The Relation between Bond Lengths and Dissociation Energies of Carbon−Carbon Bonds

Zavitsas, Andreas A.

doi:10.1021/jp0269367

Cited by 187 publications

(139 citation statements)

References 13 publications

Supporting

Mentioning

123

Contrasting

Unclassified

Order By: Relevance

“…Beyond this point, the ultimate separation occurs when the interatomic distance between the last two bonded C-C atoms exceeds 1.75 Å. From the literature [43], it was found that, 1.75 Å is the maximum possible bond length between the two carbon atoms which is found consistent with the current observation.…”

Section: Simulation Analysissupporting

confidence: 91%

See 1 more Smart Citation

Influence of test methodology and probe geometry on nanoscale fatigue failure of diamond-like carbon film

Faisal

Ahmed

Goel

et al. 2014

Surface and Coatings Technology

View full text Add to dashboard Cite

Section: Simulation Analysissupporting

confidence: 91%

“…Although the quantitative measure of separation distance [43] of C-C bond of 1.75 Å provide confidence in the MD simulation, authors also conducted an evaluation of the modulus of elasticity from the loading and unloading curve shown in Fig. 11.…”

Section: Simulation Analysismentioning

confidence: 99%

Influence of test methodology and probe geometry on nanoscale fatigue failure of diamond-like carbon film

Faisal

Ahmed

Goel

et al. 2014

Surface and Coatings Technology

View full text Add to dashboard Cite

“…Angewandte empirische Bindungslänge-Bindungsstärke-Korrelationen, [148] die üblicherweise exzellent für Kohlenwasserstoffe greifen: Vonk urzen Bindungen denkt man, dass sie stärker sind als lange Bindungen, [149] wie bereits 1960 von Pauling [150] und später erneut beschrieben. [148] Die Herstellung einer Serie gekuppelter Diamantoid(hetero)dimere brachte im Falle des 2-(1-Diamantyl) [121]tetramantans( Abbildung 8, links) sterisch stark überfrachtete Strukturen mit außerordentlich langen zentralen C-C-Bindungen von bis zu 1.707 h ervor.…”

Section: London'sche Dispersionunclassified

“…[148] Die Herstellung einer Serie gekuppelter Diamantoid(hetero)dimere brachte im Falle des 2-(1-Diamantyl) [121]tetramantans( Abbildung 8, links) sterisch stark überfrachtete Strukturen mit außerordentlich langen zentralen C-C-Bindungen von bis zu 1.707 h ervor. Dies ist die längste publizierte C-C-Bindung in einem reinen Alkan (längere C-C-Bindungen von bis zu 1.78 wurden für Strukturen mit Heteroatomen beschrieben [151] ).…”

Section: London'sche Dispersionunclassified

London’sche Dispersionswechselwirkungen in der Molekülchemie – eine Neubetrachtung sterischer Effekte

2015

View full text Add to dashboard Cite

Die London’sche Dispersion, die den attraktiven Teil des Van‐der‐Waals‐Potentials beschreibt, wurde lange als Element struktureller Stabilität in der molekularen Chemie unterschätzt. Als solches beeinflusst sie auch entscheidend die chemische Reaktivität und Katalyse. Ihre Vernachlässigung ist auf die Annahme zurückzuführen, dass die Dispersionswechselwirkung schwach sei, was nur für eine einzelne paarweise Wechselwirkung zweier Atome stimmt. Für Strukturen zunehmender Größe kann die gesamte Dispersionsstabilisierung mehrere zehn kcal mol−1 betragen. Dieser Aufsatz soll die Wichtigkeit inter‐ und intramolekularer Dispersion anhand von Beispielen für die erste Vollperiode verdeutlichen. Die Synergie aus Experiment und Theorie hat ein Niveau erreicht, auf dem Dispersionseffekte sehr genau verstanden werden können. Als Konsequenz daraus werden wir wohl unser Verständnis bezüglich sterischer Hinderung und stereoelektronischer Effekte überdenken müssen. Die Quantifizierung von Dispersionsenergiedonoren wird unsere Fähigkeiten verbessern, komplexe molekulare Strukturen und Katalysatoren zu entwickeln.

show abstract

“…Based on a database study, Zavitsas expected that the covalent bond dissociation energy (BDE) would be diminished at a distance greater than 1.75 ¡ by assuming a negative-sloped linear correlation between BDE and the bond distance. 3 Adcock reported that the shortest nonbonded C£C contact was 1. 8 ¡, 4 which suggests that the CC bond length might have a limit of around 1.8 ¡.…”

Section: ¹1mentioning

confidence: 99%

Hexaphenylethanes with an Ultralong C–C Bond: Expandability of the C–C Bond in Highly Strained Tetraarylpyracenes

et al. 2013

View full text Add to dashboard Cite

Over the past few decades, many studies have been conducted on ultralong CC bonds (bond length greater than 1.7 ¡). This highlight review discusses the molecular design of ultralong CC bonds and their bonding properties, especially their "expandability." In particular, the ultralong CC bonds in tetraarylpyracene derivatives can change in length by adopting a slightly different conformation in the crystalline state. This expandability of ultralong CC bonds could be due to the smaller decrease in bond energy at a longer interatomic distance (>1.7 ¡). This interesting property can be applied to stimulusresponsive materials, as illustrated in the thermochromism of a bis(methylacridan)-substituted pyracene crystal, since the thermally induced change in bond-length modifies the HOMO LUMO gap. Ç IntroductionA better understanding of the nature of covalent bonds is important because covalent bonding is a fundamental concept in chemistry. The comparison of "normal" bonds and bonds with an unusual parameter, such as bond length or angle, is an important method for gaining insight into covalent bonds. There have been many studies based on this idea, especially on the CC single bond, which is one of the most common covalent bonds in organic compounds. Thus, the investigation of its properties should provide significant information on covalent bonds. A CC single bond is very stable and has a high bond energy (ca. 100 kcal mol ¹1) and a standard bond length (1.54 ¡) and bond angle (109.5°).1 Compounds with unusual CC bond lengths or CCC bond angles have been synthesized to investigate whether they exhibit special properties or reactivities. Propellanes are known to have CC bonds with unusual bond angles. Shorter CC bonds have also been of interest, and Sekiguchi et al. reported a very short CC single bond in tetrahedranyltetrahedrane. 2It is unclear how far a CC single bond can be stretched: i.e., at what point does a CC single bond separate into two carbon radicals? Based on a database study, Zavitsas expected that the covalent bond dissociation energy (BDE) would be diminished at a distance greater than 1.75 ¡ by assuming a negative-sloped linear correlation between BDE and the bond distance.3 Adcock reported that the shortest nonbonded C£C contact was 1.8 ¡, 4 which suggests that the CC bond length might have a limit of around 1.8 ¡. However, when we consider that the bond length of a covalent bond is determined by the balance between the stabilization energy obtained by the sharing of electrons and the repulsive force generated by two positively charged atomic nuclei, the LennardJones potential may be more appropriate than a simple linear correlation. Thus, the change in BD with an increase in the length of prestrained CC bonds (1.61.7 ¡) should be smaller than the energy required to lengthen a normal CC bond (1.54 ¡) to the same degree. Thus, it is highly likely that we can find a CC bond longer than that described Zavitsas before the bond is degraded.This highlight review briefly describes previous studies on he...

show abstract

The Relation between Bond Lengths and Dissociation Energies of Carbon−Carbon Bonds

Cited by 187 publications

References 13 publications

Influence of test methodology and probe geometry on nanoscale fatigue failure of diamond-like carbon film

Influence of test methodology and probe geometry on nanoscale fatigue failure of diamond-like carbon film

London’sche Dispersionswechselwirkungen in der Molekülchemie – eine Neubetrachtung sterischer Effekte

Hexaphenylethanes with an Ultralong C–C Bond: Expandability of the C–C Bond in Highly Strained Tetraarylpyracenes

Contact Info

Product

Resources

About