthanes stabilized by hypervalent bond formation. Synthesis, incorporation of 4-methoxyphenol through hydrogen bonding, and crystal supramolecularity. Organometallics 19:1003–1007. https://​doi.​org/​10.​1021/​om9908534
152.
Zurück zum Zitat Nekoueishahraki B, Samuel PP, Roesky HW, Stern D, Matussek J, Stalke D (2012) Organobismuth (III) and dibismuthine complexes bearing N, N′-Disubstituted 1, 8-diaminonaphthalene ligand: synthesis, structure, and reactivity. Organometallics 31:6697–6703. https://doi.org/10.1021/om300758sCrossRef Nekoueishahraki B, Samuel PP, Roesky HW, Stern D, Matussek J, Stalke D (2012) Organobismuth (III) and dibismuthine complexes bearing N, N′-Disubstituted 1, 8-diaminonaphthalene ligand: synthesis, structure, and reactivity. Organometallics 31:6697–6703. https://​doi.​org/​10.​1021/​om300758sCrossRef
154.
Zurück zum Zitat Agocs L, Burford N, Cameron TS, Curtis JM, Richardson JF, Robertson KN, Yhard GB (1996) Spectroscopic, Structural, and Mass spectrometric studies on two systematic series of dithiabismuth(III) heterocycles: identification of bismuthenium cations and their solvent complexes. J Am Chem Soc 118:3225–3232. https://doi.org/10.1021/ja9539756CrossRef Agocs L, Burford N, Cameron TS, Curtis JM, Richardson JF, Robertson KN, Yhard GB (1996) Spectroscopic, Structural, and Mass spectrometric studies on two systematic series of dithiabismuth(III) heterocycles: identification of bismuthenium cations and their solvent complexes. J Am Chem Soc 118:3225–3232. https://​doi.​org/​10.​1021/​ja9539756CrossRef
162.
Zurück zum Zitat Qiu J, Unruh DK, Cozzolino AF (2016) Design, synthesis, and structural characterization of a Bisantimony(III) compound for anion binding and the density functional theory evaluation of halide binding through antimony secondary bonding interactions. J Phys Chem A 120:9257–9269. https://doi.org/10.1021/acs.jpca.6b08170 Qiu J, Unruh DK, Cozzolino AF (2016) Design, synthesis, and structural characterization of a Bisantimony(III) compound for anion binding and the density functional theory evaluation of halide binding through antimony secondary bonding interactions. J Phys Chem A 120:9257–9269. https://​doi.​org/​10.​1021/​acs.​jpca.​6b08170
176.
Zurück zum Zitat Hedidi M, Bentabed-Ababsa G, Derdour A, Roisnel T, Dorcet V, Chevallier F, Picot L, Thiéry V, Mongin F (2014) Synthesis of C, N′-linked bis-heterocycles using a deprotometalation–iodination–N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Bioorg Med Chem 22:3498–3507. https://doi.org/10.1016/j.bmc.2014.04.028CrossRefPubMed Hedidi M, Bentabed-Ababsa G, Derdour A, Roisnel T, Dorcet V, Chevallier F, Picot L, Thiéry V, Mongin F (2014) Synthesis of C, N′-linked bis-heterocycles using a deprotometalation–iodination–N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells. Bioorg Med Chem 22:3498–3507. https://​doi.​org/​10.​1016/​j.​bmc.​2014.​04.​028CrossRefPubMed
177.
Zurück zum Zitat Burk RF (ed) (1994) Selenium in biology and human health. Springer, New York Burk RF (ed) (1994) Selenium in biology and human health. Springer, New York
179.
Zurück zum Zitat Popa RA, Licarete E, Banciu M, Silvestru A (2018) Organoselenium compounds containing pyrazole or phenylthiazole groups: synthesis, structure, tin(IV) complexes and antiproliferative activity. Appl Organomet Chem 32:e4252. https://doi.org/10.1002/aoc.4252 Popa RA, Licarete E, Banciu M, Silvestru A (2018) Organoselenium compounds containing pyrazole or phenylthiazole groups: synthesis, structure, tin(IV) complexes and antiproliferative activity. Appl Organomet Chem 32:e4252. https://​doi.​org/​10.​1002/​aoc.​4252
180.
Zurück zum Zitat Kimura T, Nakahodo T, Fujihara H, Suzuki E (2014) 4,5-Dicyano-3,6-diethylbenzo-1,2-diselenete, a Highly Stable 1,2-Diselenete: its preparation, structural characterization, calculated molecular orbitals, and complexation with tetrakis(triphenylphosphine)palladium. Inorg Chem 53:4411–4417. https://doi.org/10.1021/ic5000765CrossRefPubMed Kimura T, Nakahodo T, Fujihara H, Suzuki E (2014) 4,5-Dicyano-3,6-diethylbenzo-1,2-diselenete, a Highly Stable 1,2-Diselenete: its preparation, structural characterization, calculated molecular orbitals, and complexation with tetrakis(triphenylphosphine)palladium. Inorg Chem 53:4411–4417. https://​doi.​org/​10.​1021/​ic5000765CrossRefPubMed
182.
Zurück zum Zitat Suzuki T, Fujii H, Yamashita Y, Kabuto C, Tanaka S, Harasawa M, Mukai T, Miyashi T (1992) Clathrate formation and molecular recognition by novel chalcogen-cyano interactions in tetracyanoquinodimethanes fused with thiadiazole and selenadiazole rings. J Am Chem Soc 114:3034–3043. https://doi.org/10.1021/ja00034a041CrossRef Suzuki T, Fujii H, Yamashita Y, Kabuto C, Tanaka S, Harasawa M, Mukai T, Miyashi T (1992) Clathrate formation and molecular recognition by novel chalcogen-cyano interactions in tetracyanoquinodimethanes fused with thiadiazole and selenadiazole rings. J Am Chem Soc 114:3034–3043. https://​doi.​org/​10.​1021/​ja00034a041CrossRef
190.
Zurück zum Zitat Neidlein R, Knecht D, Gieren A, Ruiz-Perez C (1987) Synthese und Röntgenstrukturanalyse des Phenanthro[9,10-c]-l,2,5-telluradiazols. Z Naturforschung, B: Chem Sci 42:84–90CrossRef Neidlein R, Knecht D, Gieren A, Ruiz-Perez C (1987) Synthese und Röntgenstrukturanalyse des Phenanthro[9,10-c]-l,2,5-telluradiazols. Z Naturforschung, B: Chem Sci 42:84–90CrossRef
196.
Zurück zum Zitat Murray JS, Politzer P (2009) Molecular surfaces, van der Waals radii and electrostatic potentials in relation to noncovalent interactions. Croat Chem Acta 82:267–275 Murray JS, Politzer P (2009) Molecular surfaces, van der Waals radii and electrostatic potentials in relation to noncovalent interactions. Croat Chem Acta 82:267–275
199.
Zurück zum Zitat Hardegger LA, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, Gsell B, Thoma R, Diez J, Benz J, Plancher JM, Hartmann G, Isshiki Y, Morikami K, Shimma N, Haap W, Banner DW, Diederich F (2011) Halogen bonding at the active sites of human cathepsin L and MEK1 kinase: efficient interactions in different environments ChemMedChem 6:2048–2054. https://doi.org/10.1002/cmdc.201100353 Hardegger LA, Kuhn B, Spinnler B, Anselm L, Ecabert R, Stihle M, Gsell B, Thoma R, Diez J, Benz J, Plancher JM, Hartmann G, Isshiki Y, Morikami K, Shimma N, Haap W, Banner DW, Diederich F (2011) Halogen bonding at the active sites of human cathepsin L and MEK1 kinase: efficient interactions in different environments ChemMedChem 6:2048–2054. https://​doi.​org/​10.​1002/​cmdc.​201100353
210.
Zurück zum Zitat Bikbaeva ZM, Ivanov DM, Novikov AS, Ananyev IV, Bokach NA, Kukushkin VY (2017) Electrophilic–nucleophilic dualism of Nickel(II) toward Ni⋯I noncovalent interactions: semicoordination of iodine centers via electron belt and halogen bonding via σ-hole. Inorg Chem 56:13562–13578. https://doi.org/10.1021/acsinorgchem7b02224 Bikbaeva ZM, Ivanov DM, Novikov AS, Ananyev IV, Bokach NA, Kukushkin VY (2017) Electrophilic–nucleophilic dualism of Nickel(II) toward Ni⋯I noncovalent interactions: semicoordination of iodine centers via electron belt and halogen bonding via σ-hole. Inorg Chem 56:13562–13578. https://​doi.​org/​10.​1021/​acsinorgchem7b02​224
211.
Zurück zum Zitat Rozhkov AV, Eliseeva AA, Baykov SV, Galmés B, Frontera A, Kukushkin VY (2020) One-Pot Route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F Functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. Cryst Growth Des 20:5908–5921. https://doi.org/10.1021/acs.cgd.0c00606CrossRef Rozhkov AV, Eliseeva AA, Baykov SV, Galmés B, Frontera A, Kukushkin VY (2020) One-Pot Route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F Functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding. Cryst Growth Des 20:5908–5921. https://​doi.​org/​10.​1021/​acs.​cgd.​0c00606CrossRef
213.
Zurück zum Zitat Gossage RA, Ryabov AD, Spek AL, Stufkens DJ, van Beek JAM, van Eldik R, van Koten G (1999) Models for the initial stages of oxidative addition. Synthesis, characterization, and mechanistic investigation of η1-I2 organometallic “Pincer” complexes of platinum. X-ray crystal structures of [PtI(C6H3{CH2NMe2}2–2,6)(η1-I2)] and exo-meso-[Pt(η1-I3)(η1-I2)(C6H3{CH2N(t-Bu)Me}2–2,6)]. J Am Chem Soc 121:2488–2497. https://doi.org/10.1021/ja982095z Gossage RA, Ryabov AD, Spek AL, Stufkens DJ, van Beek JAM, van Eldik R, van Koten G (1999) Models for the initial stages of oxidative addition. Synthesis, characterization, and mechanistic investigation of η1-I2 organometallic “Pincer” complexes of platinum. X-ray crystal structures of [PtI(C6H3{CH2NMe2}2–2,6)(η1-I2)] and exo-meso-[Pt(η1-I3)(η1-I2)(C6H3{CH2N(t-Bu)Me}2–2,6)]. J Am Chem Soc 121:2488–2497. https://​doi.​org/​10.​1021/​ja982095z
215.
Zurück zum Zitat Baykov SV, Dabranskaya U, Ivanov DM, Novikov AS, Boyarskiy VP (2018) Pt/Pd and I/Br isostructural exchange provides formation of C–I⋯Pd, C–Br⋯Pt, and C–Br⋯Pd metal-involving halogen bonding. Cryst Growth Des 18:5973–5980. https://doi.org/10.1021/acs.cgd.8b00762 Baykov SV, Dabranskaya U, Ivanov DM, Novikov AS, Boyarskiy VP (2018) Pt/Pd and I/Br isostructural exchange provides formation of C–I⋯Pd, C–Br⋯Pt, and C–Br⋯Pd metal-involving halogen bonding. Cryst Growth Des 18:5973–5980. https://​doi.​org/​10.​1021/​acs.​cgd.​8b00762
216.
Zurück zum Zitat Bulatova M, Ivanov DM, Haukka M (2021) Classics meet classics: theoretical and experimental studies of halogen bonding in adducts of Platinum(II) 1,5-cyclooctadiene halide complexes with diiodine, iodoform, and 1,4-diiodotetrafluorobenzene. Cryst Growth Des 21:974–987. https://doi.org/10.1021/acs.cgd.0c01314CrossRef Bulatova M, Ivanov DM, Haukka M (2021) Classics meet classics: theoretical and experimental studies of halogen bonding in adducts of Platinum(II) 1,5-cyclooctadiene halide complexes with diiodine, iodoform, and 1,4-diiodotetrafluorobenzene. Cryst Growth Des 21:974–987. https://​doi.​org/​10.​1021/​acs.​cgd.​0c01314CrossRef
Metadaten
Titel
Supramolecular Assemblies Based on σ-hole Interactions
verfasst von
Antonio Bauzá
Antonio Frontera
Copyright-Jahr
2022
DOI
https://doi.org/10.1007/978-3-031-00657-9_7

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.