A body-diagonal bond in cubane: can it be introduced?

Hassenrück, Karin; Radziszewski, Juliusz G.; Balaji, V.; Murthy, G. Sreenivasa; McKinley, Allan J.; David, Donald E.; Lynch, Vincent M.; Martin, H.; Michl, Josef

doi:10.1021/ja00158a061

Cited by 47 publications

(40 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…27,28 All reagents were purchased from Merck chemical company and used without further purication. 27,28 All reagents were purchased from Merck chemical company and used without further purication.…”

Section: Methodsmentioning

confidence: 99%

Preparation of cubane-1,4-dicarboxylate–Zn–Al layered double hydroxide nanohybrid: comparison of structural and optical properties between experimental and calculated results

Rad

Rezvani

2015

RSC Adv.

View full text Add to dashboard Cite

In the present research, we report cubane-1,4-dicarboxylate anions (cuban-dc) assembled into a Zn 2 Al layered double hydroxide (LDH) inorganic host using the coprecipitation method, in which solutions of Zn(II) and Al(III) nitrate salts react with an alkaline solution of cubane-1,4-dicarboxylic acid. Powder X-ray diffraction, FTIR spectroscopy, elemental analyses, and thermal gravimetric analysis (TGA) were used to characterize the successful incorporation of the cubane-1,4-dicarboxylate anions into the interlayer space of LDH. Periodic density functional theory was employed to understand the structural and electronic properties of the cubane-dc-Zn 2 Al-LDH system. The quantum mechanics study was supported by periodic density functional theory (DFT) calculation which predicts appropriate values for structural and optical properties of cubane-dc-Zn 2 Al-LDH. Optical and structural theoretical results are in good agreement with the experimental results, which show that when cubane-1,4-dicarboxylate anions intercalate in Zn-Al-LDH, they cause a red shift and subsequently decrease the band gap energy in comparison with LDHs that contain small anions. Fig. 7 The calculated (solid line) and experimental (dashed line) X-ray diffraction patterns of cubane-dc-Zn-Al-LDH.This journal is

show abstract

Section: Methodsmentioning

confidence: 99%

Preparation of cubane-1,4-dicarboxylate–Zn–Al layered double hydroxide nanohybrid: comparison of structural and optical properties between experimental and calculated results

Rad

Rezvani

2015

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…The same behavior is observed for tetrahedrane and dodecahedrane, but not for cubane, whose dimerization is favored by 9 kJ/mol. In fact, the stability of covalently bonded cubanes was experimentally proved through the synthesis and crystallographic characterization of cubylcubane in 1988 . Alternatively, Prinzbach et al were able to dimerize C 20 dodecahedranes by the formation of two CC bonds in the way to a C 40 cage .…”

Section: Computational Analysismentioning

confidence: 99%

Intermolecular interactions in group 14 hydrides: Beyond CH···HC contacts

2017

View full text Add to dashboard Cite

In line with previous work in which we established the factors that enhance attractive CH···HC dihydrogen interactions in alkanes, an extended theoretical analysis of noncovalent intermolecular interactions in group 14 hydrides is presented here. Remarkably, these weak interactions may play a major role in determining the crystal structures adopted by several families of molecules. A combined structural and computational analysis at the MP2 level allowed us to identify and characterize different interactions of the type EH···HE and E···HE (E = Si, Ge, Sn, and Pb), and to find also the most suitable scenario for the establishment of each particular type. The nature of the interactions has been analyzed in terms of natural charges of the atoms involved and a topological analysis of the electron density of several dimers confirms the existence of H···H and H···E attractive contacts. We have observed that the interaction strength increases when descending down the periodic group and that silicon has a marked tendency to establish Si···HSi interactions. A size‐dependent backbone effect that reinforces H···H dihydrogen interactions in polyhedral systems has also been found.

show abstract

“…The 2.635 Å for the 1,4-CϪC distance of singlet-6 is clearly too long to call it a bond; [34] this is in agreement with the unsuccessful attempts in preparing 6c. [41] All other CϪC bond lengths in the three isomers (in either spin state) are quite normal single bonds (compared to the parent cubane) and lie between 1.5Ϫ1.6 Å .…”

Section: Resultsmentioning

confidence: 94%

“…[34] Trapping products derived from 6o or just its monoradical precursor were observed. [41] Hence, while 4 is a closed-shell molecule and while it paral-lels the findings for 1 in terms of electronic coupling, the singlet-triplet gap for the 1,4 derivative 6 is still substantial, unlike the results for its aromatic cousin 3. Again, the most critical structure is 5, for which we now have a method of preparation at hand starting from 1,3-diiodocubane, [42] which itself can be synthesized by our recently introduced phase-transfer catalytic alkane halogenation protocol that is described in detail elsewhere.…”

mentioning

confidence: 80%

See 1 more Smart Citation

A REKS Assessment of the Face‐Diagonal Bond in 1,3‐Didehydrocubane and a Comparison with Benzyne Biradicals

et al. 2003

View full text Add to dashboard Cite

Keywords: Density functional calculations / Radicals / Benzynes / Through-space interactions / Through-bond interactionsThe three isomeric cubane biradicals were studied using spin-restricted ensemble-referenced Kohn−Sham (REKS) density functional calculations at the B3LYP/6-31G(d) level of theory. The most stable biradical was found to be orthocubene with the meta-cubene and para-cubene biradicals 4.7 kcal mol −1 and 17.8 kcal mol −1 higher in energy, respectively. The singlet ground states are well separated from their lowest lying triplet states. These singlet-triplet energy differences mostly originate from through-space interactions for

show abstract

A body-diagonal bond in cubane: can it be introduced?

Cited by 47 publications

References 1 publication

Preparation of cubane-1,4-dicarboxylate–Zn–Al layered double hydroxide nanohybrid: comparison of structural and optical properties between experimental and calculated results

Preparation of cubane-1,4-dicarboxylate–Zn–Al layered double hydroxide nanohybrid: comparison of structural and optical properties between experimental and calculated results

Intermolecular interactions in group 14 hydrides: Beyond CH···HC contacts

A REKS Assessment of the Face‐Diagonal Bond in 1,3‐Didehydrocubane and a Comparison with Benzyne Biradicals

Contact Info

Product

Resources

About