Diego M. Andrada

Saarland University

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Gernot Frenking

Nanjing Tech University

121

Rajendra S. Ghadwal

Bielefeld University

Beate Neumann

Bielefeld University

Dennis Rottschäfer

Bielefeld University

Herbert W. Roesky

University of Göttingen

Dietmar Stalke

University of Göttingen

Hans‐Georg Stammler

Bielefeld University

Bernd Morgenstern

Saarland University

Regine Herbst‐Irmer

University of Göttingen

Tetiana Sergeieva

Saarland University

Cooperative Institutions

University of Göttingen

Institute of Inorganic Chemistry of the Slovak Academy of Sciences

Saarland University

Universidad Nacional de Córdoba

Consejo Nacional de Investigaciones Científicas y Técnicas

Philipps University of Marburg

Universitätsmedizin Göttingen

Chinese Academy of Sciences

Robert Bosch (Germany)

Centre National de la Recherche Scientifique

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Photoinduced nucleophilic substitution of iodocubanes with arylthiolate and diphenylphosphanide ions. Experimental and computational approaches

RSC Advances (2018)

Liliana Jiménez Marcelo Puiatti Diego M. Andrada Federico I. Brigante Karina F. Crespo Andrada

A new synthetic route to modify the cubane nucleus is reported here. Methyl-4-iodocubane-1-carboxylate (1) and 1,4-diiodocubane (2) were employed as reagents to react with arylthiolate and diphenylphosphanide ions under irradiation in liquid ammonia and dimethylsulphoxide. The reactions proceed to afford thioaryl- and diphenylphosphoryl- cubane derivatives in moderate to good yields. It is also found that the monosubstituted product with retention of the second iodine is an intermediate compound. Mechanistic aspects are supported by DFT calculations.

Cubane

Liquid ammonia

Carboxylate

10.1039/c8ra06275g

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Citations (4)

CCDC 951807: Experimental Crystal Structure Determination

The Cambridge Structural Database (2014)

Fabian Dielmann Diego M. Andrada Gernot Frenking Guy Bertrand

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc10yfgv

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Citations (0)

CCDC 2271528: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Chantsalmaa Berthold Matthias Müller Sergei I. Ivlev Diego M. Andrada Magnus R. Buchner

10.5517/ccdc.csd.cc2g7q3k

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Dativeversuselectron-sharing bonding in N-oxides and phosphane oxides R₃EO and relative energies of the R₂EOR isomers (E = N, P; R = H, F, Cl, Me, Ph). A theoretical study

Physical Chemistry Chemical Physics (2018)

Tao Yang Diego M. Andrada Gernot Frenking

Quantum chemical calculations using ab initio methods at the CCSD(T)/def2-TZVPP level and density functional theory using BP86 and M06-2X functionals in conjunction with def2-TZVPP basis sets have been carried out on the title molecules. The calculated energies suggest that the N-oxides R3NO with R = F, Cl are lower in energy than the amine isomers R2NOR, but the latter form is more stable than the N-oxides when R = H, Me, Ph. In contrast, the phosphane oxides R3PO are always more stable than the phosphanyl isomers R2NOR except for the parent system with R = H, where the two isomers are close in energy. The energy decomposition analysis suggests that the best description of the N-O bond in N-oxides R3NO depends on the nature of the substituent R. The halogen systems F3NO and Cl3NO and the triphenyl species Ph3NO possess dative bonds R3N→O, which are enhanced by R3N←O π backdonation. The contribution of the π backdonation is only 10% of the total orbital interactions ΔEorb in Ph3NO, but it amounts to ∼22% of ΔEorb in F3NO and Cl3NO. The N-O bonds H3NO and Me3NO are better described in terms of electron-sharing single bonds between charged fragments R3N+-O-, which are supported by modest R3N+←O- π backdonation that comprise 13-16% of ΔEorb. In contrast, all phosphane oxides R3PO are best depicted with electron-sharing single bonds between charged fragments R3P+-O-, which are significantly supported by R3P+←O- π backdonation contributing 22-32% of ΔEorb.

Atoms in molecules

10.1039/c8cp00951a

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Citations (38)

Kristalline Anionen auf Basis klassischer N‐Heterocyclischer Carbene

Angewandte Chemie (2022)

Arne Merschel Dennis Rottschäfer Beate Neumann Hans‐Georg Stammler Mark R. Ringenberg

Abstract Die ersten stabilen Anionen K[SIPr Bp ] ( 4 a‐K ) und K[IPr Bp ] ( 4 b‐K ) (SIPr Bp =BpC{N(Dipp)CH 2 } 2 , IPr Bp =BpC{N(Dipp)CH} 2 ; Bp=4‐PhC 6 H 4 ; Dipp=2,6‐ i Pr 2 C 6 H 3 ), die von klassischen N‐heterocyclischen Carbenen (NHCs) abgeleitet sind (d. h. SIPr und IPr), wurden als violette kristalline Feststoffe isoliert. 4 a‐K und 4 b‐K wurden durch die Reduktion der neutralen Radikale [SIPr Bp ] ( 3 a ) bzw. [IPr Bp ] ( 3 b ) mit KC 8 hergestellt. Die Radikale 3 a und 3 b sowie [Me‐IPr Bp ] ( 3 c ) (Me−IPr Bp =BpC{N(Dipp)CMe} 2 ) liegen als kristalline Feststoffe vor, wenn die entsprechenden 1,3‐Imidazoli(ni)umbromide (SIPr Bp )Br ( 2 a ), (IPr Bp )Br ( 2 b ) und (Me‐IPr Bp )Br ( 2 c ) mit KC 8 umgesetzt werden. Die Cyclovoltammogramme von 2 a – 2 c zeigen zwei reversible Ein‐Elektronen‐Redoxprozesse im Bereich von −0.5 bis −2.5 V, die den Radikalen 3 a – 3 c und den Anionen ( 4 a – 4 c ) − entsprechen. Quantenchemische Berechnungen deuten auf einen geschlossenschaligen Singulett‐Grundzustand für ( 4 a – 4 c ) − mit einer Singulett‐Triplett‐Energielücke von 17–24 kcal mol −1 hin.

10.1002/ange.202215244

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Carbodicarbenes: Unexpected π-Accepting Ability during Reactivity with Small Molecules

Journal of the American Chemical Society (2017)

Wen‐Ching Chen Wei‐Chih Shih Titel Jurca Lili Zhao Diego M. Andrada

An investigation of carbodicarbenes, the less explored member of the carbenic complex/ligand family has yielded unexpected electronic features and concomitant reactivity. Observed 1,2-addition of E-H bonds (E = B, C, Si) across the carbone central carbon and that of the flanking N-heterocyclic carbene (NHC) fragment, combined with single-crystal X-ray studies of a model Pd complex strongly suggests a significant level of π-accepting ability at the central carbon of the NHC moiety. This feature is atypical of classic NHCs, which are strong σ-donors, with only nominal π-accepting ability. The unanticipated π-acidity is critical for engendering carbodicarbenes with reactivity more commonly observed with frustrated Lewis pairs (FLPs) rather than the more closely related NHCs and cyclic (alkyl)(amino)carbenes (CAACs).

Reactivity

Moiety

Frustrated Lewis pair

Carbon fibers

10.1021/jacs.7b08031

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Citations (70)

Organosilicon Radicals with Si–H and Si–Me Bonds from Commodity Precursors

Journal of the American Chemical Society (2017)

Subrata Kundu Prinson P. Samuel Soumen Sinhababu Anna V. Luebben Birger Dittrich

The cyclic alkyl(amino) carbene (cAAC) stabilized biradicals of composition (cAAC)2SiH2 (1), (cAAC)SiMe2-SiMe2(cAAC) (2), and (cAAC)SiMeCl-SiMeCl(cAAC) (3) have been isolated as molecular species. All the compounds are stable at room temperature for more than 6 months under inert conditions in the solid state. All radical species were fully characterized by single-crystal X-ray structure analysis and EPR spectroscopy. Furthermore, the structure and bonding of compounds 1-3 have been investigated by theoretical methods. Compound 1 contains the SiH2 moiety and this is the first instance, where we have isolated 1 without an acceptor molecule.

Organosilicon

Moiety

Inert

Inert gas

Acceptor

10.1021/jacs.7b06610

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Citations (28)

CCDC 1812388: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Dennis Rottschäfer Nga Kim T. Ho Beate Neumann Hans‐Georg Stammler Maurice van Gastel

10.5517/ccdc.csd.cc1yty4v